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UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

FORM 10-Q

[x] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934
For the quarterly period ended June 30, 2018

or
 
[ ] TRANSITION REPORT PURSUANT TO SECTION 13 OF 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934
For the transition period from______ to ______
 
Commission File Number: 001-36330
CASTLIGHT HEALTH, INC.
(Exact name of registrant as specified in its charter)

			
Delaware
(State or other jurisdiction of
incorporation or organization)	 	26-1989091
(I.R.S. Employer
Identification Number)	

150 Spear Street, Suite 400
San Francisco, CA 94105
(Address of principal executive offices)
(415) 829-1400
(Registrant’s telephone number, including area code)

Indicate by check-mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15 (d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports) and (2) has been subject to such filing requirements for the past 90 days. Yes [X] No []

Indicate by check mark whether the registrant has submitted electronically and posted on its corporate Web site, if any, every Interactive Data File required to be submitted and posted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit and post such files). Yes [X] No [ ]

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

					
Large accelerated filer [ ]	Accelerated filer [X]	Non-accelerated filer [ ]
(Do not check if a smaller
reporting company)	Smaller reporting company [ ]	Emerging growth company [X]	

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. [X]

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act). Yes[ ] No [X]

As of July 27, 2018 , there were 51,923,213 shares of the Company’s Class A common stock outstanding and 85,836,963 shares of the Company’s Class B common stock outstanding.

Table of Contents

TABLE OF CONTENTS

	
			
 	 	Page	
 	PART I. Financial Information	1	
Item 1.	Financial Statements  	1	
 	Condensed Consolidated Balance Sheets as of June 30, 2018 and December 31, 2017	1	
 	Condensed Consolidated Statements of Operations for the three and six months ended June 30, 2018 and 2017	2	
 	Condensed Consolidated Statements of Comprehensive Loss for the three and six months ended June 30, 2018 and 2017	3	
 	Condensed Consolidated Statements of Cash Flows for the six months ended June 30, 2018 and 2017	4	
 	Notes to Condensed Consolidated Financial Statements	5	
Item 2.	Management’s Discussion and Analysis of Financial Condition and Results of Operations	23	
Item 3.	Quantitative and Qualitative Disclosures About Market Risk	31	
Item 4.	Controls and Procedures	32	
 	PART II. Other Information	32	
Item 1.	Legal Proceedings	32	
Item 1A.	Risk Factors	33	
Item 6.	Exhibits	55	
 	Signature	56	
______________________________________

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PART I. FINANCIAL INFORMATION
Item 1. Financial Statements

CASTLIGHT HEALTH, INC.
CONDENSED CONSOLIDATED BALANCE SHEETS
(In thousands)
(unaudited)

								
 	As of	
 	June 30, 2018	 	December 31, 2017	
 		 	 (as adjusted) (1)	
Assets	 	 	 	
Current assets:	 	 	 	
Cash and cash equivalents	$	44,642		 	$	61,319		
Marketable securities	29,833		 	32,025		
Accounts receivable and other, net	28,184		 	21,933		
Prepaid expenses and other current assets	5,742		 	3,991		
Total current assets	108,401		 	119,268		
Property and equipment, net	5,247		 	5,263		
Restricted cash, non-current	1,325		 	1,325		
Deferred commissions	24,691		 	27,512		
Deferred professional service costs	11,855		 	12,480		
Intangible assets, net	18,144		 	20,253		
Goodwill	91,785		 	91,785		
Other assets	2,141		 	1,997		
Total assets	$	263,589		 	$	279,883		
Liabilities and stockholders’ equity	 	 	 	
Current liabilities:	 	 	 	
Accounts payable	$	4,619		 	$	3,907		
Accrued expenses and other current liabilities	17,829		 	13,178		
Accrued compensation	9,530		 	13,941		
Deferred revenue	26,509		 	25,985		
Total current liabilities	58,487		 	57,011		
Deferred revenue, non-current	2,723		 	4,457		
Debt, non-current	4,183		 	4,958		
Other liabilities, non-current	2,964		 	1,900		
Total liabilities	68,357		 	68,326		
Commitments and contingencies		 		
Stockholders’ equity:	 	 	 	
Class A and Class B common stock	14		 	13		
Additional paid-in capital	598,963		 	586,900		
Accumulated other comprehensive loss	(9	)	 	(22	)	
Accumulated deficit	(403,736	)	 	(375,334	)	
Total stockholders’ equity	195,232		 	211,557		
Total liabilities and stockholders’ equity	$	263,589		 	$	279,883		
(1) Prior-period information has been adjusted for the adoption of ASU No. 2014-09, Revenue from Contracts with Customers (“ASC 606”). See Note 2 – Accounting Standards and Significant Accounting Policies for a summary of adjustments.
See Notes to Condensed Consolidated Financial Statements.

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CASTLIGHT HEALTH, INC.
CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS
(In thousands, except per share data)
(unaudited)

	
																
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	2017	 	2018	 	2017	
 	 	 	 (as adjusted) (1)	 	 	 	 (as adjusted) (1)	
Revenue:	 	 	 	 	 	 	 	
Subscription	$	34,802		 	$	30,382		 	$	67,791		 	$	56,279		
Professional services and other	2,982		 	2,250		 	6,472		 	4,056		
Total revenue, net	37,784		 	32,632		 	74,263		 	60,335		
Cost of revenue:	 	 	 	 	 	 	 	
Cost of subscription (2)	9,140		 	7,706		 	18,314		 	11,952		
Cost of professional services and other (2)	6,590		 	4,628		 	12,359		 	8,437		
Total cost of revenue	15,730		 	12,334		 	30,673		 	20,389		
Gross profit	22,054		 	20,298		 	43,590		 	39,946		
Operating expenses:	 	 	 	 	 	 	 	
Sales and marketing  (2)	13,306		 	15,935		 	27,218		 	30,081		
Research and development (2)	16,425		 	15,194		 	31,796		 	26,265		
General and administrative (2)	6,382		 	6,766		 	13,207		 	15,764		
Total operating expenses	36,113		 	37,895		 	72,221		 	72,110		
Operating loss	(14,059	)	 	(17,597	)	 	(28,631	)	 	(32,164	)	
Other income, net	101		 	12		 	229		 	205		
Loss before income tax benefit	$	(13,958	)	 	$	(17,585	)	 	$	(28,402	)	 	(31,959	)	
Income tax benefit	—		 	(5,206	)	 	—		 	(5,206	)	
Net loss	$	(13,958	)	 	$	(12,379	)	 	$	(28,402	)	 	$	(26,753	)	
Net loss per share, basic and diluted	$	(0.10	)	 	$	(0.09	)	 	$	(0.21	)	 	$	(0.23	)	
Weighted-average shares used to compute basic and diluted net loss per share	136,682		 	130,537		 	135,843		 	117,807		
_______________________
(1) Prior-period information has been adjusted for the adoption of ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies for a summary of adjustments.
(2) Includes stock-based compensation expense as follows:

																
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	2017	 	2018	 	2017	
 	 	 	 (as adjusted) (1)	 	 	 	(as adjusted) (1)	
Cost of revenue:	 	 	 	 	 	 	 	
Cost of subscription	$	231		 	$	253		 	$	473		 	$	380		
Cost of professional services and other	315		 	363		 	616		 	609		
Sales and marketing	1,318		 	2,441		 	2,456		 	4,595		
Research and development	1,908		 	2,254		 	3,562		 	4,044		
General and administrative	1,375		 	1,169		 	2,632		 	2,464		
_______________________
(1) Prior-period information has been adjusted for the adoption of ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies for a summary of adjustments.
See Notes to Condensed Consolidated Financial Statements.

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CASTLIGHT HEALTH, INC
CONDENSED CONSOLIDATED STATEMENTS OF COMPREHENSIVE LOSS
(In thousands)
(unaudited)

																
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	2017	 	2018	 	2017	
 	 	 	 (as adjusted) (1)	 	 	 	 (as adjusted) (1)		
Net loss	$	(13,958	)	 	$	(12,379	)	 	$	(28,402	)	 	$	(26,753	)	
Other comprehensive income (loss):	 	 	 	 	 	 	 	
Net change in unrealized gain (loss) on available-for-sale marketable securities	11		 	4		 	13		 	(15	)	
Other comprehensive income (loss)	11		 	4		 	13		 	(15	)	
Comprehensive loss	$	(13,947	)	 	$	(12,375	)	 	$	(28,389	)	 	$	(26,768	)	
_______________________
(1) Prior-period information has been adjusted for ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies for a summary of adjustments.

See Notes to Condensed Consolidated Financial Statements.

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CASTLIGHT HEALTH, INC.
CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS
(In thousands)
(unaudited)

								
 	Six Months Ended June 30,	
 	2018	 	2017	
 	 	 	 (as adjusted) (1)	
Operating activities:	 	 	 	
Net loss	$	(28,402	)	 	$	(26,753	)	
Adjustments to reconcile net loss to net cash used in operating activities:	 	 	 	
Depreciation and amortization	3,573		 	2,758		
Stock-based compensation	9,739		 	12,092		
Amortization of deferred commissions	5,800		 	4,289		
Amortization of deferred professional service costs	2,097		 	1,958		
Lease exit and related charges	1,817		 	—		
Release of deferred tax valuation allowance due to business combination	—		 	(5,206	)	
Change in fair value of contingent consideration liability	—		 	(643	)	
Accretion and amortization of marketable securities	(266	)	 	84		
Changes in operating assets and liabilities:	 	 	 	
Accounts receivable and other, net	(6,252	)	 	(3,117	)	
Deferred commissions	(2,979	)	 	(3,452	)	
Deferred professional service costs	(1,389	)	 	(1,853	)	
Prepaid expenses and other assets	(1,896	)	 	(859	)	
Accounts payable	511		 	(508	)	
Accrued expenses and other liabilities	(1,229	)	 	(527	)	
Deferred revenue	(1,210	)	 	6,711		
Net cash used in operating activities	(20,086	)	 	(15,026	)	
Investing activities:	 	 	 	
Purchase of property and equipment	(1,304	)	 	(930	)	
Purchase of marketable securities	(23,979	)	 	(31,775	)	
Maturities of marketable securities	26,450		 	63,737		
Business combination, net of cash acquired	—		 	(2,264	)	
Net cash provided by investing activities	1,167		 	28,768		
Financing activities:	 	 	 	
Proceeds from exercise of stock options	2,242		 	831		
Payments of issuance costs related to equity	—		 	(731	)	
Net cash provided by financing activities	2,242		 	100		
 	 	 	 	
Net (decrease) increase in cash, cash equivalents and restricted cash	(16,677	)	 	13,842		
Cash, cash equivalents and restricted cash at beginning of period	62,644		 	49,866		
Cash, cash equivalents and restricted cash at end of period	$	45,967		 	$	63,708		
 	 	 	 	
Non-cash investing and financing activity:	 	 	 	
Non-cash purchase consideration related to acquisition of Jiff	$	—		 	$	101,692		
 	 	 	 	
Reconciliation of cash, cash equivalents and restricted cash:	 	 	 	
Cash and cash equivalents	$	44,642		 	$	62,201		
Restricted cash	1,325		 	1,507		
Total cash, cash equivalents and restricted cash	$	45,967		 	$	63,708		
_______________________
(1) Prior-period information has been adjusted for the adoption of ASC 606 and ASU 2016-18, Statement of Cash Flows (“ASU 2016-18”) . See Note 2 – Accounting Standards and Significant Accounting Policies for a summary of adjustments.
See Notes to Condensed Consolidated Financial Statements .

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Note 1. Organization and Description of Business
Castlight Health, Inc. (“Castlight” or “the Company”) offers a comprehensive software-as-a-service platform that simplifies health benefits navigation for millions of employees. The Castlight platform matches employees to the best resources their employers make available to them, whether they are healthy, actively seeking medical care, or managing a condition, and motivates them to take the best steps for their health. Castlight helps employers generate more value from their benefits investments by helping to improve outcomes, lower health care costs, and increase benefits satisfaction. On April 3, 2017, the Company expanded into wellbeing through its acquisition of Jiff, Inc. (“Jiff”). Jiff's results of operations have been included in the Company’s Consolidated Statements of Operations beginning April 3, 2017. See Note 5– Business Combinations  for more information on the Jiff acquisition. The Company was incorporated in the State of Delaware in January 2008. The Company's principal executive offices are located in San Francisco, California.
Note 2. Accounting Standards and Significant Accounting Policies
Basis of Presentation and Principles of Consolidation
The accompanying unaudited condensed consolidated financial statements include Castlight and its wholly-owned subsidiaries. All intercompany balances and transactions have been eliminated in consolidation. The accompanying unaudited condensed consolidated financial statements have been prepared in accordance with U.S. generally accepted accounting principles (“GAAP”) and applicable rules and regulations of the Securities and Exchange Commission (“SEC”) regarding interim financial reporting. In the opinion of management, the information herein reflects all adjustments, consisting only of normal recurring adjustments except as otherwise noted, considered necessary for a fair statement of results of operations, financial position and cash flows. The results for the interim periods presented are not necessarily indicative of the results expected for any future period. The following information should be read in conjunction with the audited financial statements and notes thereto included in the Company’s Annual Report on Form 10-K for the year ended December 31, 2017 . 

Effective January 1, 2018, the Company adopted Accounting Standards Update (“ASU”) No. 2014-09, Revenue from Contracts with Customers (“ASC 606”) using the full retrospective method. Amounts and disclosures set forth in this Form 10-Q have been updated to comply with this new standard.

Certain prior period amounts reported in the condensed consolidated financial statements and notes have been reclassified to conform to current period presentation.
Use of Estimates

The preparation of condensed consolidated financial statements in conformity with GAAP requires the Company to make certain estimates, judgments and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities as of the date of the financial statements, as well as the reported amounts of revenue and expenses during the reporting period. These estimates include, but are not limited to the determination of:

• The fair value of assets acquired and liabilities assumed for business combination;
• The amortization period for deferred commissions and deferred professional services costs;
• Variable consideration included in the transaction price of the Company’s contracts with customers;
• The standalone selling price of the performance obligations in the Company’s contracts with customers; and
• Assumptions used in the valuation of certain equity awards.

Actual results could differ from those estimates, and such differences could be material to the Company’s consolidated financial position and results of operations.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Recently Adopted Accounting Pronouncements
Revenue Recognition
In May 2014 the Financial Accounting Standards Board (“FASB”) issued ASC 606. ASC 606 supersedes the revenue recognition requirements in ASC 605, Revenue Recognition , and requires the recognition of revenue when promised goods or services are transferred to customers in an amount that reflects the considerations to which the entity expects to be entitled to in exchange for those goods or services. ASC 606 also includes Subtopic 340-40, Other Assets and Deferred Costs - Contracts with Customers , which requires the deferral of incremental costs of obtaining and fulfilling a contract with a customer.
    
The key changes from adopting the new standard are:

•	Prior to the adoption of the new standard, the Company recognized revenue of the combined professional services and subscription deliverable over the contractual term of the subscription contract. For certain contracts, this included periods that were cancelable due to termination provisions. Under the new standard, the Company recognizes revenue for the combined professional services and subscription performance obligation over the non-cancelable term of the arrangement.  Additionally, prior to the adoption of the new standard, revenue related to variable fees was deferred until the fees became fixed or determinable.   Under the new standard, the Company estimates variable consideration at the most likely amount to which the Company expects to be entitled. The Company includes estimated amounts in the transaction price to the extent it is probable that a significant reversal of cumulative revenue recognized will not occur when the uncertainty associated with the variable consideration is resolved.	

•	Prior to the adoption of the new standard, the Company capitalized incremental and direct costs to obtain subscription contracts and amortized those costs over the non-cancelable portion of contracts. Under the new standard, the Company capitalizes all incremental costs to obtain subscription contracts and then amortizes those costs on a systematic basis that is consistent with the transfer to the customer of the goods or services to which those assets relate, which the Company has determined to be five years for initial subscription contracts or the contractual period for renewal subscription contracts.	
		
•	Prior to the adoption of the new standard, the Company expensed costs to fulfill subscription contracts when they were incurred. Under the new standard, the Company recognizes as assets certain costs incurred to fulfill subscription contracts. Additionally, under the new standard, these costs are amortized on a systematic basis over a period that is consistent with the transfer to the customer of the goods or services to which those assets relate, which the Company has determined to be five years.	
Select unaudited condensed consolidated balance sheet line items, which reflect the adoption of ASC 606 are as follows (in thousands): 

													
 	 	As of December 31, 2017	
 	 	Previously Reported	 	Adjustments	 	As Adjusted	
Assets	 	 	 	 	 	
 	Accounts receivable and other, net	$	20,761		 	$	1,172		 	$	21,933		
 	Deferred commissions (1)	10,583		 	16,929		 	27,512		
 	Deferred professional service costs	—		 	12,480		 	12,480		
Liabilities and stockholders' equity	 	 	 	 	 	
 	Deferred revenue	29,410		 	(3,425	)	 	25,985		
 	Deferred revenue, non-current	6,686		 	(2,229	)	 	4,457		
 	Accumulated deficit	(411,569	)	 	36,235		 	(375,334	)	
_______________________
		
(1)	As of December 31, 2017, Deferred commissions, current and non-current, were previously presented separately. The condensed consolidated balance sheet as of December 31, 2017 was reclassified to conform to the current period presentation.	

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Select unaudited condensed consolidated statement of operations line items, which reflect the adoption of ASC 606 are as follows (in thousands, except per share amounts):

																									
 	 	Three Months Ended June 30, 2017	 	Six Months Ended June 30, 2017	
 	 	Previously Reported	 	Adjustments	 	As Adjusted	 	Previously Reported	 	Adjustments	 	As Adjusted	
Revenue:	 	 	 	 	 	 	 	 	 	 	 	
 	Subscription	$	29,834		 	$	548		 	$	30,382		 	$	55,600		 	$	679		 	$	56,279		
 	Professional services and other	2,265		 	(15	)	 	2,250		 	4,243		 	(187	)	 	4,056		
Cost of revenue:	 	 	 	 	 	 	 	 	 	 	 	
 	Cost of professional services and other	4,793		 	(165	)	 	4,628		 	8,781		 	(344	)	 	8,437		
Operating expenses:	 	 	 	 	 	 	 	 	 	 	 	
 	Sales and marketing	16,575		 	(640	)	 	15,935		 	31,018		 	(937	)	 	30,081		
Operating loss	(18,935	)	 	1,338		 	(17,597	)	 	(33,937	)	 	1,773		 	(32,164	)	
Net loss	(13,717	)	 	1,338		 	(12,379	)	 	(28,526	)	 	1,773		 	(26,753	)	
Net loss per share, basic and diluted	(0.11	)	 	0.02		 	(0.09	)	 	(0.24	)	 	0.01		 	(0.23	)	
    
Statement of Cash Flows

In November 2016, the FASB issued ASU 2016-18, Statement of Cash Flows (“ASU 2016-18”) . The standard requires that a statement of cash flows explain the change during the period in the total of cash, cash equivalents, and amounts generally described as restricted cash or restricted cash equivalents. The standard became effective for the Company beginning January 1, 2018, and early adoption was permitted. The Company early adopted the standard in the fourth quarter of 2017 using the full retrospective method. As a result of adopting ASU 2016-18, the Company adjusted the condensed consolidated statement of cash flows from previously reported amounts. 

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Select unaudited condensed consolidated statement of cash flows line items, which reflect the adoption of ASC 606 and ASU 2016-18 are as follows (in thousands):

														
 	 	 	Six Months Ended June 30, 2017	
 	 	 	Previously Reported	 	Adjustments	 	As Adjusted	
Operating activities:	 	 	 	 	 	
Net loss	$	(28,526	)	 	$	1,773		(1)  	$	(26,753	)	
Adjustments to reconcile net loss to net cash used in operating activities:	 	 	 	 	 	
 	Stock-based compensation	12,541		 	(449	)	(1)  	12,092		
 	Amortization of deferred commissions	5,172		 	(883	)	(1)  	4,289		
 	Amortization of deferred professional costs	—		 	1,958		(1)  	1,958		
 	Changes in operating assets and liabilities:	 	 	 	 	 	
 	 	Deferred commissions	(3,398	)	 	(54	)	(1)  	(3,452	)	
 	 	Deferred professional service costs	—		 	(1,853	)	(1)  	(1,853	)	
 	Deferred revenue	7,202		 	(491	)	(1)  	6,711		
Net cash provided by investing activities	28,405		 	363		(2)  	28,768		
Net increase in cash, cash equivalents and restricted cash	13,479		 	363		(2)  	13,842		
Cash, cash equivalents and restricted cash at the beginning of period	48,722		 	1,144		 	49,866		
Cash, cash equivalents and restricted cash at the end of period	62,201		 	1,507		(2)  	63,708		
_______________________
(1) Adjusted to reflect the adoption of ASC 606.
(2) Adjusted to reflect the adoption of ASU 2016-18.

Financial Instruments

In January 2016, the FASB issued ASU No. 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities (“ASU 2016-01”), which amends various aspects of the recognition, measurement, presentation, and disclosure of financial instruments. The Company adopted ASU 2016-01 as of January 1, 2018 using the modified retrospective method for its marketable equity securities, which currently consist of money market mutual funds. The Company currently does not have any non-marketable equity securities. The adoption of ASU 2016-01 did not have a significant impact on the Company’s financial position or results of operations.

Summary of Significant Accounting Policies

Revenue Recognition

Revenues are derived primarily from contracts with customers for subscription services and professional services. Revenues are recognized when control of these services is transferred to the Company’s customers, in an amount that reflects the consideration the Company expects to be entitled to in exchange for those services. Revenues do not include sales taxes.
    
We determine revenue recognition through the following steps:

•	Identification of the contract, or contracts, with a customer;	
		
•	Identification of the performance obligations in the contract;	
		
•	Determination of the transaction price;	
		
•	Allocation of the transaction price to the performance obligations in the contract; and	
		
•	Recognition of revenue when, or as, the Company satisfies a performance obligation.	

Subscription Revenue. Subscription revenue recognition commences on the date that the Company’s subscription services are made available to the customer, which the Company considers to be the launch date, and subscription revenue is

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

generally recognized over the contract term. Subscription contracts are generally three years in length and certain contracts include termination provisions.

Some of the Company’s subscription contracts include performance incentives that are generally based on engagement. Additionally, some of the Company’s subscription contracts include audit provisions. The Company considers fees related to performance incentives and audit provisions to be variable consideration. The Company estimates variable consideration at the most likely amount to which it expects to be entitled. The Company includes estimated amounts in the transaction price to the extent it is probable that a significant reversal of cumulative revenue recognized will not occur when the uncertainty associated with the variable consideration is resolved. The Company’s estimates of variable consideration and determination of whether to include estimated amounts in the transaction price are based largely on an assessment of its anticipated performance as well as other information available to the Company. The Company reassesses its estimates related to variable consideration each reporting period and records adjustments when appropriate.

Professional Services and Other Revenue. Professional services and other revenue is primarily comprised of implementation services and communication services related to the Company's subscription service. Nearly all of the Company's professional services are sold on a fixed-fee basis.

The Company determined its implementation services are not capable of being distinct. Accordingly, the Company recognizes implementation services revenue in the same manner as the subscription service, beginning on the launch date. The Company determined its communication services are distinct and the associated revenue is recognized over time from the commencement of the communication services through the end of the contractual term.

Professional services and other revenue also includes revenue from products sold through the Company’s online marketplace and add-on subscription services made available from other ecosystem partners. These revenues are recognized on a net basis primarily because the Company acts as an agent in these contracts.

Contracts with Multiple Performance Obligations. Most of the Company’s contracts have multiple performance obligations consisting of subscription services and professional services, including implementation services and communication services. For arrangements with multiple performance obligations, the Company evaluates whether the individual performance obligations are distinct. If the performance obligations are distinct, revenue is recognized for the respective performance obligation separately. If one or more of the performance obligations are not distinct, the performance obligations that are not distinct are combined with the Company's subscription service, and revenue for the combined performance obligation is recognized over the term of the subscription service commencing on the launch date.

The Company has concluded that its subscription services and its communication services are distinct. Conversely, the Company has concluded that its implementation services are not distinct, primarily because these services are not capable of being distinct as the customer cannot benefit from the implementation services on their own. Accordingly, the Company considers the separate performance obligations in its multiple performance obligation contracts to be communication services and a combined performance obligation comprised of subscription services and implementation services.

The transaction price for arrangements with multiple performance obligations is allocated to the separate performance obligations based on their standalone selling price. The Company determines standalone selling prices based on its overall pricing objectives taking into consideration market conditions and other factors, including the value of the contracts, the subscription services sold, and customer demographics.

Contract Balances

The Company records a contract asset when revenue is recognized prior to invoicing. Contract assets are presented within accounts receivable and other in the accompanying condensed consolidated balance sheet. A contract liability represents deferred revenue.

Deferred revenue consists of professional services and cloud-based subscription services that have been billed in advance of revenue being recognized. The Company invoices its customers for its cloud-based subscription services based on the terms of the contract, which can be annual, quarterly or monthly installments. Deferred revenue that is anticipated to be

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

recognized during the succeeding 12-month period is recorded as current deferred revenue, and the remaining portion is recorded as non-current.

Accounts Receivable and Other

Accounts receivable are recorded when invoiced and at the invoiced amount, net of allowances for doubtful accounts, which are not significant for any period presented. When accounts receivable are recorded, the related revenue may not commence until a later date depending on the nature of the services invoiced.

Deferred Commissions

Deferred commissions are the incremental costs that are incurred to obtain contracts with customers and consist primarily of sales commissions paid to the Company's sales force and channel partners. The commissions for initial contracts are deferred and amortized on a straight-line basis over a period of benefit that the Company has determined typically to be five years. The Company determined the period of benefit by taking into consideration the expected life of its subscription contracts, the expected life of the technology underlying its subscription services and other factors. The commissions for renewal contracts are deferred and then amortized on a straight-line basis over the related contractual renewal period. The deferred commission amounts are recoverable through the Company’s future revenues. Amortization of deferred commissions is included in sales and marketing expense in the accompanying condensed consolidated statements of operations. All costs deferred are reviewed for impairment periodically.

Deferred Professional Service Costs
    
Deferred professional services costs are the direct costs incurred to fulfill subscription contracts that occur prior to the launch of the Company’s subscription services. Professional service costs, which primarily consist of employee related expenses attributable to launch activities, are deferred and then amortized on a straight-line basis over a period of benefit that the Company has determined typically to be five years for the same reasons as described in the deferred commissions disclosure above. Deferred professional service costs are recoverable through future revenues. Amortization of deferred professional service costs is included in cost of professional services and other revenue in the accompanying condensed consolidated statements of operations. All costs deferred are reviewed for impairment periodically.

Recently Issued Accounting Pronouncements
    
In February 2016, the FASB issued ASU 2016-02, Leases (“ASU 2016-02”). The guidance will require lessees to put all leases on their balance sheets, whether operating or financing, while continuing to recognize the expenses on their income statements in a manner similar to current practice. The guidance states that a lessee would recognize a lease liability for the obligation to make lease payments and a right-to-use asset for the right to use the underlying asset for the lease term. The guidance will be effective for the Company beginning January 1, 2019 and early adoption is permitted. The Company is evaluating the full effect the adoption will have on its financial condition, results of operations, and disclosures. The Company is evaluating the accounting, transition and disclosure requirements of the standard and cannot currently estimate the impact of adoption on its consolidated financial statements.     

In February 2018, the FASB issued ASU 2018-02, Income Statement – Reporting Comprehensive Income: Reclassification of Certain Tax Effects from Accumulated Other Comprehensive Income (“ASU 2018-02”). The provisions in ASU 2018-02 allow for a reclassification from accumulated other comprehensive income to retained earnings to eliminate the stranded tax effects resulting from the change in federal corporate income tax rate in the Tax Cuts and Jobs Act enacted in December 2017. The Company is required to adopt ASU 2018-02 on January 1, 2019. Early adoption is permitted, including adoption in any interim period for which financial statements have not yet been issued. The adoption of ASU 2018-02 is not expected to have a significant impact on the Company’s financial position or results of operations.

In June 2016, the FASB issued ASU No. 2016-13, Financial Instruments-Credit Losses (“ASU 2016-13”). The standard changes how entities will measure credit losses for most financial assets and certain other instruments that are not measured at fair value through net income. The Company will recognize an allowance for credit losses on available-for-sale securities rather than deductions in amortized cost. The standard is effective for fiscal years and interim periods beginning after

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

December 15, 2019. Early adoption is permitted for all periods beginning after December 15, 2018. The adoption of this standard is not expected to have a significant impact on the Company’s financial statements.

Note 3. Revenue, Deferred Revenue, Contract Balances and Performance Obligations
    
The Company sells to customers based in the United States.

Deferred revenue as of June 30, 2018 and December 31, 2017 was $29.2 million and $30.4 million , respectively. Contract assets as of June 30, 2018 and December 31, 2017 were $1.8 million and $1.2 million , respectively.

$16.5 million and $12.4 million of revenue was recognized during the three months ended June 30, 2018 and 2017 , respectively, that was included in the deferred revenue balances at the beginning of the respective periods. $22.6 million and $17.1 million of revenue was recognized during the six months ended June 30, 2018 and 2017 , respectively, that was included in the deferred revenue balances at the beginning of the respective periods.

The Company recorded unfavorable cumulative catch-up adjustments to revenue arising from changes in estimates of transaction price of $0.8 million and $0.6 million during the three and six months ended June 30, 2018 , respectively.

The aggregate balance of remaining performance obligations from non-cancelable contracts with customers as of June 30, 2018 was $143.7 million . The Company expects to recognize approximately 70% of this balance over the next 12 months, with the remaining balance recognized thereafter. Remaining performance obligations are defined as deferred revenue and amounts yet to billed for the non-cancelable portion of contracts.
Note 4. Deferred Costs

Changes in the balance of total deferred commissions and total deferred professional service costs during the six months ended June 30, 2018 are as follows (in thousands):

																
 	As of December 31, 2017 (1)	 	 	 	Expense recognized	 	As of June 30, 2018	
 		 	Additions	 				
Deferred commissions	$	27,512		 	$	2,979		 	$	(5,800	)	 	$	24,691		
Deferred professional service costs	12,480		 	1,472		 	(2,097	)	 	11,855		
Total deferred commissions and professional service costs	$	39,992		 	$	4,451		 	$	(7,897	)	 	$	36,546		
______________________
		
(1)	Prior-period information has been adjusted for the adoption of ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies for a summary of adjustments.	

    These costs are reviewed for impairment periodically, and no material impairment charges were recorded for the three and six months ended June 30, 2018 .
    
Note 5. Business Combinations
    
On April 3, 2017, the Company completed its acquisition of Jiff, Inc. Prior to its acquisition, Jiff provided an enterprise health benefits platform that served as a central hub for employee wellbeing and employee benefit programs. The acquisition enabled the Company to offer a wellbeing platform, healthcare decision support and a benefits hub in one comprehensive package. The Company acquired Jiff for approximately 27,000,000 in shares and options.

At the closing of the transaction on April 3, 2017, Venrock, a holder of more than 5% of the Company’s capital stock, acquired a total of 3,965,979 shares of the Company’s Class B common stock in exchange for its shares of Jiff capital stock. Bryan Roberts, who is the chairman of the Company’s board of directors is also a partner at Venrock. Accordingly, the business combination was considered a related party transaction.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

The Company’s board appointed a special committee, comprised solely of disinterested directors, to which it delegated the full and exclusive power, authority and discretion to evaluate, assess, and approve the Jiff transaction on its
behalf, including retaining a financial advisor for an opinion on the fairness of the financial conditions of the transaction. The transaction was approved solely by the special committee, which concluded that the transaction terms were fair to the Company and that the transaction was in the best interests of the Company and its stockholders.

As part of the merger, all options to purchase Jiff common stock held by Jiff employees who became employees of the combined company were converted into options to purchase the Company’s Class B common stock. Additionally, certain stockholders and option holders were to receive an aggregate of  1,000,000 shares of the Company’s Class B common stock or options to purchase the Company’s Class B common stock if the Jiff business achieved at least  $25 million  in revenue in 2017, and an aggregate of  3,000,000 shares of Class B common stock or options to purchase the Company’s Class B common stock if the Jiff business achieved at least  $25 million  in net new bookings during 2017 (“the milestones”). As of December 31, 2017, the Company evaluated and determined that both milestones were not met.

The following table summarizes the components of the purchase consideration transferred based on the closing price of the Company’s stock as of the acquisition date (in thousands):

					
 	 	Fair value	
Fair value of Company Class B common stock (25,054,049 shares @ $3.65 per share)	 	$	91,447		
Fair value of contingent consideration	 	671		
Fair value of assumed Jiff options attributable to pre-combination services	 	9,574		
Transaction costs paid on behalf of Jiff	 	4,498		
Estimated purchase price consideration	 	$	106,190		
    
For the Jiff options assumed as part of the acquisition, the Company applied the ratio of pre-combination service provided, on a grant-by-grant basis, to the total service period and applied this ratio to the acquisition date fair value of the Jiff awards.

The Company determined that the contingent consideration shares associated with the milestones are one unit of account, and classified the contingent consideration as a liability as the arrangement can be settled in a variable number of shares and is not considered fixed-for-fixed. The Company determined that the fair value of the contingent consideration liability was $0.7 million at the date of the acquisition. The fair value was estimated by applying the Monte Carlo simulation model, based on the probability of completing the milestones and the changes in the fair value of the Company’s common stock. As of December 31, 2017, the Company determined there would be no related payment because the milestones were not met.

The final allocation of purchase consideration to assets acquired and liabilities assumed is reflected below. There were no changes to amounts previously recorded as assets or liabilities that resulted in a corresponding adjustment to goodwill.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

The fair values of the assets acquired and liabilities assumed by major class in the acquisition of Jiff were recognized as follows (in thousands):

				
Cash	$	2,234		
Current assets	5,159		
Other assets	1,971		
Acquired intangible assets	23,900		
Goodwill	91,785		
    Total assets acquired	125,049		
Deferred revenue	(1,857	)	
Other current liabilities	(6,192	)	
Debt	(5,578	)	
Non-current liabilities	(5,232	)	
Total net assets acquired	$	106,190		

The fair values assigned to tangible assets acquired, liabilities assumed and identifiable intangible assets are based on management’s estimates and assumptions. The excess of purchase consideration over the fair value of net tangible and identifiable intangible assets acquired was recorded as goodwill. The goodwill balance is primarily attributed to the cross-selling opportunities, cost synergies, and a knowledgeable and experienced workforce which play an important role in the integration of the acquired customers and technology. The goodwill balance is not deductible for U.S. income tax purposes.

The following table sets forth the fair value components of identifiable acquired intangible assets (dollars in thousands): 

									
 	 	Fair Value	 	Useful Life	
Customer relationships	 	$	10,900		 	10	
Developed technology	 	10,600		 	5	
Backlog	 	1,500		 	3	
Other acquired intangible assets	 	900		 	1	-	3	
Total identifiable intangible assets	 	$	23,900		 	 	 	 	
    
Customer relationships represent the fair value of projected cash flows that will be derived from the sale of products to Jiff's existing customers based on existing, in-process, and future versions of the underlying technology. Developed technology represents Jiff’s benefits platform. The Company used the relief from royalty method to value the developed technology. To determine the net cash flow that a market participant would expect to realize from licensing the Company's technology, the Company estimated a net royalty rate, which excludes any expenses that would be incurred to maintain the current functionality of the technology.

The Company has included the financial results of Jiff in the Company’s condensed consolidated statements of operations from the date of acquisition.

The unaudited pro forma financial information in the table below summarizes the combined results of operations for the Company and Jiff as if the companies were combined as of the beginning of 2016 (the beginning of the comparable prior reporting period in the year of acquisition). The unaudited pro forma condensed combined financial information is presented for informational purposes only.

The historical consolidated financial statements have been adjusted in the pro forma combined financial statements to give effect to pro forma events that are directly attributable to the business combination and factually supportable. The unaudited pro forma financial information presented includes the business combination accounting effects resulting from the acquisition, including amortization charges from acquired intangible assets, stock-based compensation, and acquisition-related costs. In addition, the pro forma combined financial statements give effect to the adoption of ASC 606 in 2018.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

The following table presents the unaudited pro forma condensed combined financial information for the periods presented, except for the financial information presented for the three and six months ended June 30, 2018 which is presented on an as-reported basis (in thousands):

																
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	2017	 	2018	 	2017	
Total revenue	$	37,784		 	$	32,598		 	$	74,263		 	$	63,943		
Net loss	(13,958	)	 	(15,490	)	 	(28,402	)	 	(33,957	)	
    
Note 6. Goodwill and Intangible Assets

Goodwill

Currently, all of the Company’s goodwill relates to the acquisition of Jiff. The excess of purchase consideration over the fair value of net tangible and identifiable intangible assets acquired was recorded as goodwill. There were no changes to goodwill for the three and six months ended June 30, 2018 .

Intangible assets, net
    
The following tables set forth the fair value components of identifiable acquired intangible assets (dollars in thousands):

																
 	June 30, 2018	
 	Useful Life	 	Gross	 	Accumulated Amortization	 	Net	
Customer relationships	10	 	$	10,900		 	$	(1,363	)	 	$	9,537		
Developed technology	5	 	10,600		 	(2,650	)	 	7,950		
Backlog	3	 	1,500		 	(960	)	 	540		
Other acquired intangible assets	1	-	3	 	900		 	(783	)	 	117		
Total identifiable intangible assets	 	 	 	 	$	23,900		 	$	(5,756	)	 	$	18,144		

	
																
 	December 31, 2017	
	Useful Life	 	Gross		Accumulated Amortization		Net	
Customer relationships	10	 	$	10,900			$	(818	)		$	10,082		
Developed technology	5	 	10,600			(1,590	)		9,010		
Backlog	3	 	1,500			(664	)		836		
Other acquired intangible assets	1	-	3	 	900			(575	)		325		
Total identifiable intangible assets				 	$	23,900			$	(3,647	)		$	20,253		

Amortization expense from acquired intangible assets for the three months ended June 30, 2018 and 2017 was $1.0 million and $1.2 million , respectively. Amortization expense from acquired intangible assets for the six months ended June 30, 2018 and 2017 was $2.1 million and $1.2 million , respectively. Amortization expense is included in cost of subscription, and general and administrative, and sales and marketing expenses.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Estimated amortization expense for acquired intangible assets for the following five years and thereafter is as follows (in thousands):

				
Remainder of 2018	$	1,934		
2019	3,505		
2020	3,242		
2021	3,210		
2022	1,620		
Thereafter	4,633		
Total estimated amortization expense	$	18,144		

Note 7. Marketable Securities

All of the Company’s cash equivalents and marketable securities are classified as “available-for-sale” securities. These securities are reported at fair value, with the related unrealized gains and losses included in accumulated other comprehensive income, a component of stockholders’ equity , except for money market mutual funds, where gains and losses are included in the results of operation.

As of June 30, 2018 and December 31, 2017 , respectively, marketable securities consisted of the following (in thousands):

																
 	As of June 30, 2018	
 	Amortized
Cost	 	Unrealized
Gains	 	Unrealized
Losses	 	Fair Value	
U.S. treasury securities	$	23,610		 	$	—		 	$	(8	)	 	$	23,602		
U.S. agency obligations	14,972		 	—		 	(1	)	 	14,971		
Money market mutual funds	6,287		 	—		 	—		 	6,287		
 	44,869		 	—		 	(9	)	 	44,860		
Included in cash and cash equivalents	15,027		 	—		 	—		 	15,027		
Included in marketable securities	$	29,842		 	$	—		 	$	(9	)	 	$	29,833		

	
																
 	December 31, 2017	
 	Amortized
Cost	 	Unrealized
Gains	 	Unrealized
Losses	 	Fair Value	
U.S. treasury securities	$	31,047		 	$	—		 	$	(22	)	 	$	31,025		
U.S. agency obligations	19,366		 	—		 	—		 	19,366		
Money market mutual funds	6,115		 	—		 	—		 	6,115		
 	56,528		 	—		 	(22	)	 	56,506		
Included in cash and cash equivalents	24,481		 	—		 	—		 	24,481		
Included in marketable securities	$	32,047		 	$	—		 	$	(22	)	 	$	32,025		

Note 8. Fair Value Measurements
The Company measures its financial assets and liabilities at fair value at each reporting period using a fair value hierarchy that requires that the Company maximize the use of observable inputs and minimize the use of unobservable inputs when measuring fair value. A financial instrument’s classification within the fair value hierarchy is based upon the lowest level of input that is significant to the fair value measurement. Three levels of inputs may be used to measure fair value:

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Level 1—Observable inputs that reflect quoted prices (unadjusted) for identical assets or liabilities in active markets.
Level 2—Include other inputs that are directly or indirectly observable in the marketplace.
Level 3—Unobservable inputs that are supported by little or no market activity.
The fair value of marketable securities included in the Level 2 category is based on observable inputs, such as quoted prices for similar assets at the measurement date; quoted prices in markets that are not active; or other inputs that are observable, either directly or indirectly. These values were obtained from a third-party pricing service and were evaluated using pricing models that vary by asset class and may incorporate available trade, bid and other market information and price quotes from well-established third party pricing vendors and broker-dealers.
There have been no changes in valuation techniques in the periods presented. There were no significant transfers between fair value measurement levels as of June 30, 2018 and December 31, 2017 . As of June 30, 2018 and December 31, 2017 , there were no securities within Level 3 of the fair value hierarchy.
The following tables present information about the Company’s assets and liabilities that are measured at fair value on a recurring basis using the above input categories (in thousands): 

												
 	As of June 30, 2018	
 	Level 1	 	Level 2	 	Total	
Cash equivalents:	 	 	 	 	 	
U.S. agency obligations	$	—		 	$	7,740		 	$	7,740		
Money market mutual funds	6,287		 	—		 	6,287		
U.S. treasury securities	—		 	1,000		 	1,000		
Marketable securities:	 	 	 	 	 	
U.S. treasury securities	—		 	22,602		 	22,602		
U.S. agency obligations	—		 	7,231		 	7,231		
 	$	6,287		 	$	38,573		 	$	44,860		

	
												
 	As of December 31, 2017	
 	Level 1	 	Level 2	 	Total	
Cash equivalents:	 	 	 	 	 	
U.S. agency obligations	$	—		 	$	18,366		 	$	18,366		
Money market mutual funds	6,115		 	—		 	6,115		
Marketable securities:	 	 	 	 	 	
U.S. treasury securities	—		 	31,025		 	31,025		
U.S. agency obligations	—		 	1,000		 	1,000		
 	$	6,115		 	$	50,391		 	$	56,506		
Gross unrealized gains and losses for cash equivalents and marketable securities as of June 30, 2018 and December 31, 2017 were not material. The Company does not believe the unrealized losses represent other-than-temporary impairments based on the Company’s evaluation of available evidence as of June 30, 2018 and December 31, 2017 .
There were no realized gains or losses during the three and six months ended June 30, 2018 . All of the Company’s marketable securities as of June 30, 2018 and December 31, 2017 mature within one year . Marketable securities on the balance sheets consist of securities with original or remaining maturities at the time of purchase of greater than three months, and the remainder of the securities is reflected in cash and cash equivalents.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Note 9. Property and Equipment
Property and equipment consisted of the following (in thousands):

								
 	As of	
 	June 30, 2018	 	December 31, 2017	
Leasehold improvements	$	3,393		 	$	2,915		
Computer equipment	6,799		 	6,165		
Software	1,134		 	1,149		
Internal-use software	2,925		 	2,925		
Furniture and equipment	1,154		 	1,293		
Total	15,405		 	14,447		
Accumulated depreciation	(10,158	)	 	(9,184	)	
Property and equipment, net	$	5,247		 	$	5,263		
Depreciation and amortization expense for the three months ended June 30, 2018 and 2017 was $0.8 million and $0.8 million , respectively . Depreciation and amortization expense for the six months ended June 30, 2018 and 2017 was $1.5 million and $1.5 million , respectively . Depreciation and amortization are recorded on a straight-line basis.
Note 10. Debt

Term Loan

In connection with the Company’s acquisition of Jiff, on April 3, 2017, the Company, Jiff and Silicon Valley Bank (the “Bank”) agreed to refinance the existing term loan facility owed by Jiff to the Bank (the “Loan Agreement”) for approximately  $5.6 million (the “Term Loan”). The Term Loan requires interest-only payments for the period May 2017 through September 2018, followed by 36 monthly payments of principal and interest. Obligations under the Term Loan accrue interest at a floating per annum rate equal to the greater of (A) the prime rate as published in the money rates section of The Wall Street Journal ( “Prime Rate”) minus 1% or (B) 0% . Interest on the Term Loan is payable monthly. The maturity date of the Term Loan is September 1, 2021.

In addition to principal and interest payments, the Company is also required to pay $0.5 million as final payment on the earlier of maturity, termination or prepayment of the Term Loan. The Company accrues for the final payment over the life of the Term Loan using the effective interest method.
    
The future maturities of the Term Loan by year as of  June 30, 2018 are as follows (in thousands):

				
Remainder of 2018	$	620		
2019	1,859		
2020	1,859		
2021 (1)	1,240		
Total future maturities of debt (2)	$	5,578		
_______________________
(1) Excludes the $0.5 million required to be paid as final payment on the earlier of maturity, termination or prepayment of the Term Loan.
(2) Includes $1.4 million classified as debt, current (within accrued expenses and other current liabilities) and $4.2 million classified as debt, non-current on the condensed consolidated balance sheet as of June 30, 2018 .

Revolving Line of Credit     

The Loan Agreement also provides for an up to $25 million  revolving credit facility (the “Revolving Line”). The Company may request borrowings under the Revolving Line prior to April 3, 2019, on which date the Revolving Line terminates. As of June 30, 2018 , no borrowings have been made under the Revolving Line.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

In relation to the Loan Agreement, the Company is subject to certain financial and reporting covenants. As of June 30, 2018 , none of the financial covenants, which require the Company to maintain a certain minimum liquidity ratio, are applicable. The Company was in compliance with all reporting covenants in the Loan Agreement related to the outstanding principal balance as of June 30, 2018 .     

Note 11. Related Party Transactions and Variable Interest Entity

In 2015, the Company made a preferred stock investment of  $4.1 million  and entered into a strategic alliance with Lyra Health, Inc. ("Lyra"), a related party at the time of the investment. During the fourth quarter of 2017, the Company sold its investment in Lyra to a group of buyers that included related parties for a total selling price of $5.5 million .

Lyra was considered a related party to the Company because two of the Company’s directors, Dr. Roberts and Mr. Ebersman, serve on the Lyra board of directors and Mr. Ebersman is Lyra’s chief executive officer. Prior to the sale of the investment in Lyra, the Company determined that Lyra is a variable interest entity and that it was not required to consolidate the operations of Lyra.

Because Lyra was a related party and potential buyers were also related parties, the Company formed an independent committee of the Company's board of directors (the "Independent Committee"), comprised solely of disinterested directors, to approve the sale. The Company also engaged an independent third-party valuation expert to assist in determining the fair value of the Company's investment in Lyra. Based in part on the valuation performed, the Company negotiated a selling price of  $5.5 million , which the Independent Committee approved after concluding that the transaction terms were fair to the Company. The sale resulted in a pre-tax gain of  $1.4 million  which was recorded in other income, net within the consolidated statements of operations included in the Company’s Annual Report on Form 10-K for the year ended December 31, 2017 . 

Note 12. Commitments and Contingencies
Legal Matters

From time to time, the Company may become subject to other legal proceedings, claims or litigation arising in the ordinary course of business. In addition, the Company may receive letters alleging infringement of patents or other intellectual property rights. If an unfavorable outcome were to occur in litigation, the impact could be material to the Company’s business, financial condition, cash flow or results of operations, depending on the specific circumstances of the outcome. The Company accrues for loss contingencies when it is both probable that it will incur the loss and when it can reasonably estimate the amount of the loss or range of loss.
    
Leases and Contractual Obligations

The Company’s principal commitments primarily consist of obligations under leases for office space and co-location facilities for data center capacity. The Company’s existing lease agreements provide it with the option to renew and generally provide for rental payments on a graduated basis. The Company’s future operating lease obligations would change if it entered into additional operating lease agreements as the Company expands its operations and if it exercised these options.

In March 2018, the Company subleased a portion of its engineering office located in Mountain View, California reducing its total rent obligation by $2.4 million and recognizing a one-time sublease loss of $0.9 million in research and development expense in the accompanying condensed consolidated statement of operations.

In June 2018, the Company recognized a lease exit charge of approximately $0.8 million related to the remaining engineering office space in Mountain View, California that the Company will no longer utilize . This charge is recorded in research and development expense in the accompanying condensed consolidated statement of operations.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

Note 13. Stock Compensation
Restricted Stock Units

A summary of restricted stock unit activity for the six months ended June 30, 2018 is as follows:

							
 	Number of
Shares
Outstanding	 	Weighted-
Average
Grant Date Fair Value	
Balance as of December 31, 2017	9,333,896		 	$	4.03		
Restricted Stock Units granted (1)	4,797,974		 	$	3.69		
Restricted Stock Units vested	(1,662,426	)	 	$	4.32		
Restricted Stock Units forfeited and canceled (2)	(1,737,125	)	 	$	3.65		
Balance as of June 30, 2018	10,732,319		 	$	3.66		
_______________________
(1) Includes 0.7 million performance stock units (“PSUs”) that were granted during the six months ended June 30, 2018 .
(2) Includes PSUs that were granted in the prior year, which were canceled because performance targets were not achieved.
As of June 30, 2018 , there was a total of $36.5 million in unrecognized compensation cost related to restricted stock units and performance stock units, which is expected to be recognized over a weighted-average period of approximately 2.68 years.

During 2018 , the Company awarded 0.7 million PSUs to certain employees. The number of shares that will eventually vest depends on achievement of performance targets for 2018 , as determined by the compensation committee of the Company's board of directors, and may range from 0 % to 150% of the targeted award amount. Once the performance is determined and a targeted award amount is fixed, the target number of PSUs, if any, will vest in eight quarterly installments , subject to recipients' continued service, beginning on February 16, 2019 . The compensation expense associated with the PSUs is recognized using the accelerated method. For the three and six months ended June 30, 2018 , the Company recognized compensation expense of approximately  $0.3 million and $0.5 million , respectively, related to performance awards.
Stock Options
A summary of stock option activity for the six months ended June 30, 2018 is as follows:  

											
 	Options
Outstanding	 	Weighted-
Average
Exercise
Price	 	Aggregate
Intrinsic
Value	
Balance as of December 31, 2017	10,335,178		 	$	2.83		 	$	19,253		
Stock option grants	134,000		 	$	3.69		 	 	
Stock options exercised	(1,527,309	)	 	$	1.47		 	 	
Stock options forfeited and canceled	(581,748	)	 	$	12.93		 	 	
Balance as of June 30, 2018	8,360,121		 	$	2.39		 	$	19,499		
The total grant-date fair value of stock options granted during the six months ended June 30, 2018 and 2017 was $0.3 million and $0.8 million , respectively.

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CASTLIGHT HEALTH, INC.
NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
(unaudited)

The fair value of each option grant was estimated on the date of grant using the Black-Scholes option-valuation model with the following assumptions and fair value per share:

								
 	Six Months Ended June 30,	
 	2018	 	2017	
Volatility	57%	 	61%	
Expected life (in years)	6.06	 	6.02	
Risk-free interest rate	2.72	%	-	2.74	%	 	2.03%	
Dividend yield	—%	 	—%	
As of June 30, 2018 , the Company had $2.4 million in unrecognized compensation cost related to non-vested stock options, which is expected to be recognized over a weighted-average period of approximately 2.36 years.     
Note 14. Stockholders’ Equity
Common Stock
As of June 30, 2018 , the Company had 51,923,213 shares of Class A common stock and 85,805,797 shares of Class B common stock outstanding.
Transactions with SAP Technologies, Inc.

In May 2016, the Company entered into a Securities Purchase Agreement (the “Securities Purchase Agreement”) with SAP Technologies, Inc. (“SAP”) pursuant to which it sold and issued to SAP  4.7 million  shares of its Class B Common Stock and a warrant (the “Warrant”), which gave SAP rights to purchase up to  1.9 million  shares of the Company's Class B Common Stock for an exercise price of  $4.91 , subject to certain conditions. The net proceeds from this transaction were  $17.8 million , net of issuance costs, and were used for working capital and other general corporate purposes.
The Warrant was set to expire four years from the date the Company enters into agreements with SAP related to the distribution and the reselling of the Company’s solutions (the “Alliance Agreement”) within a prescribed period. During the second quarter of 2017, the Company and SAP modified the Warrant to extend the time period allowed to execute the Alliance Agreement from May 17, 2017 to November 17, 2017. However, the Alliance Agreement was not executed prior to that date and as a result, the Warrant expired.
The shares and Warrant were considered freestanding instruments and were classified within stockholders’ equity. Initially, upon execution of the Securities Purchase Agreement, the Company preliminarily allocated the net proceeds to the shares, Warrant and a customer prepayment liability classified within accrued expenses and other current liabilities. However, as a result of the Warrant modification during the second quarter of 2017, the Company adjusted its allocation of the net proceeds, changing the classification of the customer prepayment liability to other assets. During the fourth quarter of 2017, the Company released the associated other asset and recorded a  $1.1 million  non-cash charge in other income, net in the consolidated statement of operations included in the Company’s Annual Report on Form 10-K for the year ended December 31, 2017.

Note 15. Income Taxes
    
The effective tax rate for the three and six months ended June 30, 2018 was zero percent. The effective tax rate for the three and six months ended June 30, 2017 was (29.6)% and (16.3)% , respectively. A s a result of the acquisition of Jiff in April 2017, the Company recorded a tax benefit of $5.2 million as a discrete item in the second quarter of 2017. This tax benefit is a result of the partial release of its existing valuation allowance since the acquired deferred tax liabilities from Jiff will provide a source of income for the Company to realize a portion of its deferred tax assets, for which a valuation allowance is no longer needed. As of June 30, 2018 , all unrecognized tax benefits are subject to a full valuation allowance and, if recognized, will not affect the effective tax rate.

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The Tax Cuts and Jobs Act enacted on December 22, 2017 resulted in substantial changes including reducing the US federal corporate income tax rate from 35 percent to 21 percent and requiring companies to pay a one-time transition tax on earnings of certain foreign subsidiaries that were previously tax deferred. The Act creates new taxes starting in 2018 on certain foreign sourced earnings. The Company applied the guidance in SAB 118 and at December 31, 2017 recorded provisional estimates to re-measure deferred taxes and liabilities using the new 21 percent rate which resulted in a net decrease of  $54.6 million , with a corresponding offsetting change in valuation allowance of  $54.6 million .

During the three and six months ended June 30, 2018 , the Company has not recorded any measurement period adjustments to the provisional estimates recorded at December 31, 2017.
Note 16. Net Loss per Share
Basic net loss per share is computed by dividing the net loss by the weighted-average number of shares of common stock outstanding during the period. Diluted net loss per share is computed by giving effect to all potential shares of common stock, including Preferred Stock and outstanding stock options and warrants, to the extent dilutive. Basic and diluted net loss per share was the same for each period presented as the inclusion of all potential shares of common stock outstanding would have been anti-dilutive .
Net loss is allocated based on the contractual participation rights of the Class A and Class B common stock as if the earnings for the year have been distributed. As the liquidation and dividend rights are identical, the net loss is allocated on a proportionate basis .
    
The following table presents the calculation of basic and diluted net loss per share for the Company’s common stock (in thousands, except per share data): 

																																
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	2017 (1)	 	2018	 	2017 (1)	
 	Class A	 	Class B	 	Class A	 	Class B	 	Class A	 	Class B	 	Class A	 	Class B	
Net loss	$	(5,315	)	 	$	(8,643	)	 	$	(5,123	)	 	$	(7,256	)	 	$	(10,956	)	 	$	(17,446	)	 	$	(12,298	)	 	$	(14,455	)	
Weighted-average shares used to compute basic and diluted net loss per share	52,043		 	84,639		 	54,018		 	76,519		 	52,401		 	83,442		 	54,153		 	63,654		
Basic and diluted net loss per share	$	(0.10	)	 	$	(0.10	)	 	$	(0.09	)	 	$	(0.09	)	 	$	(0.21	)	 	$	(0.21	)	 	$	(0.23	)	 	$	(0.23	)	
_______________________
		
(1)	Prior-period information has been adjusted for the adoption of ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies for a summary of adjustments.	
The following securities were excluded from the calculation of diluted net loss per share for common stock because their effect would have been anti-dilutive for the periods presented (in thousands):

												
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	2017	 	2018	 	2017	
Stock options and restricted stock units	19,092		 	22,239		 	19,092		 	22,239		
Warrants (1)	115		 	2,020		 	115		 	2,020		
Contingent issuable shares related to Jiff (2)	—		 	3,284		 	—		 	3,284		
Total	19,207		 	27,543		 	19,207		 	27,543		
_______________________
(1)     2017 includes 1.9 million warrants issued to SAP that expired during the fourth quarter of 2017, as described in Note 14 – Stockholders’ Equity .
		
(2)	As of December 31, 2017, the Company determined there would be no related payment because the milestones were not met. See Note 5 – Business Combinations for additional information.	

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Note 17. Subsequent Events

On August 1, 2018, the Company’s Board of Directors committed to a program to reduce its workforce in order to reduce expenses, align its operations with evolving business needs and improve efficiencies. This was in part due to the unexpected churn of a large customer. Under this program, the Company intends to reduce total expenses by 10% - 15% including a reduction of its workforce. The actions associated with this program are expected to be largely completed by September 30, 2018. The Company is unable at this time to make a good faith estimate of the major costs associated with this program, including charges it will incur or related cash expenditures.

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ITEM 2. MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

FORWARD-LOOKING STATEMENTS
This Quarterly Report on Form 10-Q contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, which are subject to the “safe harbor” created by those sections. Forward-looking statements are based on our management’s beliefs and assumptions and on information currently available to our management. In some cases, you can identify forward-looking statements by terms such as “may,” “will,” “should,” “could,” “goal,” “would,” “expect,” “plan,” “anticipate,” “believe,” “intend,” “estimate,” “project,” “predict,” “potential” and similar expressions intended to identify forward-looking statements. These statements involve known and unknown risks, uncertainties and other factors, which may cause our actual results, performance, time frames or achievements to be materially different from any future results, performance, time frames or achievements expressed or implied by the forward-looking statements. We discuss many of these risks, uncertainties and other factors in this Quarterly Report on Form 10-Q in greater detail under the section titled “Risk Factors” set forth in Part II, Item 1A in this Quarterly Report on Form 10-Q. Given these risks, uncertainties and other factors, you should not place undue reliance on these forward-looking statements. Also, these forward-looking statements represent our estimates and assumptions only as of the date of this filing. You should read this Quarterly Report on Form 10-Q completely and with the understanding that our actual future results may be materially different from what we expect. We hereby qualify our forward-looking statements by these cautionary statements.
    
Although we believe that the expectations reflected in the forward-looking statements are reasonable, we cannot guarantee future results, levels of activity, performance or achievements. We are under no duty to update any of these forward-looking statements after the date of this Quarterly Report on Form 10-Q or to conform these statements to actual results or revised expectations.
 
All references to “Castlight,” “Castlight Health,” “we,” “us,” “our” or the “Company” mean Castlight Health, Inc. and its subsidiaries, except where it is made clear that the term means only the parent company.

Overview
    
Castlight Health, Inc. (“Castlight”, “the Company” or "we") offers a comprehensive software-as-a-service (“SaaS”) platform that simplifies health benefits navigation for millions of employees. Our platform matches employees to the best resources their employers make available to them - whether they are healthy, actively seeking medical care, or managing a condition - and motivates them to take the best steps for their health. Castlight helps employers generate more value from their benefits investments by helping to improve outcomes, lower health care costs, and increase benefits satisfaction.

Castlight’s platform solution supports strong employee engagement and satisfaction through two foundational components: an ecosystem of deep integrations across an employer’s various health and wellbeing partners; and a predictive analytics “engine” that uses claims, demographic and user data and machine learning to personalize clinical options, benefit programs, wellbeing incentives, communications, and educational content, based on each employee’s specific health and wellbeing needs.

This unique combination of data integrations and personalization puts Castlight in a position to deliver value to employees and their employers. For employees, our platform improves their healthcare experience, with a highly-engaging, seamless mobile application and web experience, which are coupled with multi-channel communications. In addition, the platform’s rewards feature is designed to incentivize individuals to participate in health programs, optimize their care utilization, and improve their daily habits. For employers, Castlight provides a simplified, cost-effective, and flexible way to manage health benefits: allowing them to procure, deploy, manage, and measure a vast majority of their healthcare and wellbeing program vendors through a single platform.

Castlight was incorporated in the State of Delaware in January 2008. Its first generation care guidance solutions addressed the needs of employees actively seeking care or managing a chronic condition and serve as the foundation of our current care guidance offering. In 2015, we launched Castlight Action, our data-driven personalization benefits content and recommendations platform, which has been integrated into all of our products and rebranded as Castlight Genius. In April

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2017, we acquired Jiff, Inc. Jiff provides an enterprise health benefits platform that serves as a central hub for employee wellbeing and employee benefit programs, and is the foundation for our wellbeing offering.
Key Factors Affecting Our Performance

Sales of New and Additional Products.  Our revenue growth rate and long-term profitability are affected by our ability to sell new and additional products to new and existing customers, directly and through our channel partners. Additionally, we believe that there is a significant opportunity to sell subscriptions to add-on products as our customers become more familiar with our offering and seek to address additional needs.

Renewals of Customer Contracts.  We believe that our ability to retain our customers and expand their subscription revenue growth over time will be an indicator of the stability of our revenue base and the long-term value of our customer relationships.

Channel Partnerships.  We have relationships with channel partners, including Anthem, which complement our direct sales capabilities. These relationships allow deeper penetration into our market and enable us to promote our health benefits platform and products to create customer cross-selling opportunities.

Ecosystem Partnerships. We have relationships with digital health partners that integrate with our platform to provide a more streamlined experience for our customers and users. We also have over 1,000 third-party benefit solutions integrated with our products to enable effortless access to these programs to our users. We believe these partnerships enable a single user experience that is essential to drive engagement and increase user satisfaction.

Implementation Timelines.  Our ability to convert backlog into revenue and improve our gross margin depends on how quickly we complete customer implementations. Our implementation timelines vary from customer to customer based on the source and condition of the data we receive from third parties, the configurations that we agree to provide and the size of the customer. Our implementation timelines for our products are typically three to 12 months after entering into an agreement with a customer.

Professional Services Model.  We believe our professional services capabilities support the adoption of our subscription offerings. As a result, our sales efforts have been focused primarily on our subscription offering, rather than the profitability of our professional services business. Our professional services are generally priced on a fixed-fee basis and the costs incurred to complete these services, which consist mainly of personnel-related costs, have been greater than the amount charged to the customer. We also do not have standalone selling price for our implementation services for accounting purposes. Accordingly, we recognize implementation services revenue in the same manner as the associated subscription revenue. Prior to launching an individual customer, we incur significant costs associated with implementation activities, which we record as cost of revenue.

Seasonality.  We have historically observed seasonality related to employee benefits cycles as a significantly higher proportion of our customers enter into new subscription agreements with us in the second half of the year, compared to the first half of the year. As we continue to leverage our channel relationships and expand our business, there is no assurance this seasonality will continue. The impact from any seasonality in our new customer agreements is not immediately apparent in our revenue because we do not begin recognizing revenue from new customer agreements until we have implemented our offering, based on the implementation timelines discussed above.

Revenue recognized in any quarter is primarily from customer agreements entered into in prior quarters. In addition, the mix of customers paying monthly, quarterly, or annually varies from quarter to quarter and impacts our deferred revenue balance. As a result of variability in our billing and implementation timelines, the deferred revenue balance does not represent the total value of our customer contracts, nor do changes in deferred revenue serve as a reliable indicator of our future subscription revenue.
Key Business Metrics
We review a number of operating metrics, including the following key metrics, to evaluate our business, measure our performance, identify trends affecting our business, and make strategic decisions.

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Signed Annual Recurring Revenue

								
 	As of June 30,	
 	2018	 	2017	
 	 (in millions)	
Signed Annual Recurring Revenue	$	166.4		 	$	150.8		

Revenue recognized in any quarter is largely derived from customer agreements signed in prior quarters. Accordingly, management measures sales performance and forecasts future subscription revenue based on signed Annual Recurring Revenue (“ARR”). ARR is a forward-looking metric based on contractual terms in existence as of the applicable ARR measurement date and is subject to change resulting from a number of factors including, but not limited to, addition of new customers, changes in user counts, terminations or non-renewals, renewal terms as well as upsells and cross-sells. As discussed above, we begin recognizing revenue from new customer agreements when we have implemented our offering, which can take from approximately 3 to 12 months after entering into an agreement with a customer.

ARR represents the annualized value of subscription revenue under contract with customers at the end of a quarter, which we refer to for this purpose as a measurement date. To calculate ARR, we first calculate the annualized subscription value for each signed customer (whether implemented or not), as of the applicable measurement date, by multiplying the monthly contract value of the subscription services under contract by 12. We exclude from this calculation any customers that have provided us with formal notice of termination or non-renewal as of the measurement date. ARR does not take into account the (i) potential for customers to terminate, or decline to renew, their agreements with us, (ii) achievement of non-recurring or yet-to-be-earned performance guarantees, (iii) one-time engagement bonuses included within our customer contracts or (iv) revenues related to professional services, such as implementation and communications services. ARR is not determined in reference to GAAP.

Our ARR as of June 30, 2018 was $166.4 million , compared with $150.8 million as of June 30, 2017 , representing an increase of approximately 10% , primarily attributable to new customers and renewals. Subsequent to June 30, 2018, we received notification of non-renewal from one of our largest customers, as a result, we expect ARR to decline in the near term .

Annual Net Dollar Retention Rate

						
 	Twelve Months Ended December 31,	
 	2017	 	2016	
Annual Net Dollar Retention Rate	104	%	 	94	%	

We assess our performance on customer retention by measuring our Annual Net Dollar Retention rate (“NDR”). We believe that our ability to retain our customers and expand their subscription revenue growth over time will be an indicator of the stability of our revenue base and the long-term value of our customer relationships. Our NDR provides a measurement of our ability to increase revenue across our existing customer base through expansion of our additional products to existing customers, increases in user counts for existing customers and customer renewals, as offset by terminations or pricing changes. We calculate NDR for a given period as the aggregate annualized subscription contract value as of the last day of that year from those customers that were also customers as of the last day of the prior year, divided by the aggregate annualized subscription contract value from all customers as of the last day of the prior year. In calculating NDR, we exclude one-time fees. NDR does not include subscriptions by new customers contracted since the end of the most recently completed year. We observed an annual net dollar retention rate of 104% and 94% for our signed customer base, for the years ended December 31, 2017 and 2016 , respectively. The year over year increase in NDR was primarily due to the cross-sales of Jiff products into the legacy Castlight customer base.

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Components of Results of Operations
Revenue

We generate revenue from subscription fees from customers for access to the products they select, including basic customer service support. We also earn revenue from professional services primarily related to the implementation of our offering, including extensive communications support to drive adoption by our customers’ employees and their dependents, products sold through our online marketplace and add-on subscription products made available from our other ecosystem partners.
Historically, we have derived a substantial majority of our subscription revenue from our legacy core Castlight platform (now marketed as “Care Guidance Navigator”). Our subscription fees are based primarily on the number of employees and adult dependents that employers identify as eligible to use our offering, which typically includes all of our customers’ employees and adult dependents that receive health benefits.
Typically, we recognize subscription fees on a straight-line basis ratably over the contract term beginning when our products are implemented and ready for launch. Our customer agreements generally have a term of three years. We generally invoice our customers in advance on a monthly, quarterly or annual basis. Amounts that have been invoiced are initially recorded as deferred revenue. Amounts that have not been invoiced and the related revenues have been recognized are reflected as contract assets, recorded as accounts receivable in our condensed consolidated financial statements.

As a result of variability in our billing terms, the deferred revenue balance does not represent the total value of our customer contracts, nor do changes in deferred revenue serve as a reliable indicator of our future subscription revenue in a given period.
Costs of Revenue

Cost of revenue consists of the cost of subscription revenue and cost of professional services revenue.

Cost of subscription revenue primarily consists of data fees, employee-related expenses (including salaries, benefits and stock-based compensation), hosting costs of our cloud-based service, cost of subcontractors, expenses for service delivery (which includes call center support), amortization of internal-use software, depreciation of owned computer equipment and software, amortization of intangibles related to developed technology and backlog, and allocated overhead.

Cost of professional services and other revenue consists primarily of employee-related expenses (including salaries, bonuses, benefits and stock-based compensation) associated with these services, the cost of subcontractors, travel costs and allocated overhead. The time and costs of our customer implementations vary based on the source and condition of the data we receive from third parties, the configurations that we agree to provide and the size of the customer.

Our cost of subscription revenue is expensed as we incur the costs. The cost of professional services and other revenue, to the extent they are incurred and are directly attributable to fulfillment of performance obligations under a customer contract, are deferred and amortized over the benefit period of five years.

Operating Expenses

Operating expenses consist of sales and marketing, research and development and general and administrative expenses.
Sales and Marketing. Sales and marketing expenses consist primarily of employee-related expenses (including salaries, sales commissions and bonuses, benefits and stock-based compensation), travel-related expenses, marketing programs, amortization of intangibles related to customer relationships and allocated overhead. All commissions earned by our sales force and third party referral fees are deferred and amortized generally over a period of five years.

Research and Development. Research and development expenses consist primarily of employee-related expenses (including salaries, bonuses, benefits and stock-based compensation), costs associated with subcontractors and allocated overhead.
General and Administrative. General and administrative expenses consist primarily of employee-related expenses (including salaries, bonuses, benefits and stock-based compensation) for finance and accounting, legal, human resources and

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management information systems personnel, legal costs, professional fees, other corporate expenses, acquisition-related costs, and allocated overhead.
Overhead Allocation. Expenses associated with our facilities and IT costs are allocated between cost of revenues and operating expenses based on employee headcount determined by the nature of work performed.
Results of Operations
The following tables set forth selected consolidated statements of operations data and such data as a percentage of total revenue for each of the periods indicated:

												
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	2017	 	2018	 	2017	
 		 	(as adjusted) (1)	 		 	(as adjusted) (1)	
Revenue:	 	 	 	 	 	 	 	
Subscription	92	 %	 	93	 %	 	91	 %	 	93	 %	
Professional services and other	8	 %	 	7	 %	 	9	 %	 	7	 %	
Total revenue, net	100	 %	 	100	 %	 	100	 %	 	100	 %	
Cost of revenue:	 	 	 	 	 	 	 	
Cost of subscription	24	 %	 	24	 %	 	24	 %	 	20	 %	
Cost of professional services and other	18	 %	 	14	 %	 	17	 %	 	14	 %	
Total cost of revenue	42	 %	 	38	 %	 	41	 %	 	34	 %	
Gross margin percentage	58	 %	 	62	 %	 	59	 %	 	66	 %	
Operating expenses:	 	 	 	 	 	 	 	
Sales and marketing	35	 %	 	49	 %	 	37	 %	 	50	 %	
Research and development	43	 %	 	46	 %	 	43	 %	 	43	 %	
General and administrative	17	 %	 	21	 %	 	18	 %	 	26	 %	
Total operating expenses	95	 %	 	116	 %	 	98	 %	 	119	 %	
Operating loss	(37	)%	 	(54	)%	 	(39	)%	 	(53	)%	
Other income, net	—	 %	 	—	 %	 	1	 %	 	—	 %	
Loss before income taxes	(37	)%	 	(54	)%	 	(38	)%	 	(53	)%	
Income tax benefit	—	 %	 	(16	)%	 	—	 %	 	(9	)%	
Net loss	(37	)%	 	(38	)%	 	(38	)%	 	(44	)%	
_______________________
(1) Prior-period information has been adjusted for the adoption of ASU No. 2014-09, Revenue from Contracts with Customers (“ASC 606”). See Note 2 – Accounting Standards and Significant Accounting Policies to the condensed consolidated financial statements for a summary of adjustments.

Revenue     

																												
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 		 	% 	 	$ 	 	2018	 	 	 	% 	 	$ 	
 		 	2017 (1)	 	Change	 	Change	 		 	2017 (1)	 	Change	 	Change	
 	(In thousands, except percentages)	
Revenue:	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	
Subscription	$	34,802		 	$	30,382		 	15%	 	$	4,420		 	$	67,791		 	$	56,279		 	20%	 	$	11,512		
Professional services and other	2,982		 	2,250		 	33%	 	732		 	6,472		 	4,056		 	60%	 	2,416		
Total revenue, net	$	37,784		 	$	32,632		 	16%	 	$	5,152		 	$	74,263		 	$	60,335		 	23%	 	$	13,928		
_______________________
(1) Prior-period information has been adjusted for the adoption of ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies  to the condensed consolidated financial statements for a summary of adjustments.

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Total revenue for the three months ended June 30, 2018 increased by $5.2 million , or 16% , primarily due to customer launches that occurred in the trailing twelve months ended June 30, 2018 , which contributed $3.6 million of the increase in total revenue year over year, including the impact of customers acquired through Jiff. In addition, a $0.5 million increase is due to professional services revenue related to our Anthem local business initiatives.

Total revenue for the six months ended June 30, 2018 increased by $13.9 million , or 23% , primarily attributable to customer launches that occurred in the trailing twelve months ended  June 30, 2018  which contributed $9.4 million of the increase in total revenue year over year, including the impact of customers acquired through Jiff. The remaining increase was primarily due to $1.9 million of professional services revenue related to our Anthem local business initiatives.

Costs and Operating Expenses

	
																														
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	 	 	% 	 	$	 	2018	 	 	 	% 	 	$ 	
 		 	2017 (1)	 	Change	 	 Change	 		 	2017 (1)	 	Change	 	Change	
 	(In thousands, except percentages)	
Cost of revenue:	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	
Subscription	$	9,140		 	$	7,706		 	19	%	 	$	1,434		 	18,314		 	$	11,952		 	53	%	 	$	6,362		
Professional services and other	6,590		 	4,628		 	42	%	 	1,962		 	12,359		 	8,437		 	46	%	 	3,922		
Total cost of revenue	$	15,730		 	$	12,334		 	28	%	 	$	3,396		 	$	30,673		 	$	20,389		 	50	%	 	$	10,284		
Gross margin (loss) percentage:	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	
Subscription	74	 %	 	75	 %	 	 	 	 	 	73	 %	 	79	 %	 	 	 	 	
Professional services and other	(121	)%	 	(106	)%	 	 	 	 	 	(91	)%	 	(108	)%	 	 	 	 	
Total gross margin	58	 %	 	62	 %	 	 	 	 	 	59	 %	 	66	 %	 	 	 	 	
Gross profit	$	22,054		 	$	20,298		 	9	%	 	$	1,756		 	$	43,590		 	$	39,946		 	9	%	 	$	3,644		
_______________________
(1) Prior-period information has been adjusted for the adoption of ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies to the condensed consolidated financial statements for a summary of adjustments.
Cost of subscription revenue for the three months ended June 30, 2018 increased by $1.4 million , or 19% . The overall increase was primarily due to an increase of $1.2 million in employee compensation-related costs driven by headcount growth and $0.6 million in third-party service fees, partially offset by a decrease of $0.3 million in data fees. All of these cost increases are driven by the increase in our growing customer base.
Cost of subscription revenue for the six months ended June 30, 2018 increased by $6.4 million , or 53% , primarily due to increases of $3.8 million in employee compensation-related costs and $1.1 million of third-party service fees to support customer launches. All of these cost increases are driven by the increase in our growing customer base. Additionally, amortization of acquired intangibles increased by $0.7 million.

Cost of professional services revenue for the three months ended June 30, 2018 increased by $2.0 million or 42% , year over year. The increase is primarily due to a $2.1 million increase in employee compensation-related costs, arising primarily from headcount growth to support our growing customer base.

Cost of professional services revenue for the six months ended June 30, 2018 increased by $3.9 million , or 46% , primarily due to a $3.5 million increase in employee compensation-related costs and a $0.5 million increase in third party service fees. Increases in these costs are driven by headcount growth to support our growing customer base.

Gross margin for the three and six months ended June 30, 2018 decreased due to our investment in professional services and user support teams to support our growing customer base.

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Sales and Marketing

	
																														
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	 	 	% 	 	$ 	 	2018	 	 	 	% 	 	$ 	
 		 	2017 (1)	 	Change	 	Change	 		 	2017 (1)	 	Change	 	Change	
 	(In thousands, except percentages)	
Sales and marketing	$	13,306		 	$	15,935		 	(16	)%	 	$	(2,629	)	 	$	27,218		 	$	30,081		 	(10	)%	 	$	(2,863	)	
_______________________
(1) Prior-period information has been adjusted for the adoption of ASC 606. See Note 2 – Accounting Standards and Significant Accounting Policies to the condensed consolidated financial statements for a summary of adjustments.

Sales and marketing expense for the three months ended June 30, 2018  decreased by $2.6 million , or 16% , primarily due to decreases of $2.1 million in employee compensation-related costs, and restructuring costs of $0.4 million. These decreases were primarily due to the non-recurrence of charges that resulted from the acquisition of Jiff in the same period last year.
 
Sales and marketing expense for the six months ended June 30, 2018  decreased by $2.9 million , or 10% , primarily due to a decrease in employee compensation-related costs of $3.9 million. This decrease was primarily due to the non-recurrence of charges that resulted from the acquisition of Jiff in the same period last year and was partially offset by an increase in referral fees of $1.5 million.
    
Research and Development

																														
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	 	 	% 	 	$ 	 	2018	 	 	 	%	 	$ 	
 		 	2017	 	Change	 	Change	 		 	2017	 	Change	 	Change	
 	(In thousands, except percentages)	
Research and development	$	16,425		 	$	15,194		 	8	%	 	$	1,231		 	$	31,796		 	$	26,265		 	21	%	 	$	5,531		

Research and development expense for the three months ended June 30, 2018 increased by  $1.2 million , or  8% . The overall increase was primarily due to an increase in third-party fees of $1.0 million for product enhancements.

Research and development expense for the six months ended June 30, 2018 increased by  $5.5 million , or  21% , primarily attributable to increases in employee compensation-related costs of $2.7 million, third-party fees of $1.3 million for product enhancements and hosting costs of $0.5 million.

General and Administrative

																														
 	Three Months Ended June 30,	 	Six Months Ended June 30,	
 	2018	 	 	 	% 	 	$ 	 	2018	 	 	 	% 	 	$	
 		 	2017	 	Change	 	Change	 		 	2017	 	Change	 	Change	
 	(In thousands, except percentages)	
General and administrative	$	6,382		 	$	6,766		 	(6	)%	 	$	(384	)	 	$	13,207		 	$	15,764		 	(16	)%	 	$	(2,557	)	

General and administrative expense for the three months ended June 30, 2018 decreased by $0.4 million , or  6% , primarily due to decreased use of third-party services.

General and administrative expense for the six months ended June 30, 2018 decreased by  $2.6 million , or  16% , primarily due to the non-recurrence of $2.5 million in costs related to the acquisition of Jiff in the second quarter of 2017.

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Liquidity and Capital Resources

	
								
 	Six Months Ended June 30,	
 	2018	 	2017 (1)	
 	(In thousands)	
Net cash used in operating activities	$	(20,086	)	 	$	(15,026	)	
Net cash provided by investing activities	1,167		 	28,768		
Net cash provided by financing activities	2,242		 	100		
Net (decrease) increase in cash, cash equivalents and restricted cash	$	(16,677	)	 	$	13,842		
_______________________
(1) Prior-period information has been adjusted for the adoption of ASU No. 2014-09, Revenue from Contracts with Customers (“ASC 606”). See Note 2 to the condensed consolidated financial statements for a summary of adjustments.
As of June 30, 2018 , our principal sources of liquidity were cash, cash equivalents and marketable securities totaling $74.5 million , which were held for working capital purposes. Our cash, cash equivalents and marketable securities are comprised primarily of U.S. agency obligations, U.S. treasury securities and money market funds.
Since our inception, we have financed our operations primarily through sales of equity securities and, to a lesser extent, payments from our customers. We believe that our existing cash, cash equivalents and marketable securities will be sufficient to meet our working capital and capital expenditure needs for at least the next 12 months. Our future capital requirements will depend on many factors including our growth rate, subscription renewal activity, the timing and extent of spending to support development efforts, integration costs related to the acquisition of Jiff, our expansion of sales and marketing activities, the introduction of new and enhanced services offerings and the continuing market acceptance of our cloud-based products. Although we currently are not a party to any agreement and do not have any understanding with any third parties with respect to potential investments in, or acquisitions of, businesses or technologies, w e may in the future enter into these types of arrangements.
On April 3, 2017, Castlight, Jiff and Silicon Valley Bank agreed to refinance the existing term loan facility owed by Jiff to the Silicon Valley Bank. The loan agreement provides for an approximately $5.6 million term loan and up to a $25 million revolving credit facility. Refer to Note 10 to the condensed consolidated financial statements for further information on our debt.
We may be required to seek additional equity or debt financing. In the event that additional financing is required from outside sources, we may not be able to raise it on terms acceptable to us, or at all. If we are unable to raise additional capital when desired, our business, operating results and financial condition would be adversely affected.
Operating Activities
Cash used in operating activities for the six months ended June 30, 2018 and 2017 was $20.1 million and $15.0 million , respectively. The increase in cash used in operations resulted primarily from increased headcount. Cash used in operations reflected our net loss of $28.4 million for the six months ended June 30, 2018 , adjusted by $22.8 million in non-cash expenses, including stock-based compensation of $9.7 million , amortization of deferred costs of $7.9 million , depreciation and amortization of $3.6 million and lease exit charges of $1.8 million . Working capital uses of cash included an increase in accounts receivable of $6.3 million , primarily as a result of the timing of billings and collections. Other uses of cash included an increase in other assets of $1.9 million , a decrease in accounts payable and other accruals of $0.7 million and a decrease in deferred revenue of $1.2 million , primarily as a result of an increase in the amount recognized as revenues year-over-year.
Investing Activities
Cash provided by investing activities for the six months ended June 30, 2018 and  2017 was $1.2 million and $28.8 million , respectively. Net cash provided by investing activities was primarily attributable to $2.5 million of maturities, purchases and sales of marketable securities, partially offset by purchases of $1.3 million of property and equipment.

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Financing Activities
Cash provided by financing activities for the six months ended June 30, 2018 and 2017 was $2.2 million and $0.1 million , res pectively. Net cash provided by financing activities during the six months ended June 30, 2018 was due to proceeds from the exercise of employee stock options .
Contractual Obligations and Commitments
Our principal commitments primarily consist of obligations under leases for office space and a term loan facility with Silicon Valley Bank and co-location facilities for data center capacity. Our existing lease agreements provide us with the option to renew and generally provide for rental payments on a graduated basis. Our future operating lease obligations would change if we entered into additional operating lease agreements as we expand our operations and if we exercised these options. See Note 10 – Debt and Note 12 – Commitments and Contingencies to the condensed consolidated financial statements for a discussion of our term loan and lease commitments, respectively. There were no other material changes in the Company’s contractual obligations from those disclosed in its Annual Report on Form 10-K for the year ended December 31, 2017 other than those discussed in Note 12 – Commitments and Contingencies to the condensed consolidated financial statements.

Other than the term loan and lease commitments discussed in Note 10 – Debt and Note 12 – Commitments and Contingencies , respectively, to the condensed consolidated financial statements, we do not have commitments under lines of credit, or other such debt arrangements. We do not have any material non-cancelable purchase commitments as of  June 30, 2018 .
Off-Balance Sheet Arrangements
During the periods presented, we did not have, nor do we currently have, any relationships with unconsolidated entities or financial partnerships, such as entities often referred to as structured finance or special purpose entities, which would have been established for the purpose of facilitating off-balance sheet arrangements or other contractually narrow or limited purposes. We are therefore not exposed to the financing, liquidity, market or credit risk that could arise if we had engaged in those types of relationships.
Critical Accounting Policies and Estimates

Effective January 1, 2018, we adopted ASC 606. Except for the accounting policies for use of estimates, revenue recognition, accounts receivable, deferred commissions, and deferred professional service costs that were updated as a result of adopting ASC 606, as described in Note 2 – Accounting Standards and Significant Accounting Policies of the notes to the condensed consolidated financial statements, there were no significant changes to our critical accounting policies and estimates during the six months ended June 30, 2018 , as described in our Annual Report on Form 10-K for the year ended December 31, 2017 .

Item 3. Quantitative and Qualitative Disclosures About Market Risk
Interest Rate Sensitivity
We had cash, cash equivalents and marketable securities totaling $74.5 million as of June 30, 2018 and $93.3 million as of December 31, 2017 . These are invested primarily in U.S. agency obligations, U.S. treasury securities and money market funds. The cash, cash equivalents and short-term marketable securities are held for working capital and other general corporate purposes. Our investments are made for capital preservation purposes. We do not enter into investments for trading or speculative purposes. All our investments are denominated in U.S. dollars.
Our cash equivalents and our portfolio of marketable securities are subject to market risk due to changes in interest rates. Fixed rate securities may have their market value adversely affected due to a rise in interest rates, while floating rate securities may produce less income than expected if interest rates fall. Due in part to these factors, our future investment income may fall short of expectations due to changes in interest rates or we may suffer losses in principal if we are forced to sell securities that decline in market value due to changes in interest rates. However, because we classify our marketable

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securities as “available for sale,” no gains or losses are recognized due to changes in interest rates unless such securities are sold prior to maturity or declines in fair value are determined to be other-than-temporary. Our fixed-income portfolio is subject to interest rate risk.
An immediate increase of 100-basis points in interest rates would have resulted in a $0.1 million market value reduction in our investment portfolio as of June 30, 2018 . All of our investments earn less than 100-basis points and as a result, an immediate decrease of 100-basis points in interest rates would have increased the market value by $0.1 million as of June 30, 2018 . This estimate is based on a sensitivity model that measures market value changes when changes in interest rates occur. Fluctuations in the value of our investment securities caused by a change in interest rates (gains or losses on the carrying value) are recorded in other comprehensive income, and are realized only if we sell the underlying securities.

We also have interest rate exposure as a result of our loan agreement, which provides a term loan and revolving credit facility, as described in Note 10 – Debt to the condensed consolidated financial statements. We currently do not hedge this risk. As of June 30, 2018 , we had $5.6 million of borrowings outstanding under the term loan and no borrowings outstanding under the revolver. Borrowings outstanding under the term loan and revolver are subject to variable interest rates based on the prime rate as published in the money rates section of The Wall Street Journal. Changes in the prime rate will affect the interest on borrowings under the loan agreement. However, a 50-basis point increase in the interest rate on the term loan would not materially increase interest expense during 2018.

Item 4. Controls and Procedures

Evaluation of Disclosure Controls and Procedures

Our management, with the supervision and participation of our principal executive officer and principal financial officer, evaluated the effectiveness of our disclosure controls and procedures, as defined in Rules 13a-15(e) and 15d-15(e) under the Securities Exchange Act of 1934, as amended (the Exchange Act), as of the end of the period covered by this report.

In designing and evaluating the disclosure controls and procedures, management recognizes that any controls and procedures, no matter how well designed and operated, can provide only reasonable assurance of achieving the desired control objectives. In addition, the design of disclosure controls and procedures must reflect the fact that there are resource constraints and that management is required to apply its judgment in evaluating the benefits of possible controls and procedures relative to their costs.

Based on our management’s evaluation, our principal executive officer and principal financial officer concluded that, as of June 30, 2018 , our disclosure controls and procedures were designed at a reasonable assurance level and were effective to provide reasonable assurance that information we are required to disclose in reports that we file or submit under the Exchange Act is recorded, processed, summarized, and reported within the time periods specified in Securities and Exchange Commission rules and forms, and that such information is accumulated and communicated to our management, including our chief executive officer and chief financial officer, as appropriate, to allow timely decisions regarding required disclosure.

Changes in Internal Control over Financial Reporting

In January 2018, we implemented changes to our revenue recognition policies and processes to support the adoption of ASU 2014-09,  Revenue from Contracts with Customers (“ASC 606”) .  We have also updated internal controls over financial reporting to ensure compliance with the new accounting and disclosure rules.

Part II. OTHER INFORMATION
Item 1. Legal Proceedings
    
From time to time, the Company may become subject to other legal proceedings, claims or litigation arising in the ordinary course of business. In addition, the Company may receive letters alleging infringement of patents or other intellectual

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property rights. If an unfavorable outcome were to occur in litigation, the impact could be material to the Company’s business, financial condition, cash flow or results of operations, depending on the specific circumstances of the outcome. The Company accrues for loss contingencies when it is both probable that it will incur the loss and when it can reasonably estimate the amount of the loss or range of loss.

Item 1A. Risk Factors

The risks and uncertainties described below are not the only ones we face. Additional risks and uncertainties that we are unaware of, or that we currently believe are not material, may also become important factors that adversely affect our business. If any of the following risks actually occur, our business, financial condition, results of operations and future prospects could be materially and adversely affected. In that event the market price of our Class B common stock could decline, and you could lose part or all of your investment.
Risks Related to Our Business
We rely on channel partners for a substantial portion of our sales, and if our channel partner relationships are unsuccessful then our sales results will be adversely affected and the growth of our business will be harmed.
Our sales strategy relies in part on relationships we have developed with health plans, benefits consultants, brokers and other industry participants, and we are continuing to invest in, and expect to continue to increase our reliance on, these relationships with channel partners to access customers and grow our overall sales. However, there can be no assurance that our channel partner relationships will be successful, or will result in access to additional customers or growth in sales. Our channel partnerships do not always meet our expectations and could fail for a variety of reasons, including changes in our partners’ business priorities, insufficient or misaligned incentives for our partners’ to assist us with sales, competition, or other factors.

In addition, our reliance on sales through channel partners could put downward pressure on the total revenue we are able to generate, and could result in existing customers electing to use alternative or lower-functionality versions of our products that we may elect to provide through channel partners. The concentration of a material portion of business with any given channel partner could also create tensions with other companies we do business with, including health plans on whom we rely to receive data and offer our services.

Certain relationships we will enter or have entered into with channel partners will require substantial investments of our resources to support these initiatives.  There can be no assurance that the investments we make to develop and support these channel relationships, or the effort required to do so, will provide a positive return on our investment in the near term, or at all.  If any of these events materialize, our business and results of operations could be materially adversely affected.
If our new products and services are not adopted by our customers, or if we fail to continue to innovate and develop new products and services that are adopted by customers, then our revenue and operating results will be adversely affected.
Prior to our acquisition of Jiff, we derived a substantial majority of our revenue from sales of our legacy care guidance platform, and our longer-term operating results and continued growth depend in part on our ability to successfully develop and sell new products and services that our new and existing customers want and are willing to purchase. In addition to our legacy core Castlight platform (now marketed as our care guidance solution), we continue to introduce a number of products and cross-sells, such as our latest offering of Castlight Complete, Care Guidance, Wellbeing, Elevate and Engage, but it is uncertain whether these products and services will result in significant revenue or comprise a significant portion of our total revenue. In addition, based on our belief that our customers are interested in acquiring wellness-related products, we have devoted substantial efforts to our acquisition of Jiff, and expect to continue to devote substantial efforts to the integration and expansion of the Jiff business. We have also invested, and will continue to invest, significant resources in research and development to enhance our existing offering and introduce new high quality products and services. If existing customers are not willing to make additional payments for such new products, or if new customers do not value such new products, our business and operating results will be harmed. If we are unable to predict user preferences or our industry changes, or if we are unable to modify our offering and services on a timely basis, we might lose customers. Our operating results would also suffer if our innovations are not responsive to the needs of our customers, appropriately timed with market opportunity or effectively communicated and brought to market.

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If our existing customers do not continue or renew their agreements with us, renew at lower fee levels or decline to purchase additional products and services from us, our business and operating results will suffer.
We expect to derive a significant portion of our revenue from renewal of existing customer agreements and sales of additional products and services to existing customers. Revenue recognized in any quarter is largely derived from customer agreements signed in prior quarters. As a result, achieving a high renewal rate of our customer agreements and selling additional products and services is critical to our future operating results.
We may experience significantly more difficulty than we anticipate in renewing existing customer agreements or in renewing them upon favorable terms, particularly as we seek to convert customers who initially purchased our transparency-only offering to our full platform offering. Factors that may affect the renewal rate for our offering, terms of those renewals and our ability to sell additional products and services include:
		
•	the price, performance and functionality of our offering;	
		
•	our customers’ user counts and benefit design features;	
		
•	the availability, price, performance and functionality of competing or alternative solutions;	
		
•	the potential for customers that are able to access lower-functionality versions of our offering that we provide through health plans or other channel partners to opt to use the lower-functionality versions of our offering;	
		
•	our ability to develop complementary products and services;	
		
•	our continued ability to access the pricing and claims data necessary to enable us to deliver reliable data in our cost estimation and price transparency offering to customers;	
		
•	the stability, performance and security of our hosting infrastructure and hosting services;	
		
•	changes in health care laws, regulations or trends; and	
		
•	the business environment of our customers, in particular, headcount reductions by our customers.	

We enter into master services agreements with our customers. These agreements generally have stated terms of three years. Our customers have no obligation to renew their subscriptions for our offering after the term expires. In addition, our customers may negotiate terms less advantageous to us upon renewal, which may reduce our revenue from these customers. Factors that are not within our control may contribute to a reduction in our contract revenue. For instance, our customers may reduce their number of employees, which would result in a corresponding reduction in the number of employee users eligible for our offering and thus a lower aggregate monthly services fee. Our future operating results also depend, in part, on our ability to sell new products and services to our existing customers. If our customers fail to renew their agreements, renew their agreements upon less favorable terms or at lower fee levels, or fail to purchase new products and services from us, our revenue may decline or our future revenue may be constrained.
    
In addition, a significant number of our customer agreements allow customers to terminate such agreements for convenience at certain times, typically with one to three months advance notice. We typically incur the expenses associated with integrating a customer’s data into our health care database and related training and support prior to recognizing meaningful revenue from such customer. Customer subscription revenue is not recognized until our products are implemented for launch, which is generally from three to 12 months from contract signing. If a customer terminates its agreement early and revenue and cash flows expected from a customer are not realized in the time period expected or not realized at all, our business, operating results and financial condition could be adversely affected.
We operate in a competitive industry, and if we are not able to compete effectively, our business and operating results will be harmed.
    
The market for our products and services is competitive, and we expect the market to attract increased competition, which could make it hard for us to succeed. We currently face competition for portions of our offering from a range of companies, including healthcare information technology companies and specialized software and solution providers that offer similar solutions, often at substantially lower prices, and that are continuing to develop additional products and becoming more sophisticated and effective. Our market is in an early stage of development, but is rapidly evolving and competitive. We currently face competition from both existing and emerging vendors across a variety of categories, from specialists in the care guidance and wellbeing areas of the market, to broader offerings that compete with our full healthcare navigation platform. There are a number of independent companies we compete with across the various functions of our health navigation platform. Care guidance competitors include Accolade, ClearCost Health, Compass, Healthcare Bluebook, and Quantum Health. Wellbeing competitors include Limeade, Redbrick Health, VirginPulse, and Vitality. Platform competitors include Evive, HealthAdvocate, Sharecare, and Welltok.

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      In addition, large, well-financed health plans, with whom we cooperate and on whom we depend in order to obtain the pricing and claims data we need to deliver our offering to customers, have in some cases developed their own wellbeing and care guidance tools and provide these solutions to their customers at discounted prices or often for free. These health plans include, for example, Aetna Inc., Cigna Corporation, Health Services Corporation, and UnitedHealth Group, Inc. Competition from specialized software and solution providers, health plans and other parties may result in pricing pressure, which may lead to price decline in certain product segments, which could negatively impact our sales, profitability and market share. In addition, if health plans perceive continued cooperation with us as a threat to their business interests, they may take steps that impair our access to pricing and claims data, or that otherwise make it more difficult or costly for us to deliver our offering to customers.

Some of our competitors, in particular health plans, have greater name recognition, longer operating histories and significantly greater resources than we do. Furthermore, our current or potential competitors may be acquired by third parties with greater available resources. As a result, our competitors might be able to respond more quickly and effectively than we can to new or changing opportunities, technologies, standards or customer requirements and may have the ability to initiate or withstand substantial price competition. In addition, current and potential competitors have established, and might in the future establish, cooperative relationships with vendors of complementary products, technologies or services to increase the availability of their solutions in the marketplace. The field of healthcare and the services related to healthcare are subject to change, and there has been consolidation in the industry. Accordingly, new competitors or alliances might emerge that have greater market share, a larger customer base, more widely adopted proprietary technologies, greater marketing expertise, greater financial resources and larger sales forces than we have, which could put us at a competitive disadvantage. Our competitors could also be better positioned to serve certain segments of our market, such as customers that desire a more narrow solution, which could create additional price pressure. In light of these factors, even if our offering is more effective than those of our competitors, current or potential customers might accept competitive offerings in lieu of purchasing our offerings.
Our proprietary software may not operate properly, which could damage our reputation, give rise to claims against us or divert application of our resources from other purposes, any of which could harm our business and operating results.

Proprietary software development is time-consuming, expensive and complex, and may involve unforeseen difficulties. We may encounter technical obstacles, and it is possible that we will discover additional problems that prevent our proprietary products from operating properly. We are currently developing new features and services in our proprietary software, including our Complete Health, Wellbeing, Care Guidance, Elevate and Engage. If our offering does not function reliably or fails to achieve customer expectations in terms of performance, customers could assert liability claims against us or attempt to cancel their contracts with us. This could damage our reputation and impair our ability to attract or maintain clients which would adversely affect our operating results.
    
Moreover, data services that are as complex as those we offer have in the past contained, and may in the future develop or contain, undetected defects or errors. Material performance problems, defects or errors in our existing or new software and products and services may arise in the future and may result from interface of our offering with systems and data that we did not develop and the function of which is outside of our control or undetected in our testing. These defects and errors and any failure by us to identify and address them could result in loss of revenue or market share, diversion of development resources, injury to our reputation and increased service and maintenance costs. Defects or errors in our health benefits platform might discourage existing or potential customers from purchasing our offering from us. Correction of defects or errors could prove to be impossible or impracticable. The costs incurred in correcting any defects or errors may be substantial and could adversely affect our operating results.
Any failure to offer high-quality technical support services may adversely affect our relationships with our customers and harm our financial results.
Our customers depend on our support organization to resolve any technical issues relating to our offering. In addition, our sales process is highly dependent on the quality of our offering, our business reputation and on strong recommendations from our existing customers. Any failure to maintain high-quality and highly-responsive technical support, or a market perception that we do not maintain high-quality and highly-responsive support, could harm our reputation, adversely affect our ability to sell our offering to existing and prospective customers, and harm our business, operating results and financial condition.

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We offer technical support services with our offering and may be unable to respond quickly enough to accommodate short-term increases in customer demand for support services, particularly as we increase the size of our customer base. We also may be unable to modify the format of our support services to compete with changes in support services provided by competitors. It is difficult to predict customer demand for technical support services and if customer demand increases significantly, we may be unable to provide satisfactory support services to our customers and their employees. Additionally, increased customer demand for these services, without corresponding revenue, could increase costs and adversely affect our operating results.
If we cannot implement our offering for customers in a timely manner, we may lose customers and our reputation may be harmed.
Our customers have a variety of different data formats, enterprise applications and infrastructure and our offering must support our customers’ data formats and integrate with complex enterprise applications and infrastructures. If our platform does not currently support a customer’s required data format or appropriately integrate with a customer’s applications and infrastructure, or if an existing customer switches to unsupported infrastructure, then we must configure our platform to do so, which increases our expenses. Additionally, we do not control our customers’ implementation schedules. As a result, if our customers do not allocate internal resources necessary to meet their implementation responsibilities or if we face unanticipated implementation difficulties, the implementation may be delayed. Further, our implementation capacity has at times constrained our ability to successfully implement our offering for our customers in a timely manner, particularly during periods of high demand. If the customer implementation process is not executed successfully or if execution is delayed, we could incur significant costs, customers could become dissatisfied and decide not to increase usage of our offering, or not to use our offering beyond an initial period prior to their term commitment or, in some cases, revenue recognition could be delayed. Our data dependencies and implementation procedures differ for each new product that we launch. Accordingly, our ability to convert sales of new products into billings and revenue depends on our ability to create a scalable launch infrastructure in each case. In addition, competitors with more efficient operating models with lower implementation costs could penetrate our customer relationships.

Additionally, large and demanding enterprise customers, who currently comprise the majority of our customer base, may request or require specific features or functions unique to their particular business processes, which increase our upfront investment in sales and deployment efforts and the revenue resulting from the customers under our typical contract length may not cover the upfront investments. If prospective large customers require specific features or functions that we do not offer, then the market for our offering will be more limited and our business could suffer.

In addition, supporting large customers could require us to devote significant development services and support personnel and strain our personnel resources and infrastructure. Furthermore, if we are unable to address the needs of these customers in a timely fashion or further develop and enhance our offering, or if a customer or its employees are not satisfied with our quality of work, our offering or professional services then we could incur additional costs to address the situation. In addition, we may be required to issue credits or refunds for prepaid amounts related to unused services, the timing of recognition of revenue for, and the profitability of, that work might be impaired and the customer’s dissatisfaction with our offering could damage our ability to expand the number of products and services purchased by that customer. These customers may not renew their agreements, seek to terminate their relationship with us or renew on less favorable terms. Moreover, negative publicity related to our customer relationships, regardless of its accuracy, may further damage our business by affecting our ability to retain or compete for new business with current and prospective customers. If any of these were to occur, our revenue may fail to grow at historical rates or at all, or may even decline, and our operating results could be adversely affected.
If we fail to manage our growth effectively, our expenses could increase more than expected, our revenue may not increase and we may be unable to implement our business strategy.
We have experienced significant growth in recent periods, which puts strain on our business, operations and employees. For example, our revenue has increased from $60.3 million for the six months ended June 30, 2017 to $74.3 million for the six months ended June 30, 2018 . Future revenues may not grow at these same rates or may decline. To manage our current and anticipated future growth effectively, we must continue to maintain and enhance our IT infrastructure, financial and accounting systems and controls. Moreover, we may from time to time decide to undertake cost savings initiatives, such as the reduction in workforce we implemented in 2016 and 2018, or disposing of, or otherwise discontinuing certain products, in an effort to focus our resources on key strategic initiatives and streamline our business. We must also attract, train and retain a significant number

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of qualified personnel in key areas such as research and development, sales and marketing, customer support, professional services, and management, and the availability of such personnel, in particular software engineers, may be constrained. These and similar challenges, and the related costs, may be exacerbated by the fact that our headquarters is located in the San Francisco Bay Area.
A key aspect to managing our growth is our ability to scale our capabilities to implement our offering satisfactorily with respect to both large and demanding enterprise customers, who currently comprise the substantial majority of our customer base, as well as smaller customers. Large customers often require specific features or functions unique to their particular business processes, which at a time of rapid growth or during periods of high demand, may strain our implementation capacity and hinder our ability to successfully implement our offering to our customers in a timely manner. We may also need to make further investments in our technology and automate portions of our offering or services to decrease our costs, particularly as we grow sales of our health benefits platform to smaller customers. If we are unable to address the needs of our customers or their employees, or our customers or their employees are unsatisfied with the quality of our offering or services, they may not renew their agreements, seek to cancel or terminate their relationship with us or renew on less favorable terms. In addition, many of our customers adjust their benefit plan designs, benefits providers and eligibility criteria at the start of each new benefits plan year, requiring additional configurations for those customers. As our customer base grows, the complexity of these activities can increase. If we fail to automate these operations sufficiently and implement these changes on a timely basis or are unable to implement them effectively, our business may suffer.

We may experience additional challenges with managing our growth relating to our acquisition of Jiff. We expect that the operation and integration of the acquired technologies will require substantial financial costs and substantial management attention. If we fail to effectively manage the integration process in a timely manner, our business and financial results may suffer.
Failure to effectively manage our growth could also lead us to over-invest or under-invest in development and operations, result in weaknesses in our infrastructure, systems or controls, give rise to operational mistakes, financial losses, loss of productivity or business opportunities and result in loss of employees and reduced productivity of remaining employees. Our growth is expected to require significant capital expenditures and might divert financial resources from other projects such as the development of new products and services. In addition, data and content fees, which are one of our primary operational costs, are not fixed as they vary based on the source and condition of the data we receive from third parties, and if they remain variable or increase over time, we would not be able to realize the economies of scale that we expect as we grow renewals and implementation of new customers, which may negatively impact our gross margin. If our management is unable to effectively manage our growth, our expenses might increase more than expected, our revenue may not increase or might grow more slowly than expected and we might be unable to implement our business strategy. The quality of our offering might also suffer, which could negatively affect our reputation and harm our ability to retain and attract customers.
We depend on our senior management team, and the loss of one or more of our executive officers or key employees or an inability to attract and retain highly skilled employees or key subcontractor services could adversely affect our business.
Our success depends largely upon the continued services of our key executive officers. These executive officers are at-will employees and therefore may terminate employment with us at any time with no advance notice. We do not maintain “key person” insurance for any of these executive officers or any of our other key employees. We also rely on our leadership team in the areas of research and development, marketing, services and general and administrative functions. From time to time, there may be changes in our executive management team resulting from the hiring or departure of executives, which could disrupt our business. The replacement of one or more of our executive officers or other key employees would likely involve significant time and costs and may significantly delay or prevent the achievement of our business objectives.

To continue to execute our growth strategy, we also must attract and retain highly skilled personnel, particularly in research and development and sales and marketing. Competition is intense for engineers with high levels of experience in designing and developing software and Internet-related services, particularly in the San Francisco Bay Area where we are located. We might not be successful in maintaining our unique culture and continuing to attract and retain qualified personnel. We have from time to time in the past experienced, and we expect to continue to experience in the future, difficulty in hiring and retaining highly skilled personnel with appropriate qualifications. The pool of qualified personnel with Software-as-a-Service, or SaaS, experience or experience working with the health care market is limited overall. In addition, many of the companies with which we compete for experienced personnel have greater resources than we have. We supplement our hired skilled personnel through the use of subcontractors, particularly in the area of research and development, a significant portion

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of which perform services outside of the United States. If these subcontractors cease to perform services for us for any reason, our ability to meet our development goals may be impaired, and our business and future growth prospects could be severely harmed.
In addition, in making employment decisions, particularly in the Internet and high-technology industries, job candidates often consider the value of the stock options or other equity instruments they are to receive in connection with their employment. Volatility or performance trends in the price of our stock might, therefore, adversely affect our ability to attract or retain highly skilled personnel. Furthermore, the requirement to expense stock options and other equity instruments might discourage us from granting the size or type of stock option or equity awards that job candidates require to join our company. If we fail to attract new personnel or fail to retain and motivate our current personnel, our business and future growth prospects could be severely harmed.
Our marketing efforts depend significantly on our ability to receive positive references from our existing customers.
Our marketing efforts depend significantly on our ability to call on our current customers to provide positive references to new, potential customers. Given our limited number of long-term customers, the loss or dissatisfaction of any customer could substantially harm our brand and reputation, inhibit the market adoption of our offering and impair our ability to attract new customers and maintain existing customers. Any of these consequences could have a material adverse effect on our business, financial condition and results of operations.
If our security measures are breached and customer’s data are compromised, our offering may be perceived as insecure, we may incur significant liabilities, our reputation may be harmed and we could lose sales and customers.
Our offering involves the storage and transmission of customers’ proprietary information, personally identifiable information, and protected health information of our customers’ employees and their dependents, which is regulated under the Health Insurance Portability and Accountability Act of 1996 and its implementing regulations, collectively HIPAA. Because of the extreme sensitivity of this information, the security features of our offering are very important. If our security measures, some of which are managed by third parties, are breached or fail, unauthorized persons may be able to obtain access to sensitive customer or employee data, including HIPAA-regulated protected health information. A security breach or failure could result from a variety of circumstances and events, including third-party action, employee negligence or error, malfeasance, computer viruses, attacks by computer hackers, failures during the process of upgrading or replacing software, databases or components thereof, power outages, hardware failures, telecommunication failures, user errors, and catastrophic events.

If our security measures were to be breached or fail, our reputation could be severely damaged, adversely affecting customer or investor confidence, customers may curtail their use of or stop using our offering and our business may suffer. In addition, we could face litigation, damages for contract breach, penalties and regulatory actions for violation of HIPAA and other laws or regulations applicable to data protection and significant costs for remediation and for measures to prevent future occurrences. In addition, any potential security breach could result in increased costs associated with liability for stolen assets or information, repairing system damage that may have been caused by such breaches, incentives offered to customers or other business partners in an effort to maintain the business relationships after a breach and implementing measures to prevent future occurrences, including organizational changes, deploying additional personnel and protection technologies, training employees and engaging third-party experts and consultants. While we maintain insurance covering certain security and privacy damages and claim expenses we may not carry insurance or maintain coverage sufficient to compensate for all liability and such insurance may not be available for renewal on acceptable terms or at all, and in any event, insurance coverage would not address the reputational damage that could result from a security incident.
    
We outsource important aspects of the storage and transmission of customer information, and thus rely on third parties to manage functions that have material cyber-security risks. These outsourced functions include services such as software design and product development, software engineering, database consulting, call center operations, co-location data centers, data-center security, IT, network security and Web application firewall services. We attempt to address these risks by requiring outsourcing subcontractors who handle customer information to sign business associate agreements contractually requiring those subcontractors to adequately safeguard personal health data and in some cases by requiring such outsourcing subcontractors to undergo third-party security examinations. However, we cannot assure you that these contractual measures and other safeguards will adequately protect us from the risks associated with the storage and transmission of customers proprietary and protected health information.

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We may experience cyber-security and other breach incidents that may remain undetected for an extended period. Because techniques used to obtain unauthorized access or to sabotage systems change frequently and generally are not recognized until launched against us, we may be unable to anticipate these techniques or to implement adequate preventive measures. In addition, in the event that our customers authorize or enable third parties to access their data or the data of their employees on our systems, we cannot ensure the complete integrity or security of such data in our systems as we would not control that access. Third parties may also attempt to fraudulently induce our employees or customers and their employees into disclosing sensitive information such as user names, passwords or other information or otherwise compromise our security measures in order to gain access to customer information, which could result in significant legal and financial exposure, a loss of confidence in the security of our offering, interruptions or malfunctions in our operations, and, ultimately, harm to our future business prospects and revenue. Because our offering offers single sign-on capabilities for our customers and their employees to point solutions offered by our partners, unauthorized access to our offering could also result in security breaches of customer information and data in offerings by our partners. We may be required to expend significant capital and financial resources to invest in security measures, protect against such threats or to alleviate problems caused by breaches in security. If an actual or perceived breach of our security occurs, or if we are unable to effectively resolve such breaches in a timely manner, the market perception of the effectiveness of our security measures could be harmed and we could lose sales and customers or suffer other reputational harm.
Regardless of the merits of any such suit, defending it could be costly and divert management’s attention from leading our business.
We have a history of significant losses, which we expect to continue for the foreseeable future, and we may never achieve or sustain profitability in the future.
We have incurred significant net losses in each year since our incorporation in 2008 and expect to continue to incur net losses for at least fiscal year 2018. We experienced net losses of $28.4 million , $51.9 million , $58.7 million , and $79.9 million during the six months ended June 30, 2018 and the years ended December 31, 2017, 2016 and 2015, respectively. As of June 30, 2018 , we had an accumulated deficit of $403.7 million . The losses and accumulated deficit were primarily due to the substantial investments we made to grow our business, enhance our technology and offering through research and development and acquire and support customers. We anticipate that cost of revenue and operating expenses will increase in the foreseeable future as we seek to continue to grow our business, enhance our offering and acquire customers. In addition, as a result of our acquisition of Jiff, we have incurred substantial transaction costs and expect to incur further increases in our cost of revenue and operating expenses in connection with the integration of the Jiff and Castlight functionalities and costs to acquire customers. These efforts may prove more expensive than we currently anticipate, and we may not succeed in increasing our revenue sufficiently to offset these higher expenses. Many of our efforts to generate revenue from our business are new and unproven, and any failure to increase our revenue or generate revenue from new products and services could prevent us from achieving or maintaining profitability. Furthermore, to the extent we are successful in increasing our customer base, we could also incur increased losses because costs associated with entering into customer agreements are generally incurred up front, while customers are generally billed over the term of the agreement. Our prior losses, combined with our expected future losses, have had and will continue to have an adverse effect on our stockholders’ equity and working capital. We expect to continue to incur operating losses for the foreseeable future and may never become profitable on a quarterly or annual basis, or if we do, we may not be able to sustain profitability in subsequent periods. As a result of these factors, we may need to raise additional capital through debt or equity financings in order to fund our operations, which could be dilutive to stockholders, and such capital may not be available on reasonable terms, if at all.
Our limited operating history makes it difficult to evaluate our current business and future prospects.
We were founded in 2008, began building the first version of our care guidance platform in 2009, did not complete our first customer sale and implementation until 2010 and did not make substantial investments in sales and marketing until 2012. Jiff was founded in 2010 and had its first customer implementation in 2013 before being acquired by us in April of 2017. The limited operating histories of these two businesses, standalone and as combined, limit our ability to forecast our future operating results and such forecasts are subject to a number of uncertainties, including our ability to plan for and model future growth.
    
We have encountered and will continue to encounter risks and uncertainties frequently experienced by new and growing companies in rapidly changing industries, such as determining appropriate investments of our limited resources, market adoption of our existing and future offerings, competition from other companies, acquiring and retaining customers,

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managing customer deployments, hiring, integrating, training and retaining skilled personnel, developing new products and services, determining prices for our products, handling unforeseen expenses and managing challenges in forecasting accuracy. If our assumptions regarding these and other similar risks and uncertainties, which we use to plan our business, are incorrect or change as we gain more experience operating our business or due to changes in our industry, or if we do not address these risks and uncertainties successfully, our operating and financial results could differ materially from our expectations and our business could suffer.

In addition, we may need to change our current operations infrastructure in order for us to achieve profitability and scale our operations efficiently, which makes our future prospects even more difficult to evaluate. For example, in order to grow sales of our health benefits platform to smaller customers in a financially sustainable manner, we may need to further automate implementations, tailor our offering and modify our go-to-market approaches to reduce our service delivery and customer acquisition costs. If we fail to implement these changes on a timely basis or are unable to implement them effectively, our business may suffer.

Following our acquisition of Jiff, we may be unable to integrate successfully the technologies of Castlight and Jiff and realize the anticipated benefits of the transaction.

Following the acquisition, as a combined company we have been and will continue to be required to devote significant management attention and resources to integrating the business practices and operations of the two businesses. As a combined company, we may fail to realize some or all of the anticipated benefits of the acquisition if the integration process takes longer than expected or is more costly than expected. As a combined company we may encounter difficulties in the integration process that include the following:

•	the inability to successfully combine the businesses of Castlight and Jiff in a manner that permits the combined company to achieve the synergies anticipated to result from the acquisition, which would result in the anticipated benefits of the acquisition not being realized partly or wholly in the time frame currently anticipated or at all;	
		
•	lost sales and customers as a result of certain customers of either of the two companies deciding not to do business with the combined company;	
		
•	complexities associated with managing the combined businesses;	
		
•	creating uniform standards, controls, procedures, policies and information systems;	
		
•	performance shortfalls at one or both of the two companies as a result of the diversion of management’s attention caused by integrating the companies’ operations and functionality, or developing new functionality; and	
		
•	potential loss of brand awareness or confusion as a result of our re-branding activities.	

It is possible that the integration process could result in the diversion of management’s attention, the disruption or interruption of, or the loss of momentum in, the ongoing business or inconsistencies in standards, controls, procedures and policies, any of which could adversely affect our ability as a combined company to maintain relationships with customers, partners and employees or its ability to achieve the anticipated benefits of the acquisition, or could reduce the earnings or otherwise adversely affect the business and financial results of the combined company. Moreover, in addition to the possible failure to realize the anticipated benefits of any acquisition, including revenues or return on investment assumptions, we may be exposed to unknown liabilities or impairment charges as a result of such acquisitions.

The market for our offering is immature and volatile, and if it does not further develop, if it develops more slowly than we expect, or if our offering does not drive employee engagement, the growth of our business will be harmed.
Our market is immature and volatile, and it is uncertain whether we will achieve and sustain high levels of demand and market adoption. Our success depends to a substantial extent on the willingness of employers to increase their use of our health benefits platform, the ability of our products to increase employee engagement, as well as on our ability to demonstrate the value of our offering to customers and their employees and to develop new products that provide value to customers and users. If employers do not perceive the benefits of our offering or our offering does not drive employee engagement, then our market might develop more slowly than we expect, or even shrink, which could significantly adversely affect our operating results. In addition, we have limited insight into trends that might develop and affect our business. We might make errors in predicting and reacting to relevant business, legal and regulatory trends, which could harm our business. If any of these events occur, it could materially adversely affect our business, financial condition or results of operations.

In addition, we have devoted substantial efforts to our acquisition of Jiff, and expect to continue to devote substantial efforts to the operation and integration of the Jiff business. We have undertaken these efforts based on our belief that our

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customers are interested in a combined suite of offerings that address both health care management and wellness needs. However, if customer demand for a combined suite of offerings is lower than expected, or takes longer than we expect to develop, then our business will be harmed and our operating results will suffer.
Our quarterly results may fluctuate significantly, which could adversely impact the value of our Class B common stock.
Our quarterly results of operations, including our revenue, gross margin, net loss and cash flows, may vary significantly in the future, and period-to-period comparisons of our operating results may not be meaningful. Accordingly, our quarterly results should not be relied upon as an indication of future performance. Our quarterly financial results may fluctuate as a result of a variety of factors, many of which are outside of our control, including, without limitation, those listed elsewhere in this “Risk Factors” section and those listed below:

•	the addition or loss of large customers, including through acquisitions or consolidations of such customers;	
		
•	seasonal and other variations in the timing of the sales of our offering, as a significantly higher proportion of our customers either enter into new subscription agreements or renew previous agreements with us in the second half of the year.	
		
•	the timing of recognition of revenue, including possible delays in the recognition of revenue due to lengthy and sometimes unpredictable implementation timelines or changes brought about by new accounting pronouncements;	
		
•	failure to meet our contractual commitments under service-level agreements with our customers;	
		
•	the amount and timing of operating expenses related to the maintenance and expansion of our business, operations and infrastructure;	
		
•	our access to pricing and claims data managed by health plans and other third parties, or changes to the fees we pay for that data;	
		
•	the timing and success of introductions of new products, services and pricing by us or our competitors or any other change in the competitive dynamics of our industry, including consolidation among competitors, customers or strategic partners;	
		
•	our ability to attract new customers;	
		
•	customer renewal rates and the timing and terms of customer renewals;	
		
•	network outages or security breaches;	
		
•	the mix of products and services sold or renewed during a period;	
		
•	general economic, industry and market conditions;	
		
•	the timing of expenses related to the development or acquisition of technologies or businesses and potential future charges for impairment of goodwill from acquired companies; and	
		
•	other impacts of new accounting pronouncements.	

We are particularly subject to fluctuations in our quarterly results of operations since the costs associated with entering into customer agreements and implementing our offerings are generally incurred prior to launch, while we generally recognize revenue over the term of the agreement beginning at launch. In addition, some of our contracts with customers provide for one-time bonus payments, or in some cases fee reductions, if our offering does, or does not, achieve certain metrics, such as a certain rate of employee engagement These bonuses or reductions may lead to additional fluctuations in our quarterly operating results. In certain contracts, employee engagement may refer to the number of first time registrations by employees of our customers and in other cases it may refer to return usage of our products by employees. Any fluctuations in our quarterly results may not accurately reflect the underlying performance of our business and could cause a decline in the trading price of our Class B common stock.
We incur significant upfront costs in our customer relationships, and if we are unable to maintain and grow these customer relationships over time, we are likely to fail to recover these costs and our operating results will suffer.
We devote significant resources and incur significant upfront costs to establish relationships with our customers and implement our offering and related services, particularly in the case of large enterprises that often request or require specific features or functions unique to their particular business processes. Accordingly, our operating results will depend in substantial part on our ability to deliver a successful customer experience and persuade our customers to maintain and grow their relationship with us over time. For example, if we are not successful in implementing our offering or delivering a successful customer experience, a customer could terminate or fail to renew their agreement with us, we would lose or be unable to recoup the significant upfront costs that we had expended on such customer and our operating results would suffer. As we grow, our

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customer acquisition costs could outpace our build-up of recurring revenue, and we may be unable to reduce our total operating costs through economies of scale such that we are unable to achieve profitability.
Our ability to deliver our full offering to customers depends in substantial part on our ability to access data and other resources that are managed by a limited number of health plans and other third parties.
In order to deliver the full functionality offered by our health benefits platform, we need continued access, on behalf of our customers, to sources of pricing and claims data, much of which is managed by a limited number of health plans and other third parties. We have developed various long-term and short-term processes to obtain data from certain health plans and other third parties. We are limited in our ability to offer the full functionality of our offering to customers of health plans with whom we do not have a data-sharing or joint customer support process or arrangement.

The terms of the arrangements under which we have access to data managed by health plans and other third parties vary, which can impact the offering we are able to deliver. Many of our arrangements with health plans and third parties have terms that limit our access to and permitted uses of claims or pricing data to the data associated with our mutual customers. Also, some agreements, processes, or arrangements may be terminated if the underlying customer contracts do not continue, or may otherwise be subject to termination or non-renewal in whole or in part.
    In addition, in order to deliver current and potential future functionality of our full health navigation platform, including third-party integrated services, we need access to other resources and services that are largely or fully controlled by third-party integration partners. While we have developed and expect to continue to develop relationships with third parties in order to allow us and our customers to access these resources and services, we are exposed to the risk that third parties may limit or eliminate our access, which would hinder our ability to provide certain integrated health navigation functionality to our customers and harm our business.
The health plans and other third parties that we currently work with may, in the future, change their position and limit or eliminate our access to data and resources, increase the costs for access, provide data and resources to us in more limited or less useful formats, or restrict our permitted uses of data and resources. Furthermore, some health plans and third parties that we rely on to supply data and resources have developed or are developing their own proprietary products and services that may compete with aspects of our platform, and so may perceive continued cooperation with us as a competitive disadvantage and choose to limit or discontinue our access to these data and resources. Failure to continue to maintain and expand our access to suitable pricing and other data and resources may adversely impact our ability to continue to serve existing customers and expand our offering to new customers.
If our access to the data and resources necessary to deliver health navigation functionality is eliminated, reduced or becomes more costly to us, our ability to compete in the marketplace or to grow our revenue could be impaired and our operating results would suffer.
A significant portion of our revenue comes from a limited number of customers, the loss of which would adversely affect our financial results.
Historically, we have relied on a limited number of customers for a substantial portion of our total revenue. For the year ended December 31, 2017, our top 10 customers by revenue accounted for approximately 33% of our total revenue. We rely on our reputation and recommendations from key customers in order to promote our offering to potential customers. The loss of any of our key customers, or a failure of some of them to renew or expand user subscriptions, could have a significant impact on the growth rate of our revenue, reputation and our ability to obtain new customers. In addition, mergers and acquisitions involving our customers could lead to cancellation or non-renewal of our agreements with those customers or by the acquiring or combining companies, thereby reducing the number of our existing and potential customers.

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Because we generally bill our customers and recognize revenue over the term of the contract, near term declines in new or renewed agreements may not be reflected immediately in our operating results and may be difficult to discern.
Most of our revenue in each quarter is derived from agreements entered into with our customers during previous quarters. Consequently, a decline in new or renewed agreements in any one quarter may not be fully reflected in our revenue for that quarter. Such declines, however, would negatively affect our revenue in future periods and the effect of significant downturns in sales of and market demand for our offering, and potential changes in our rate of renewals or renewal terms, may not be fully reflected in our results of operations until future periods. Accordingly, management measures sales performance and forecasts future subscription revenue based on signed annual recurring revenue, or ARR. ARR is a forward-looking metric based on contractual terms in existence as of the end of a reporting period and is subject to change resulting from a number of factors including, but not limited to, addition of new customers, changes in user counts, terminations or non-renewals, as well as upsells and cross-sells. For all of these reasons, the amount of subscription revenue we actually recognize may be different from ARR at the end of a period in which it was recorded. In addition, we may be unable to adjust our cost structure rapidly, or at all, to take account of reduced revenue. Our subscription model also makes it difficult for us to rapidly increase our total revenue through additional sales in any period, as revenue from new customers must be recognized over the applicable term of the agreement. Accordingly, the effect of changes in the industry impacting our business or changes we experience in our new sales may not be reflected in our short-term results of operations.

Our sales and implementation cycle can be long and unpredictable and require considerable time and expense, which may cause our operating results to fluctuate.
The sales cycle for our health benefits platform, from initial contact with a potential lead to contract execution and implementation, varies widely by customer, ranging from three to 24 months. Some of our customers undertake a significant and prolonged evaluation process, including whether our offering meets a customer’s unique benefits program needs, that frequently involves not only the review of our offering but also of our competitors, which has in the past resulted in extended sales cycles. Our sales efforts involve educating our customers about the use, technical capabilities and benefits of our offering. Moreover, our large enterprise customers often begin to deploy our service on a limited basis, but nevertheless demand extensive configuration, integration services and pricing concessions, which increase our upfront investment in the sales effort with no guarantee that these customers will deploy our offering widely enough across their organization to justify our substantial upfront investment. It is possible that in the future we may experience even longer sales cycles, more complex customer needs, higher upfront sales costs and less predictability in completing some of our sales. In addition, even after contracts are signed, our implementation timelines can delay recognition of related revenue for several periods. If our sales cycle lengthens or our substantial upfront sales and implementation investments do not result in sufficient sales or revenue to justify our investments, our operating results may be harmed.
The health care industry is heavily regulated. Our failure to comply with regulatory requirements could create liability for us, result in adverse publicity and otherwise negatively affect our business.
The health care and wellness industries are heavily regulated and constantly evolving due to the changing political, legislative and regulatory landscape and other factors. Many health care and wellness laws are complex, and their application to specific services and relationships may not be clear. Further, some health care laws differ from state to state and it is difficult to ensure our business complies with evolving laws in all states. Our operations may be adversely affected by enforcement initiatives. By offering partner applications we may become subject to additional regulations that don’t ordinarily apply to our own core business. Our failure to accurately anticipate the application of these laws and regulations to our business, or any other failure to comply with regulatory requirements, could create liability for us, result in adverse publicity and negatively affect our business. For example, failure to comply with these requirements could result in the unwillingness of current and potential customers to work with us. Federal and state legislatures and agencies periodically consider proposals to revise aspects of the legal rules applicable to the health care industry, or to revise or create additional statutory and regulatory requirements. Such proposals, if implemented, could impact our operations, the use of our offering and our ability to market new products and services, or could create unexpected liabilities for us. We cannot predict what changes to laws or regulations might be made in the future or how those changes could affect our business or our operating costs.
If we fail to comply with applicable health information privacy and security laws and other applicable state, federal and international privacy and security laws, we may be subject to significant liabilities, reputational harm and other negative consequences, including decreasing the willingness of current and potential customers to work with us.

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We are subject to data privacy and security regulation within the jurisdictions where our users reside; these regulations address matters central to our business, including privacy and data protection, personal information, content, data security, data retention and deletion, and user communications. For example, we are subject to the Health Insurance Portability and Accountability Act of 1996 and its implementing regulations (collectively “HIPAA”), which established uniform federal standards for certain “covered entities,” which include health care providers and health plans, governing the conduct of specified electronic health care transactions and protecting the security and privacy of protected health information (“PHI”). The Health Information Technology for Economic and Clinical Health Act (“HITECH”) which became effective on February 17, 2010, makes HIPAA’s privacy and security standards directly applicable to “business associates,” which are independent contractors or agents of covered entities that create, receive, maintain, or transmit PHI in connection with providing a service for or on behalf of a covered entity. HITECH also increased the civil and criminal penalties that may be imposed against covered entities, business associates and other persons, and gave state attorneys general new authority to file civil actions for damages or injunctions in federal courts to enforce HIPAA’s requirements and seek attorney’s fees and costs associated with pursuing federal civil actions.

A portion of the data that we obtain and handle for or on behalf of our customers is considered PHI, subject to HIPAA as well as other regulations. Under HIPAA and our contractual agreements with our HIPAA covered entity health plan customers, we are considered a “business associate” to those customers, and are required to maintain the privacy and security of PHI in accordance with HIPAA and the terms of our business associate agreements with customers, including by implementing HIPAA-required administrative, technical and physical safeguards. We have incurred, and will continue to incur, significant costs to establish and maintain these safeguards and, if additional safeguards are required to comply with HIPAA regulations or our customers’ requirements, our costs could increase further, which would negatively affect our operating results. Furthermore, if we fail to maintain adequate safeguards, or we or our agents and subcontractors use or disclose PHI in a manner prohibited or not permitted by HIPAA or our business associate agreements with our customers, or if the privacy or security of PHI that we obtain and handle is otherwise compromised, we could be subject to significant liabilities and consequences, including, without limitation:

•	breach of our contractual obligations to customers, which may cause our customers to terminate their relationship with us and may result in potentially significant financial obligations to our customers;	
		
•	investigation by regulatory authorities empowered to enforce HIPAA and other applicable regulations, including but not limited to the U.S. Department of Health and Human Services and state attorneys general, and the possible imposition of civil penalties;	
		
•	private litigation by individuals adversely affected by any violation of HIPAA, HITECH or comparable laws for which we are responsible; and	
		
•	negative publicity, which may decrease the willingness of current and potential future customers to work with us and negatively affect our sales and operating results.	
We also have ongoing compliance obligations with respect to applicable portions of the EU General Data Protection Regulation, which became effective on May 25, 2018, which we have to comply with to the extent we have applicable users in the European Union, and we cannot assure you that our compliance efforts will be effective. The introduction of new products or expansion of our activities may subject us to additional laws and regulations. We have incurred, and will continue to incur, significant costs to establish and maintain compliance with new regulations that may apply to us, which would negatively affect our operating results.
Further, we publish statements to end users of our services that describe how we handle and protect personal information. If federal or state regulatory authorities or private litigants consider any portion of these statements to be untrue, we may be subject to claims of deceptive practices, which could lead to significant liabilities and consequences, including, without limitation, costs of responding to investigations, defending against litigation, settling claims and complying with regulatory or court orders.
We also send SMS text messages to potential end users who are eligible to use our service through certain customers and partners. While we get consent from or on behalf of these individuals to send text messages, federal or state regulatory authorities or private litigants may claim that the notices and disclosures we provide, form of consents we obtain or our SMS texting practices are not adequate. These SMS texting campaigns are potential sources of risk for class action lawsuits and liability for our company. Numerous class-action suits under federal and state laws have been filed in recent years against companies who conduct SMS texting programs. Many of those suits have resulted in multi-million dollar settlements to the plaintiffs.

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Our growth depends in part on the success of our strategic relationships with third parties.
In order to grow our business, we anticipate that we will continue to depend on our relationships with third parties, including Anthem, Inc. We have continued to expand our ongoing relationship with Anthem, including Anthem’s offering of Engage, a Castlight-powered health navigation platform, and our development and support of the base technology underlying Anthem’s core care guidance offering. Apart from channel partners and data partners, our offering also includes the integration of products supplied by strategic partners, who offer complementary products and services. We rely on these strategic partners in the timely and successful deployment of our offering to our customers. If the products provided by these partners have defects or do not operate as expected, if the services provided by these partners are not completed in a timely manner, if our partners have organizational or supply issues, or if we do not effectively integrate and support products supplied by these strategic partners, then we may have difficulty with the deployment of our offering that may result in loss of, or delay in, revenues, increased service and support costs and a diversion of development resources. We also may compete in some areas with these same partners. If these strategic partners fail to perform or choose not to cooperate with us on certain projects, in addition to the effects described above, we could experience loss of customers and market share; and failure to attract new customers or achieve market acceptance for our products. Identifying partners, negotiating and documenting relationships and building integrations with them, requires significant time and resources. If we are unsuccessful in establishing or maintaining our relationships with Anthem, other third parties, our ability to compete in the marketplace or to grow our revenue could be impaired and our operating results may suffer. Even if we are successful, we cannot assure you that these relationships will result in increased customer use of our platform or increased revenue.

Shifts in health care benefits trends, including any potential decline in the number of self-insured employers, or the emergence of new technologies may render our offering obsolete or require us to expend significant resources in order to remain competitive.
The U.S. health care industry is massive, with a number of large market participants with conflicting agendas, is subject to significant government regulation and is currently undergoing significant change. Changes in our industry, for example, towards private health care exchanges or away from high deductible health plans, or the emergence of new technologies as more competitors enter our market, could result in our offering being less desirable or relevant.

For example, we currently derive substantially all of our revenue from customers that are self-insured employers. The demand for significant portions of our offering depends on the need of self-insured employers to manage the costs of health care services that they pay on behalf of their employees. While the percentage of employers who are self-insured has been increasing over the past decade, there is no assurance that this trend will continue. Various factors, including changes in the health care insurance market or in government regulation of the health care industry, could cause the percentage of self-insured employers to decline, which would adversely affect the market for our offering and would negatively affect our business and operating results. Furthermore, such trends and our business could be affected by changes in health care spending resulting from changes in the law like we saw with the Patient Protection and Affordable Care Act (the “ACA”). Under the ACA, the federal government and several state governments established public exchanges in which consumers can purchase health insurance. In the event that the ACA, any amendment or repeal of the ACA, or other changes to the legal landscape causes our customers to change their health care benefits plans or move to use of exchanges such that it reduces the need for our offering, or if the number of self-insured employers otherwise declines, we would be forced to compete on additional product and service attributes or to expend significant resources in order to alter our offering to remain competitive.
    
If health care benefits trends shift or entirely new technologies, services or programs are developed that replace or disrupt existing offerings, our existing or future offerings could be rendered obsolete and our business could be adversely affected. In addition, we may experience difficulties with software development, industry standards, design or marketing that could delay or prevent our development, introduction or implementation of new products and enhancements.
We may require additional capital to support business growth, and this capital might not be available to us on acceptable terms or at all.

Our operations have consumed substantial amounts of cash since inception and we intend to continue to make significant investments to support our business growth, respond to business challenges or opportunities, develop new products and services, enhance our existing offering and services, enhance our operating infrastructure and potentially acquire complementary businesses and technologies. For the  six months ended  June 30, 2018 and 2017, our net cash used in operating activities was  $20.1 million and $15.0 million , respectively. Our future capital requirements may be significantly different from our current estimates and will depend on many factors including our growth rate, new customer acquisitions, subscription

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renewal activity, operation and integration of the Jiff business, the timing and extent of spending to support development efforts, the expansion of sales and marketing activities, the introduction of new and enhanced services offerings and the continuing market acceptance of our cloud-based subscription services. Accordingly, we might need to engage in equity or debt financings or collaborative arrangements to secure additional funds. If we raise additional funds through further issuances of equity or convertible debt securities, our existing stockholders could suffer significant dilution, and any new equity securities we issue could have rights, preferences and privileges superior to those of holders of our Class B common stock. Any debt financing secured by us in the future could involve restrictive covenants relating to our capital-raising activities and other financial and operational matters, which might make it more difficult for us to obtain additional capital and to pursue business opportunities, including potential acquisitions. We might have to obtain funds through arrangements with collaborative partners or others that may require us to relinquish rights to our technologies or offering that we otherwise would not relinquish. In addition, it may be difficult to obtain financing in the public markets or to obtain debt financing, and we might not be able to obtain additional financing on commercially reasonable terms, if at all. If we are unable to obtain adequate financing or financing on terms satisfactory to us when we require it, our ability to continue to support our business growth and to respond to business challenges could be significantly limited.
We depend on data centers operated by third parties for our offering, and any disruption in the operation of these facilities could adversely affect our business.
We provide our Castlight health benefits platform through computer hardware that is currently located in two geographically-dispersed third-party data centers in the U.S., each of which are operated by the same IT hosting company. Our Wellbeing services are hosted on Amazon Web Services hardware through virtual private clouds. Primary hosting is located at the U.S.-West availability zone in Oregon with disaster recovery/business continuity plan hosting located at the U.S.-East availability zone in Virginia. While we control and have access to our owned servers and all of the components of our network that are located in these external data centers, we do not control the operation of these facilities. The owners of our data centers and hosting services have no obligation to renew the agreements with us on commercially reasonable terms, or at all. If we are unable to renew these types of agreements on commercially reasonable terms, or if our data center operators and hosting services are acquired or cease operations, we may be required to transfer our servers and other infrastructure to new data center facilities or hosting services, and we may incur significant costs and possible service interruption in connection with doing so.

Problems faced by our third-party data center and hosting locations could adversely affect the experience of our customers. The operators of the data centers and hosting services could decide to close the facilities or change and suspend their service offerings without adequate notice. In addition, any financial difficulties, such as bankruptcy, faced by the operators of the data centers or any of the service providers with whom we or they contract may have negative effects on our business, the nature and extent of which are difficult to predict. Additionally, if our data centers and hosting facilities are unable to keep up with our growing needs for capacity, this could have an adverse effect on our business. For example, a rapid expansion of our business could affect the service levels at our data centers and hosting locations or cause such data centers and systems to fail. Any changes in third-party service levels at our data centers and hosting locations or any disruptions or other performance problems with our product offering could adversely affect our reputation and may damage our customers’ stored files or result in lengthy interruptions in our services. Interruptions in our services might reduce our revenue, increase our costs associated with remediation or cause us to issue refunds to customers for prepaid and unused subscriptions, subject us to potential liability or adversely affect our renewal rates
The information that we provide to our customers, and their employees and families, could be inaccurate or incomplete, which could harm our business, financial condition and results of operations.
We provide price, quality and other health care-related information for use by our customers, and their employees and families, to search and compare options for health care services. Third-party health plans and our customers provide us with most of these data. Because data in the health care industry is fragmented in origin, inconsistent in format and often incomplete, the overall quality of data in the health care industry is poor, and we frequently discover data issues and errors. If the data that we provide to our customers are incorrect or incomplete or if we make mistakes in the capture or input of these data, our reputation may suffer and our ability to attract and retain customers may be harmed.
    
In addition, a court or government agency may take the position that our storage and display of health information exposes us to personal injury liability or other liability for wrongful delivery or handling of health care services or erroneous health information. While we maintain insurance coverage, this coverage may prove to be inadequate or could cease to be available to us on acceptable terms, if at all. Even unsuccessful claims could result in substantial costs, harm to our reputation

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and diversion of management resources. A claim brought against us that is uninsured or under-insured could harm our business, financial condition and results of operations.

If we cannot maintain our corporate culture as we grow, we could lose the elements of our culture that we believe contribute to our success and our business may be harmed.
We believe that a critical asset for our business, and a source of our competitive strength, is our unique company culture, which we believe fosters a high level of cross-functional collaboration and desire for excellence in our performance and product. As we grow and change, we may find it difficult to maintain these important aspects of our corporate culture. Our acquisition of Jiff, and the further integration of Jiff’s business and personnel into our company, may present additional challenges to our ability to maintain our corporate culture. Any failure to preserve our culture could also negatively affect our ability to attract and retain personnel, our reputation and our ability to continue to build and advance our offering and may otherwise adversely affect our future success.
If we fail to develop widespread brand awareness cost-effectively, our business may suffer.
We believe that developing and maintaining widespread awareness of our brand in a cost-effective manner is critical to achieving widespread adoption of our offering and attracting new customers. Brand promotion activities may not generate customer awareness or increase revenue, and even if they do, any increase in revenue may not offset the expenses we incur in building our brand. If we fail to successfully promote and maintain our brand, or incur substantial expenses, we may fail to attract or retain customers necessary to realize a sufficient return on our brand-building efforts, or to achieve the widespread brand awareness that is critical for broad customer adoption of our offering.
Any failure to protect our intellectual property rights could impair our ability to protect our proprietary technology and our brand.
Our success depends in part on our ability to enforce our intellectual property and other proprietary rights. We rely upon a combination of patent, trademark, copyright and trade secret laws, as well as license and access agreements and other contractual provisions, to protect our intellectual property and other proprietary rights. In addition, we attempt to protect our intellectual property and proprietary information by requiring certain of our employees, consultants and contractors to enter into confidentiality, noncompetition and assignment of inventions agreements. These laws, procedures and restrictions provide only limited protection and any of our intellectual property rights may be challenged, invalidated, circumvented, infringed or misappropriated. While we have three U.S. patent applications pending, and we currently have one issued U.S. patent, we cannot ensure that any of our pending patent applications will be granted or that our issued patent will adequately protect our intellectual property. In addition, if any patents are issued in the future, they may not provide us with any competitive advantages, or may be successfully challenged by third parties. To the extent that our intellectual property and other proprietary rights are not adequately protected, third parties might gain access to our proprietary information, develop and market solutions similar to ours, or use trademarks similar to ours, each of which could materially harm our business. Further, unauthorized parties may attempt to copy or obtain and use our technology to develop products with the same functionality as our offering, and policing unauthorized use of our technology and intellectual property rights is difficult and may not be effective. The failure to adequately protect our intellectual property and other proprietary rights could materially harm our business.
We could incur substantial costs as a result of any claim of infringement of another party’s intellectual property rights.
In recent years, there has been significant litigation in the United States involving patents and other intellectual property rights. Companies in the Internet and technology industries are increasingly bringing and becoming subject to suits alleging infringement of proprietary rights, particularly patent rights, and our competitors and other third parties may hold patents or have pending patent applications, which could be related to our business. These risks have been amplified by the increase in third parties, which we refer to as non-practicing entities, whose sole or primary business is to assert such claims. We expect that we may receive in the future notices that claim we or our customers using our offering have misappropriated or misused other parties’ intellectual property rights, particularly as the number of competitors in our market grows and the functionality of products amongst competitors overlaps. If we are sued by a third party that claims that our technology infringes its rights, the litigation, whether or not successful, could be extremely costly to defend, divert our management’s time, attention and resources, damage our reputation and brand and substantially harm our business. We do not currently have an extensive patent portfolio of our own, which may limit the defenses available to us in any such litigation.

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In addition, in most instances, we have agreed to indemnify our customers against certain third-party claims, which may include claims that our offering infringes the intellectual property rights of such third parties. Our business could be adversely affected by any significant disputes between us and our customers as to the applicability or scope of our indemnification obligations to them. The results of any intellectual property litigation to which we might become a party, or for which we are required to provide indemnification, may require us to do one or more of the following:
		
•	cease offering or using technologies that incorporate the challenged intellectual property;	
		
•	make substantial payments for legal fees, settlement payments or other costs or damages;	
		
•	obtain a license, which may not be available on reasonable terms, to sell or use the relevant technology; or	
		
•	incur substantial costs and reallocate resources to redesign our technology to avoid infringement.	

If we are required to make substantial payments or undertake any of the other actions noted above as a result of any intellectual property infringement claims against us or any obligation to indemnify our customers for such claims, such payments or costs could have a material adverse effect upon our business and financial results.
Our use of open source technology could impose limitations on our ability to commercialize our software platform.
Our offering incorporates open source software components that are licensed to us under various public domain licenses. Some open source software licenses require users who distribute open source software as part of their software to publicly disclose all or part of the source code to such software or make available any derivative works of the open source code on unfavorable terms or at no cost. There is little or no legal precedent governing the interpretation of many of the terms of these licenses and therefore the potential impact of such terms on our business is somewhat unknown. There is a risk that such licenses could be construed in a manner that imposes unanticipated conditions or restrictions on our ability to market our software platform. While we monitor our use of open source software and try to ensure that none is used in a manner that would require us to disclose our source code or that would otherwise breach the terms of an open source agreement, such use could inadvertently occur and we may be required to release our proprietary source code, pay damages for breach of contract, re-engineer our offering, discontinue sales of our offering in the event re-engineering cannot be accomplished on a timely basis or take other remedial action that may divert resources away from our development efforts, any of which could cause us to breach customer contracts, harm our reputation, result in customer losses or claims, increase our costs or otherwise adversely affect our business and operating results.

We may face risks related to securities litigation that could result in significant legal expenses and settlement or damage awards.

We have been in the past and may in the future become subject to claims and litigation alleging violations of the securities laws or other related claims, which could harm our business and require us to incur significant costs. For example, during the second quarter of 2015, four purported securities class action lawsuits, which were later consolidated into a single action, were filed in the Superior Court of the State of California, County of San Mateo, against the Company, certain of its current and former directors, executive officers, significant stockholders and underwriters associated with its initial public offering (“IPO”). The lawsuits were brought by purported stockholders of the Company seeking to represent a class consisting of all those who purchased the Company’s stock pursuant or traceable to the Registration Statement and Prospectus issued in connection with its IPO, alleging claims under Sections 11, 12(a)(2) and 15 of the Securities Act of 1933. We are generally obliged, to the extent permitted by law, to indemnify our current and former directors and officers who are named as defendants in these types of lawsuits. On March 28, 2016, the parties to the consolidated actions reached a mutually acceptable resolution by way of a mediated cash settlement for an aggregate amount of $9.5 million and the Court entered final approval of the settlement on October 28, 2016. As a result of the settlement Castlight recorded a net charge of $2.9 million to general and administrative expense in 2016. This amount represents the portion of settlement that was not covered by insurance and legal fees incurred in 2016 regarding this matter. Future litigation may require significant attention from management and could result in significant legal expenses, settlement costs or damage awards that could have a material impact on our financial position, results of operations and cash flows.
The development and expansion of our business through acquisitions of other companies or technologies or other strategic transactions could divert our management’s attention, result in dilution to our stockholders and otherwise disrupt our operations and adversely affect our operating results.
On April 3, 2017, we completed our acquisition of Jiff, and issued approximately 27 million shares and options to former Jiff equity holders, representing approximately 20% of the combined company on a fully-diluted basis. The process of

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integrating the Jiff business, team and technology has created, and will continue to create, unforeseen operating difficulties and expenditure requirements. We may not be able to effectively manage the combined Castlight and Jiff business, or effectively integrate the personnel, operations and technologies of Jiff.
In addition, in 2015, we made a preferred stock investment in Lyra Health of $4.1 million, associated with a strategic alliance with Lyra Health, which we subsequently divested in 2017. In May 2016, we also sold and issued to SAP Technologies, Inc., or SAP, approximately 4.7 million shares of our Class B Common Stock and a warrant to purchase up to approximately 1.9 million shares of our Class B Common Stock. The warrant expired on its terms without becoming exercisable as we did not enter into an alliance agreement with SAP related to the distribution and the reselling of our solutions by November 17, 2017.
As we have done in the past, we may in the future seek to acquire or invest in businesses, products and services or technologies or enter into other strategic transactions that we believe could complement or expand our offering, enhance our technical capabilities or otherwise offer growth opportunities. We have limited experience in acquiring other businesses and entering into strategic transactions. We may not achieve any of the anticipated benefits of any of these strategic transactions. The pursuit of potential acquisitions and other strategic transactions may divert the attention of management and cause us to incur various expenses in identifying, investigating and pursuing suitable acquisitions and strategic alliances or transactions, whether or not they are consummated. We may not achieve any of the anticipated benefits or stated objectives from these or other strategic transactions we may enter into in the future.
    
Factors affecting our ability to achieve the benefits of the Jiff acquisition, other acquisitions or other strategic alliances     could include:

•	inability to integrate or benefit from acquired technologies or services or strategic collaborations or alliances in an efficient, effective or profitable manner;	
		
•	unanticipated costs or liabilities associated with the acquisition or strategic transaction;	
		
•	challenges in achieving strategic objectives, cost savings and other benefits expected from such transactions;	
		
•	the lack of unilateral control over a strategic alliance and the risk that strategic partners have business goals and interests that are not aligned with ours;	
		
•	delays, difficulties or unexpected costs in the integration, assimilation, implementation or modification of platforms, systems, functions, technologies and infrastructure to support the combined business or strategic alliance, as well as maintaining and integrating accounting systems and operations, uniform standards, controls (including internal accounting controls), procedures and policies	
		
•	difficulty converting the customers of the acquired business onto our platform and contract terms, including disparities in the revenue, licensing, support or professional services model of the acquired company;	
		
•	diversion of management’s attention from other business concerns;	
		
•	adverse effects to our existing business relationships with business partners and customers as a result of the acquisition or strategic transaction;	
		
•	the potential loss of key employees;	
		
•	the risk that we do not realize a satisfactory return on our investments;	
		
•	use of resources that are needed in other parts of our business; and	
		
•	use of substantial portions of our available cash to consummate the acquisition or strategic transaction.	

In addition, a significant portion of the purchase price of Jiff, and other companies we acquire or invest in, may be allocated to acquired goodwill and other intangible assets, which must be assessed for impairment at least annually. In the future, if our acquisitions do not yield expected returns, we may be required to take charges to our operating results based on this impairment assessment process, which could adversely affect our results of operations.

The acquisition of Jiff resulted, and other acquisitions and strategic transactions could also result, in dilutive issuances of equity securities or the incurrence of debt, which could adversely affect our operating results. In addition, if an acquired business or other strategic transaction fails to meet our expectations, our operating results, business and financial position may suffer.
If we are unable to implement and maintain effective internal control over financial reporting in the future, investors may lose confidence in the accuracy and completeness of our financial reports and the market price of our Class B common stock may be negatively affected.

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As a public company, we are required to maintain internal control over financial reporting and to report any material weaknesses in such internal control. Section 404 of the Sarbanes-Oxley Act of 2002, or the Sarbanes-Oxley Act, requires that we evaluate and determine the effectiveness of our internal control over financial reporting and, provide a management report on the internal control over financial reporting. Our independent registered public accounting firm is not required to audit the effectiveness of our internal control over financial reporting until after we are no longer an “emerging growth company”, as defined in the JOBS Act. At such time, our independent registered public accounting firm may issue a report that is adverse in the event it is not satisfied with the level at which our internal control over financial reporting is documented, designed or operating. If we have a material weakness in our internal control over financial reporting, we may not detect errors on a timely basis and our financial statements may be materially misstated. We are in the process of designing and implementing the internal control over financial reporting required to comply with this obligation, which process will be time consuming, costly and complicated. If we identify material weaknesses in our internal control over financial reporting, if we are unable to comply with the requirements of Section 404 in a timely manner, if we are unable to assert that our internal control over financial reporting is effective, or if our independent registered public accounting firm concludes we have a material weakness in our internal control over financial reporting, investors may lose confidence in the accuracy and completeness of our financial reports, the market price of our Class B common stock could be negatively affected and we could become subject to investigations by the New York Stock Exchange, on which our securities are listed, the SEC or other regulatory authorities, which could require us to obtain additional financial and management resources.
Changes in accounting principles may cause previously unanticipated fluctuations in our financial results, and the implementation of such changes may impact our ability to meet our financial reporting obligations.
We prepare our financial statements in accordance with U.S. GAAP which are subject to interpretation or changes by the Financial Accounting Standards Board, or FASB, the SEC, and other various bodies formed to promulgate and interpret appropriate accounting principles. New accounting pronouncements and changes in accounting principles have occurred in the past and are expected to occur in the future which may have a significant effect on our financial results. For example, effective January 1, 2018, we adopted Accounting Standard Codification Topic 606, Revenue from Contracts with Customers. We adopted the requirements of the new standard utilizing the full retrospective method, which required the Company to recast prior reporting periods. While the adoption of the new standard did not change the cash flows we receive from our contracts with customers, the changes to our reporting practices and the potential fluctuations in our reported revenue could cause a decline and/or fluctuations in the price of our common stock.

The adoption of the new standard significantly impacted our costs to fulfill as well as our costs to obtain contracts with customers. For fulfillment costs, the new standard states that an entity shall recognize an asset from the costs incurred to fulfill a contract if certain criteria are met. Similar to fulfillment costs, for costs to obtain a contract (which are primarily sales commissions and broker fees), the standard states that costs to obtain a contract shall be amortized on a systematic basis that is consistent with the transfer to the customer of the goods or services to which the asset relates. Prior to adoption, we expensed costs to fulfill a contract when they were incurred, capitalized certain sales commissions and amortized those costs over the non-cancelable portion of our subscription contracts. Under the new standard, the amortization period for our costs to obtain a contract could be longer. Additionally, the timing of revenue recognition for certain of our revenue arrangements was impacted by the changes imposed by the new standard. Any difficulties in implementation of changes in accounting standards, including the ability to modify our accounting systems, could cause us to fail to meet our financial reporting obligations, which could result in regulatory discipline and harm investors’ confidence in us.
We incur significantly increased costs and devote substantial management time as a result of operating as a public company.
As a public company, we incur significant legal, accounting and other expenses that we did not incur as a private company. For example, we are subject to the reporting requirements of the Exchange Act and are required to comply with the applicable requirements of the Sarbanes-Oxley Act and the Dodd-Frank Wall Street Reform and Consumer Protection Act, as well as rules and regulations subsequently implemented by the SEC and the New York Stock Exchange, including the establishment and maintenance of effective disclosure and financial controls, changes in corporate governance practices and required filing of annual, quarterly and current reports with respect to our business and operating results. Compliance with these requirements increases our legal and financial compliance costs and makes some activities more time consuming and costly. In addition, our management and other personnel divert attention from operational and other business matters to devote substantial time to these public company requirements. In particular, we incur significant expenses and devote substantial management

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effort toward ensuring compliance with the requirements of Section 404 of the Sarbanes-Oxley Act, which will increase when we are no longer an emerging growth company, as defined by the JOBS Act.

Operating as a public company makes it more expensive for us to obtain director and officer liability insurance, and in the future we may be required to accept reduced coverage or incur substantially higher costs to obtain coverage. This could also make it more difficult for us to attract and retain qualified people to serve on our board of directors, our board committees or as executive officers.
We are an emerging growth company and the reduced disclosure requirements applicable to emerging growth companies may make our Class B common stock less attractive to investors.
We are an emerging growth company, as defined under the JOBS Act. For as long as we continue to be an emerging growth company, we intend to take advantage of certain exemptions from various reporting requirements that are applicable to other public companies including, but not limited to, reduced disclosure obligations regarding executive compensation in our periodic reports and proxy statements and exemptions from the requirements of holding a nonbinding advisory vote on executive compensation and stockholder approval of any golden parachute payments not previously approved. We cannot predict if investors will find our Class B common stock less attractive because we will rely on these exemptions. If some investors find our Class B common stock less attractive as a result, there may be a less active trading market for our Class B common stock and our stock price may be more volatile.

We will remain an emerging growth company until the earliest of (i) the end of the year in which the market value of our Class B common stock that is held by non-affiliates exceeds $700 million as of June 30, (ii) the end of the year in which we have total annual gross revenue of $1 billion or more during such year, (iii) the date on which we issue more than $1 billion in non-convertible debt in a three-year period or (iv) December 31, 2019.
We may not be able to utilize a significant portion of our net operating loss or research tax credit carryforwards, which could adversely affect our profitability.
Our primary tax jurisdiction is the United States. All of our tax years are open to examination by U.S. federal and state tax authorities due to our history of tax losses. We have provided a full valuation allowance for our deferred tax assets due to the uncertainty surrounding the future realization of such assets. Therefore, no benefit has been recognized for the net operating loss carryforwards and other deferred tax assets. The net operating loss could expire unused and be unavailable to reduce future income tax liabilities, which could adversely affect our profitability.
Economic uncertainties or downturns in the general economy or the industries in which our customers operate could disproportionately affect the demand for our offering and negatively impact our results of operations.
General worldwide economic conditions have experienced periods of significant downturn, and market volatility and uncertainty remain widespread, making it extremely difficult for our customers and us to accurately forecast and plan future business activities. For example, in June 2016, the decision by referendum to withdraw the United Kingdom (U.K.) from the European Union caused significant volatility in global stock markets, including those in the U.S., and fluctuations in currency exchange rates. The results of this referendum, or other global events, may continue to create global economic uncertainty not only in the U.K., but in other regions, including where we do business. In addition, these conditions could cause our customers or prospective customers to decrease headcount, benefits or human resources budgets, which could decrease corporate spending on our products and services, resulting in delayed and lengthened sales cycles, a decrease in new customer acquisition and loss of customers. Furthermore, during challenging economic times, our customers may have difficulty gaining timely access to sufficient credit or obtaining credit on reasonable terms, which could impair their ability to make timely payments to us and adversely affect our revenue. If that were to occur, our financial results could be harmed. Further, challenging economic conditions might impair the ability of our customers to pay for the products and services they already have purchased from us and, as a result, our write-offs of accounts receivable could increase. We cannot predict the timing, strength, or duration of any economic slowdown or recovery. If the condition of the general economy or markets in which we operate worsens, our business could be harmed.

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Our estimates of market opportunity and forecasts of market growth may prove to be inaccurate, and even if the market in which we compete achieves the forecasted growth, our business could fail to grow at similar rates, if at all.
Market opportunity estimates and growth forecasts are subject to significant uncertainty and are based on assumptions and estimates that may not prove to be accurate. Our estimates and forecasts relating to the size and expected growth of the market for our products and services may prove to be inaccurate. Even if the market in which we compete meets our size estimates and forecasted growth, our business could fail to grow at similar rates, if at all.
Natural or man-made disasters and other similar events may significantly disrupt our business and negatively impact our results of operations and financial condition.
Our offices may be harmed or rendered inoperable by natural or man-made disasters, including earthquakes, power outages, fires, floods, nuclear disasters and acts of terrorism or other criminal activities, which may render it difficult or impossible for us to operate our business for some period of time. For example, our headquarters is located in the San Francisco Bay Area, a region known for seismic activity. Any disruptions in our operations related to the repair or replacement of our office could negatively impact our business and results of operations and harm our reputation. In addition, we may not carry business insurance sufficient to compensate for losses that may occur. Any such losses or damages could have a material adverse effect on our business, results of operations and financial condition. In addition, the facilities of significant customers, health plans or major strategic partners may be harmed or rendered inoperable by such natural or man-made disasters, which may cause disruptions, difficulties or material adverse effects on our business.
Risks Related to Our Class B Common Stock
The stock price of our Class B common stock may be volatile or may decline regardless of our operating performance.

The market price of our Class B common stock has fluctuated significantly since our initial public offering and may continue to fluctuate. These fluctuations could cause you to lose all or part of your investment in our Class B common stock. Factors, many of which are beyond our control, that could cause additional fluctuations in the market price of our Class B common stock include the following:

•	overall performance of the equity markets;	
		
•	our operating performance and the performance of other similar companies;	
		
•	changes in the estimates of our operating results that we provide to the public or our failure to meet these projections;	
		
•	failure of securities analysts to maintain coverage of us, changes in financial estimates by securities analysts who follow our company or our failure to meet these estimates or the expectations of investors or changes in recommendations by securities analysts that elect to follow our Class B common stock;	
		
•	sales of shares of our Class B common stock by us or our stockholders, including same day sales to cover tax withholdings as a result of settlement of restricted stock units;	
		
•	announcements of technological innovations, new products or enhancements to services, acquisitions, strategic alliances or significant agreements by us or by our competitors;	
		
•	disruptions in our services due to computer hardware, software or network problems;	
		
•	announcements of customer additions and customer cancellations or delays in customer purchases;	
		
•	recruitment or departure of key personnel;	
		
•	the economy as a whole, market conditions in our industry and the industries of our customers;	
		
•	litigation involving us, our industry or both, or investigations by regulators into our operations or those of our competitors;	
		
•	developments or disputes concerning our intellectual property or other proprietary rights;	
		
•	new laws or regulations or new interpretations of existing laws or regulations applicable to our business; and	
		
•	the size of our market float.	
In addition, the stock markets have experienced extreme price and volume fluctuations that have affected and continue to affect the market prices of equity securities of many technology companies. Stock prices of many technology companies have fluctuated in a manner unrelated or disproportionate to the operating performance of those companies. In the past, stockholders have filed securities class action litigation following periods of market volatility. If we were to become involved in new securities litigation, it could subject us to substantial costs, divert resources and the attention of management from our business and adversely affect our business.

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If there are substantial sales of shares of our Class B common stock, the price of our Class B common stock could decline.
The price of our Class B common stock could decline if there are substantial sales of our Class B common stock, particularly sales by our directors, executive officers and significant stockholders, or the perception in the market that the holders of a large number of shares of our Class B common stock intend to sell their shares, and may make it more difficult for stockholders to sell Class B common stock at a time and price that they deem appropriate. We are unable to predict the effect that sales may have on the prevailing market price of our Class B common stock.
In addition, certain of our stockholders have rights, subject to some conditions, to require us to file registration statements covering their shares and to include their shares in registration statements that we may file for ourselves or our stockholders. Registration of the resale of these shares under the Securities Act would generally result in the shares becoming freely tradable without restriction. Any sales of securities by existing stockholders could adversely affect the trading price of our Class B common stock. We also registered shares of Class B common stock that we have issued and may issue under our employee equity incentive and employee stock purchase plans. These shares may be sold freely in the public market upon issuance.
The dual class structure of our Class A and Class B common stock will have the effect of concentrating voting control with our executive officers, directors and their affiliates; this will limit or preclude a stockholder's ability to influence corporate matters.
Each share of Class A common stock and each share of Class B common stock has one vote per share, except on the following matters (in which each share of Class A common stock has ten votes per share and each share of Class B common stock has one vote per share):

•	adoption of a merger or consolidation agreement involving our company;	
		
•	a sale, lease or exchange of all or substantially all of our property and assets;	
		
•	a dissolution or liquidation of our company; or	
		
•	every matter, if and when any individual, entity or “group” (as such term is used in Regulation 13D of the Exchange Act) has, or has publicly disclosed (through a press release or a filing with the SEC) an intent to have, beneficial ownership of 30% or more of the number of outstanding shares of Class A common stock and Class B common stock, combined.	
Because of our dual class common stock structure, the holders of our Class A common stock, who in large part consist of our founders, early investors, directors, executives, employees, will continue to be able to exert significant influence over the corporate matters listed above if any such matter is submitted to our stockholders for approval even if they own less than 50% of the outstanding shares of our Class A and Class B common stock, combined. As of June 30, 2018 , holders of our Class A common stock owned approximately 38% of the outstanding shares of our Class A and Class B common stock, combined, however, holders of our Class A common stock, including our executive officers and directors and their affiliates, have approximately 86% of the voting power of our outstanding capital stock with respect to the matters specified above. This concentrated control by holders of our Class A common stock will limit or preclude the ability of a holder of our Class B common stock to influence those corporate matters for the foreseeable future and, as a result, we may take actions that our stockholders do not view as beneficial. The market price of our Class B common stock could be adversely affected by the structure. In addition, this may prevent or discourage unsolicited acquisition proposals or offers for capital stock that a stockholder may feel are in its best interests.
Transfers by holders of our Class A common stock will generally result in those shares converting to our Class B common stock, subject to limited exceptions, such as certain transfers effected for estate planning purposes. The conversion of our Class A common stock to our Class B common stock will have the effect, over time, of increasing the relative voting power of those holders of Class A common stock who retain their shares in the long term. If, for example, directors and their affiliates retain a significant portion of their holdings of our Class A common stock for an extended period of time, they could continue to significantly influence the combined voting power of our Class A and Class B common stock with respect to each of the matters identified in the list above.

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If securities or industry analysts do not publish research or publish inaccurate or unfavorable research about our business, our stock price and trading volume could decline.
The trading market for our Class B common stock depends in part on the research and reports that securities or industry analysts publish about us or our business. If one or more of the analysts who cover us downgrade our Class B common stock or publish inaccurate or unfavorable research about our business, our Class B common stock price would likely decline. If one or more of these analysts cease coverage of us or fail to publish reports on us regularly, demand for our Class B common stock could decrease, which might cause our Class B common stock price and trading volume to decline.

Anti-takeover provisions under Delaware law and in our restated certificate of incorporation and restated bylaws could make a merger, tender offer, or proxy contest difficult, limit attempts by our stockholders to replace or remove members of our board of directors or current management and depress the trading price of our Class B common stock.
Our status as a Delaware corporation and the anti-takeover provisions of the Delaware General Corporation Law may discourage, delay, or prevent a change in control by prohibiting us from engaging in a business combination with an interested stockholder for a period of three years after the person becomes an interested stockholder, even if a change of control would be beneficial to our existing stockholders.
In addition, our restated certificate of incorporation and restated bylaws contain provisions that may make the acquisition of our company or changes in our board of directors or management more difficult, including the following:
		
•	Our board of directors is classified into three classes of directors with staggered three-year terms and directors are only able to be removed from office for cause, which may delay the replacement of a majority of our board of directors or impede an acquirer from rapidly replacing our existing directors with its own slate of directors.	
		
•	Subject to the rights of the holders of any series of preferred stock to elect directors under specified circumstances, only our board of directors has the right to fill a vacancy created by the expansion of our board of directors or the resignation, death or removal of a director, which prevents stockholders from being able to fill vacancies on our board of directors.	
		
•	Our stockholders may not act by written consent or call special stockholders’ meetings; as a result, a holder, or holders, controlling a majority of our Class A and Class B common stock are not be able to take certain actions other than at annual stockholders’ meetings or special stockholders’ meetings, which special meetings may only be called by the chairman of our board, our chief executive officer, our president, or a majority of our board of directors.	
		
•	Certain litigation against us can only be brought in Delaware.	
		
•	Our restated certificate of incorporation authorizes undesignated preferred stock, the terms of which may be established and shares of which may be issued, by our board of directors without the approval of the holders of Class B common stock, which makes it possible for our board of directors to issue preferred stock with voting or other rights or preferences that could impede the success of any attempt to acquire us.	
		
•	Advance notice procedures and additional disclosure requirements apply for stockholders to nominate candidates for election as directors or to bring matters before a meeting of stockholders, which may discourage or deter a potential acquirer from conducting a solicitation of proxies to elect the acquirer’s own slate of directors or otherwise attempting to obtain control of our company.	
		
•	Our restated certificate of incorporation prohibits cumulative voting in the election of directors, which limits the ability of minority stockholders to elect director candidates.	
		
•	Amendment of the anti-takeover provisions of our restated certificate of incorporation require super majority approval by holders of at least two-thirds of our outstanding Class A and Class B    common stock, combined. and	
		
•	In certain circumstances pertaining to change in control, the sale of all or substantially all of our assets and liquidation matters, and on all matters if and when any individual, entity or group has, or has publicly disclosed an intent to have, beneficial ownership of 30% or more of the number of outstanding shares of our Class A and Class B common stock, combined, holders of our Class A common stock are entitled to ten votes per share and holders of our Class B common stock are entitled to one vote per share. As of June 30, 2018 , holders of our Class A common stock owned approximately 38% and holders of our Class B common stock owned approximately 62% of the outstanding shares of our Class A and Class B common stock, combined. However, because of our dual class common stock structure these holders of our Class A common stock have approximately 86% and holders of our Class B common stock have approximately 14% of the total votes with respect to the matters specified above. In all other circumstances, holders of our Class A and Class B common stock are each entitled to one vote per share, and in these other circumstances the holders of our Class A common stock have approximately 38% and holders of our Class B common stock have approximately 62% of the total votes.	

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Item 6. Exhibits
(a) Exhibits.
The Exhibits listed below are filed as part of this Form 10-Q

													
 	 	 	 	Incorporate by Reference	 	 	
Exhibit
Number	 	Description of Document	 	Form	 	File
No.	 	Filing Date	 	Exhibit	 	Filed
Herewith	
 	 	 	 	 	 	 	 	 	 	 	 	 	
10.17**	 	Amendment to Offer Letter between the Registrant and Robert Derek Newell, dated June 11, 2018	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
31.1	 	Certification of Principal Executive Officer Required Under Rule 13a-14(a) and 15d-14(a) of the Securities Exchange Act of 1934, as amended.	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
31.2	 	Certification of Principal Financial Officer Required Under Rule 13a-14(a) and 15d-14(a) of the Securities Exchange Act of 1934, as amended.	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
32.1*	 	Certification of Chief Executive Officer Required Under Rule 13a-14(b) of the Securities Exchange Act of 1934, as amended, and 18 U.S.C. §1350.	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
32.2*	 	Certification of Chief Financial Officer Required Under Rule 13a-14(b) of the Securities Exchange Act of 1934, as amended, and 18 U.S.C. §1350.	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
101.INS	 	XBRL Instance Document	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
101.SCH	 	XBRL Taxonomy Schema Linkbase Document	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
101.CAL	 	XBRL Taxonomy Calculation Linkbase Document	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
101.DEF	 	XBRL Taxonomy Definition Linkbase Document	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
101.LAB	 	XBRL Taxonomy Labels Linkbase Document	 	 	 	 	 	 	 	 	 	X	
 	 	 	 	 	 	 	 	 	 	 	 	 	
101.PRE	 	XBRL Taxonomy Presentation Linkbase Document	 	 	 	 	 	 	 	 	 	X	
_______________________

		
*	The certifications on Exhibit 32 hereto are deemed not “filed” for purposes of Section 18 of the Securities and Exchange Act of 1934, as amended, or otherwise subject to the liability of that Section. Such certifications will not be deemed incorporated by reference into any filing under the Securities Act or the Exchange Act.	
**	Indicates a management contract, compensatory plan or arrangement.	

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SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Company has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

	
					
 	 	CASTLIGHT HEALTH, INC.	
Date:	August 1, 2018	By:	 	/s/ Siobhan Nolan Mangini	
 	 	 	 	Siobhan Nolan Mangini	
 	 	 	 	Chief Financial Officer (Principal Financial Officer)	

56

J UNE 11, 2018

Robert Derek Newell
[Personal address]

Re: Amendment to Offer Letter

Dear Derek,

This letter (this “ Amendment ”) serves to amend the Offer Letter between you and Castlight Health, Inc. (the “ Company ”) dated January 3, 2017 (your “ Offer Letter ”), effective as of the date set forth above. Capitalized terms used in this Amendment that are not otherwise defined herein shall have the meanings ascribed to them in that certain Executive Severance Agreement by and between you and the Company dated as of January 4, 2017 (the “ Executive Severance Agreement ”).

1.	Continued Employment. From the Effective Date through the Separation Date (defined below) (the “ Employment Period ”), you will be employed by the Company as an Advisor to the Chief Executive Officer of the Company, reporting to the Chief Executive Officer. You will provide transition services as may be assigned to you in writing by the Chief Executive Officer.	

2.	Salary and Benefits Continuation. During the Employment Period, you will continue to be paid your base salary at the rate in effect on the date of this Amendment and be eligible for employee benefit plans as set forth in your Offer Letter. Your bonus for the first half of fiscal year 2017 will be paid consistent with standard Company practices, at a rate based on the greater of (i) the standard rate applied to the senior leadership team or (ii) the amount paid to the Company’s Chief Executive Officer. Notwithstanding the foregoing, Section 5 (Compensation Equivalency) in your Offer Letter shall cease to apply.	

3.	Separation Date. Provided that you continue to perform your obligations under (i) the Non- Competition Agreement, (ii) the Confidentiality Agreement, and (iii) as otherwise reasonably outlined and prescribed in writing by the Company’s Chief Executive Officer (collectively, the “ Continuing Obligations ”), your status as an officer and an employee of the Company and any of the Company’s subsidiaries will end effective as of September 30, 2018 (the “ Separation Date ”). On that date, you and the Company shall sign the Separation Agreement and General Release Agreement that is attached hereto as Exhibit A. In the event your employment is terminated as a result of your death prior to the Separation Date, you (or your designated beneficiary) will continue to be entitled to the Separation Benefits set forth in Section 3 of Exhibit A, subject to your (or your beneficiary’s) timely execution thereof. In the event your employment is terminated for a failure to adhere to the Continuing Obligations prior to the Separation Date, you will no longer be eligible for any of the Separation Benefits.	

4.	Choice of Law. This Amendment shall in all respects be governed and construed in accordance with the laws of the State of California, including all matters of construction, validity and performance, without regard to conflicts of law principles.	

5.	Entire Agreement. This Amendment, together with the Offer Letter, Confidentiality Agreement and Non-Compete Agreement contain the entire agreement with respect to the terms of your employment, including the transition and separation of your employment, and supersedes and replaces any prior agreements as to those matters, whether oral or written (including any amounts otherwise payable pursuant to the Executive Severance Agreement) except as expressly set forth herein. For the avoidance of doubt, this Agreement shall not supersede (i) that certain Equity Waiver or (ii) Benefits Waiver, each by and between you and the Company	

dated January 4, 2017. This Amendment shall not be modified or amended except in a writing signed by you and a duly authorized officer of the Company.

IN WITNESS WHEREOF, the undersigned have caused this Amendment to be duly executed and delivered as of the date opposite their respective signatures below.

 

					
DATE: June 9, 2018	 	By: /s/ Derek Newell	 	 	
 	 	Name: Robert Derek Newell

DATE: June 9, 2018	 	CASTLIGHT HEALTH, INC.
	 	 	
 	 	By: /s/ John Doyle	 	 	
 	 	Name: John Doyle
	 	 	
 	 	Title: CEO

                        

                    

                

Exhibit A
Separation Agreement and General Release (see following pages)
SEPARATION AGREEMENT AND GENERAL RELEASE

This Separation Agreement and General Release (“Agreement”) is made as of      __ 2018, by and between Castlight Health, Inc., a Delaware Corporation (“Company”), and Robert Derek Newell (“Employee”). The Agreement is based upon the following recitals of fact, which are hereby incorporated into this Agreement by reference:

A. Employee was employed by Company in the capacity of President.

B. Company and Employee mutually agreed to end Employee’s employment with Company effective as of September 30, 2018 (“Separation Date”).

C. The Company and Employee (collectively, the "Parties") each desire to enter into this Agreement regarding the resignation of Employee from his employment relationship, without admitting any fault or liability, pursuant to the terms and conditions set forth below.

NOW, THEREFORE, IN RELIANCE ON THE ABOVE RECITALS AND IN CONSIDERATION OF THE PROMISES AND COVENANTS SET FORTH BELOW, THE PARTIES MUTUALLY AGREE AS FOLLOWS:

•	Effective Date . This Agreement shall become effective on the eighth (8 th ) day after Employee signs and returns this Agreement to the Company in accordance with Section 15 (“Effective Date”) provided that Employee does not revoke this Agreement prior to such date pursuant to Section 15(f) below and provided further that Employee returns this signed agreement to the Company by no later than [Date] .	

•	Separation of Employment . Employee acknowledges and agrees that (a) Employee’s employment with the Company ceased effective as of the Separation Date; (b) Company has provided Employee a final paycheck that included payment of all remuneration that Employee earned through the Separation Date (subject to Section 3(a) below); (c) Company has provided Employee all forms required under California law; (d) Company has paid all salary, wages, bonuses and any and all other benefits and compensation that Employee earned during his employment with the Company; (e) Employee will submit his final documented expense reimbursement statement within ten (10) days following the Separation Date; and (f) except as otherwise provided in this Agreement, all benefits and perquisites of employment ceased as of the Separation Date and Employee will not receive any further salary, bonuses, vesting of any equity or benefits, or other forms of compensation after the Separation Date from the Company or any of its affiliates.	

•	Separation Benefits . In exchange for Employee’s releases and the promises and covenants contained herein, Employee will be entitled to receive the payments and benefits set forth below:	

◦	Payment of 15 months Base Salary and 15 times the applicable COBRA Coverage, as such terms are defined in that certain Executive Severance Agreement by and between the Company and Employee, dated January	

4, 2017 (the “Executive Severance Agreement”), to be paid at such time and in such manner to be agreed between the Employee and the Company, but not later than January 31, 2019.

◦	Each of Employee’s unvested options to purchase shares of common stock in Jiff, Inc. which were converted into options to purchase shares of the Company’s common stock (all equity grants in Employee's Schwab account that begin with the letter “J”) shall become immediately vested and exercisable as of the Separation Date.	
		
◦	Provided Employee continues to perform his obligations under (i) this Agreement,	
(ii) the Non-Competition Agreement dated January 4, 2017 (the “Non- Competition Agreement”), (iii) the Confidentiality Agreement (defined below), and
(iv) as otherwise reasonably outlined and prescribed in writing by the Company’s Chief Executive Officer as of the Separation Date (collectively, the “Continuing Obligations”), if a definitive agreement governing the terms of a Corporate Transaction (as defined in the Executive Severance Agreement) is executed on or before December 31, 2018, then upon the closing of such Corporate Transaction, Employee shall be entitled to receive (x) 9 months Base Salary and 9 times the applicable COBRA Coverage and (y) the separation benefits to which he would have been entitled in Section 2(b)(ii) of the Executive Severance Agreement upon a Qualifying CIC Termination (as defined in the Executive Severance Agreement). For avoidance of doubt, digital therapeutics are not considered to be the Business of the Company per the Non-competition Agreement dated January 4, 2017, so long as such companies are not currently offering or planning to offer a platform solution at the time Employee provides service to said company.

Employee’s outstanding options to purchase shares of the Company’s common stock (the “Options”) shall cease vesting as of the Separation Date (except as provided in Section 3(b) above and this Section 3(c)), but the Options shall be deemed amended to the extent necessary to provide that the vested portion thereof shall remain exercisable until the earliest of (i) six (6) months from the Separation Date or such longer time so as to permit the exercisability of any options that may vest under Section 3(c) of this Agreement; (ii) the original expiration date of each Option, or (iii) the closing of a Corporate Transaction (as defined in the Executive Severance Agreement). Employee acknowledges and agrees that to the extent the Options constitute “incentive stock options” within the meaning of Section 422 of the Internal Revenue Code of 1986, as amended (the “Code”), the Options shall hereby be deemed modified for the purposes of Section 424 of the Code, shall be treated as nonqualified stock options and, accordingly, at the time of exercise Employee will be required to satisfy all applicable tax withholding requirements that become due upon exercise of the Options.

•	General Release . In consideration of and as a precondition to the Company’s payment of the benefits outlined in this Agreement, which includes consideration to which Employee otherwise would not be entitled, Employee and Company agree as follows:	

◦	Employee, for and on behalf of himself, his agents, heirs, executors, administrators, and assigns, does hereby release and forever discharge the Company, and its successors and assigns, and each of its and their respective directors, officers, employees, shareholders, members, partners, subsidiaries, affiliates (including any sister and parent companies) and each of their respective agents, directors, officers, partners, employees and attorneys (collectively, “Releasees” and individually, “Releasee”), and each of them, from any and all claims, known or unknown, suspected or unsuspected, that Employee has or may have	

relating to, or arising out of the employment of Employee with Company, or any claim for negligence or wrongful termination, including any claim for tortious conduct resulting in personal injuries, any claim for harassment or discrimination on the basis of race, color, national origin, religion, sex, age, sexual orientation, ancestry, medical condition, marital status, physical or mental disability, or other protected class, discharge in violation of public policy and/or violation of any state, federal or local law, regulation, ordinance, constitution, or common law, including without limitation, the Age Discrimination in Employment Act (“ADEA”) and its amendment, the Older Workers Benefits Protection Act, the Americans with Disabilities Act, Title VII of the Civil Rights Act of 1964, as amended, the Fair Labor Standards Acts, as amended, the National Labor Relations Act, as amended, the Labor - Management Relations Act, as amended, the Worker Adjustment and Retraining Notification Act of 1988, as amended, the
Rehabilitation Act of 1973, as amended, the Equal Pay Act, the Pregnancy Discrimination Act, Employee Retirement Income Security Act of 1974, as amended, the Family Medical Leave Act of 1993, as amended, the California Fair Employment and Housing Act, the California Family Rights Act, as amended, the California Business and Professions Code, as amended, and the California Labor Code, and any other applicable laws and/or regulations of any applicable jurisdiction relating to employment or employment discrimination (including without limitation, the Arizona Civil Rights Act, as amended, the Colorado Anti- Discrimination Act, as amended, the Georgia Fair Employment Practices Act, as amended, the Illinois Human Rights Act, as amended, the Massachusetts Fair Employment Practices Act, as amended, the Minnesota Human Rights Act, as amended, the New York Human Rights Law, as amended, the North Carolina Equal Employment Practices Act, as amended, the Pennsylvania Human Relations Act, as amended, the Tennessee Anti-Discrimination Act, as amended, the Texas Commission on Human Rights Act, as amended) and the law of contract and tort. However, this release is not intended to bar any claims that, by statute, may not be waived, such as claims for workers’ compensation benefits, unemployment insurance benefits, or any statutory right to be indemnified for necessary expenditures or losses incurred in the discharge of Employee’s duties under California Labor Code Section 2802.

◦	The Company does hereby release and forever discharge the Employee and his heirs from any and all claims, known or unknown, suspected or unsuspected, that Company has or may have as to the Employee, relating to, or arising out of, the employment of Employee with Company. However, this release is not intended to bar any claims related to the Continuing Obligations, or any claims that, by statute, may not be waived.	

◦	Each of the parties is familiar with section 1542 of the California Civil Code, which reads as follows:	

A general release does not extend to claims which the creditor does not know or suspect to exist in his or her favor at the time of executing the release, which if known by him or her must have materially affected his or her settlement with the debtor.

Each of the parties understands and acknowledge that he or it is releasing unknown claims and waiving all rights he or it has or may have under Civil Code Section 1542 or under any other state statute or common law principle of similar effect based on any acts or failures to act that occurred as of the Effective Date of this Agreement.

		
◦	Nothing herein is intended to release the Company’s statutory obligation under California Labor Code §2802 to indemnify Employee for any losses or expenditures incurred as a direct consequence of discharging his duties.	

•	Covenant Not To Sue . Employee covenants and agrees that he will never, individually or with any person, or through any agent, commence or prosecute against Company or any Releasee any action or other proceeding for any claim which is released or waived in this Agreement (provided, however, that nothing in this Agreement prevents Employee from challenging the waiver of his ADEA claims set forth below in Section 15). The Company covenants and agrees that it will never, individually or with any person, or through any agent, commence or prosecute against Employee any action or other proceeding otherwise covered by Section 4(b). Employee further agrees that he will not aid, assist, abet or in any way encourage any third party or third-party entity to, in any way, pursue any claims of any kind against Company or any Releasee, unless he is specifically required by law to engage in such activity. Company further agrees that it will	
not aid, assist, abet or in any way encourage any third party or third-party entity to, in any way, pursue any claims of any kind against Employee or his heirs, unless it is specifically required by law to engage in such activity. This Agreement shall be deemed breached immediately upon the commencement or prosecution of any such action or proceeding by Employee or Company. Notwithstanding the foregoing, the parties acknowledge and agree that the parties are not waiving or being required to waive any right that cannot be waived as a matter of law, including the right to file a charge with or participate in an investigation by a governmental administrative agency such as the Securities and Exchange Commission, Equal Employment Opportunity Commission or equivalent state or local agency in your state or the National Labor Relations Board. Moreover, nothing in this Agreement is intended to preclude any party from entitlement to any monetary recovery awards by the U.S. Securities Exchange Commission or any other federal, state or local agency in connection with any action asserted by the Securities and Exchange Commission or such federal, state or local agency. Moreover, the Parties acknowledge and agree that the Parties are not waiving or being required to waive any right to sue to enforce this Agreement.

•	Assignment; Authority . Employee represents and warrants that: no other person had or has or claims any interest through Employee in the claims released in this Agreement; he has the sole right and exclusive authority to execute this Agreement; he has the sole right to receive consideration paid therefore; there are no liens or claims of liens or assignments in law or equity or otherwise of or against any of the claims or causes of action or matters released herein; and he has not sold, assigned, transferred, conveyed or otherwise disposed of any claim or demand relating to any matter covered by this Agreement. The rights and obligations of the Parties to this Agreement will be binding on, and will be of benefit to, each of the parties successors, assigns, heirs and estates. For avoidance of doubt, (i) if Employee should die at anytime after this Agreement is signed, all the benefits in Section 3 above shall accrue to his heirs and estates as if Employee were still alive and had fulfilled all his obligations under this Agreement to accrue the benefits in Section 3; and (ii) if there is a Corporate Transaction (as defined in the Executive Severance Agreement), the acquirer will be responsible for all of the obligations under this Agreement.	

•	Confidential Information . Employee acknowledges and agrees that during the course of his employment with the Company, Employee had access to and became acquainted with the Company’s lists of clients, client information, computer programs, contracts, business plans and strategies, prices, reports, financial data and similar confidential or proprietary materials or information about	

the Company’s or its clients’ business and personal affairs. In addition, Employee had access to and became acquainted with confidential information of a personal nature of the Company and its owners, employees, managers and officers, including, but not limited to, such persons’ salaries and benefits, special skills and knowledge, identities and job performance. The parties agree that such business information and information concerning the Company and/or its owners, employees, partners, managers and officers as set forth above and any other information concerning the Company reasonably understood to be confidential constitutes “Confidential Information.” All Confidential Information which came into Employee’s possession shall remain the exclusive property of the Company. Under no circumstances can such Confidential Information be disclosed, disseminated or published in any manner without the prior written consent of the Company. Employee agrees to inform future employers of these obligations and Company may also inform Employee’s future employers of the same as well. This Agreement is in addition to, and does not supersede or affect, any prior confidentiality agreement with the Company to which the Employee may have been subject, including but not limited to Employee’s At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement with the Company (the “Confidentiality Agreement”). Employee hereby represents and warrants that, after the Separation Date, Employee shall comply with all continuing
obligations provided in Employee’s Confidentiality Agreement to the maximum extent permitted by applicable law.

•	Non-Disparagement . Employee agrees that he shall not disparage the Releasees to anyone, including but not limited to, employees and former employees, media or other third parties, or otherwise make statements or take actions (including on social media) which would place the Releasees, or any of them, in a negative light. Similarly, Employee will not disparage any Company product or service to anyone, including but not limited to, employees and former employees, media or other third parties, or otherwise make statements or take actions (including on social media) which would place such service in a negative light. Company agrees that none of its Executive Committee members or members of the Board of Directors shall disparage Employee to anyone, including but not limited to Company employees and former employees, media or other third parties, or otherwise make statements or take action (including on social media) which would place Employee in a negative light.	

•	Company Property . Employee acknowledges and agrees that, to the extent he has not already done so, he shall by the Separation Date deliver to the Company all property of the Company, including, but not limited to, equipment (e.g., laptop computer and cellular telephone), passwords, notebooks, electronic storage devices, credit cards, business cards, keys, parking or building access cards, documents, memoranda, reports, written and computer files and data, books, correspondence, lists, or other written or graphic records, and the like, relating to the Company’s business, that are in Employee’s possession or control, including but not limited to copies (including electronic copies) of any documents or files that contain the Company’s Confidential Information.	

•	Future Cooperation . The Parties agree not to act in any unlawful manner that might damage the business or reputation of the Company, Employee or the Releasees. The Parties agree not to counsel or assist any attorneys or their clients in the presentation or prosecution of any disputes, differences, grievances, claims, charges or complaints by any third party against the Company, Employee and/or any Releasees, unless under subpoena or other court or administrative order or legal process to do so. The Parties further agree both to immediately notify the other Party upon receipt of any court order, subpoena, or other legal discovery device that seeks or might require the disclosure or production of the existence or terms of this Agreement, and to furnish within six (6) business days of their	

receipt, a copy of such subpoena or legal discovery device to the other Party. In addition, the Parties will use reasonable efforts to cooperate with in connection with any existing or potential claims, investigations, administrative proceedings, lawsuits or other legal and business matters which arose during Employee’s employment or that subsequently arise in connection with any business matters in which Employee was involved, as reasonably requested by the Company, provided that such cooperation does not expose Employee to any liability or prejudice his ability to defend himself with respect to any such liability.

•	Waiver, Modification and Amendment . No provision of this Agreement may be waived unless in writing signed by both parties hereto. Waiver of any one provision herein shall not be deemed to be a waiver of any other provision herein. This Agreement may be modified or amended only by a written agreement executed by the parties affected thereby.	

•	Collaborative Effort . The Company has advised Employee to consult with independent legal counsel prior to executing this Agreement. The parties shall bear their own costs and attorneys' fees incurred in negotiating and drafting this Agreement or incurred prior to the date of execution hereof. No party hereto or their respective attorneys shall be deemed to have drafted this Agreement, or any portion thereof, for purposes of	
construing or interpreting any of the terms or provisions in any action or proceeding which may hereinafter arise between them.

•	Execution and Governing Law . This Agreement may be executed in one or more counterparts, each of which shall be deemed an original but all of which together shall constitute a single document. This Agreement is entered into in, and shall be governed by and construed and interpreted in accordance with, the internal laws of the State of California without giving effect to its conflict of laws provisions. Employee acknowledges that he has read this Agreement, understands all of its terms and executes this Agreement voluntarily and with full knowledge of its significance.	

•	Severability . If any term, provision, covenant, or condition of this Agreement (the "Provision") is held by an arbitrator or a court of competent jurisdiction to be invalid, void, or unenforceable, the remaining provisions of this Agreement shall remain in full force and effect and in no way shall be affected, impaired, or invalidated. If possible, the Provision shall remain in effect but shall be modified by the court or arbitrator only to the extent necessary to make it reasonable.	

•	Age Discrimination Disclosure, Review and Revocation . Without detracting in any respect from any other provision of this Agreement:	

◦	In consideration of the separation benefits provided in this Agreement, Employee agrees and acknowledges that this Agreement constitutes a knowing and voluntary waiver of all rights or claims he has or may have against the Company as set forth herein, including, but not limited to, all rights or claims arising under the Age Discrimination in Employment Act of 1967, as amended, including, but not limited to, all claims of age discrimination in employment and all claims of retaliation in violation of the ADEA.	

◦	Employee understands that, by entering into this Agreement, he does not waive rights or claims that may arise after the date of his execution of this Agreement, including without limitation any rights or claims that he may have to secure enforcement of the terms and conditions of this Agreement.	

◦	Employee agrees and acknowledges that the consideration provided to	

his under this Agreement is in addition to anything of value to which he is already entitled.

◦	The Company hereby advises Employee to consult with an attorney prior to executing this Agreement.	

◦	Employee acknowledges that he has at least twenty-one (21) days in which to review and consider this Agreement and, in the event Employee signs and returns this Agreement prior to such twenty-one (21)-day period, Employee acknowledges that he will have done so voluntarily and with full knowledge that he was waiving his right to have twenty-one (21) days to review and consider the Agreement.	

◦	The Company agrees that Employee may revoke this Agreement within seven	
(7) days from the date he signs this Agreement, in which case this Agreement shall be null and void and of no force or effect on either the Company or Employee. Any revocation must be in writing and received by the Company by 5:00 p.m. on or before the seventh (7 th ) day after this Agreement is executed by Employee. Such revocation must be sent to the undersigned.
		
◦	Employee agrees that any change to this Agreement, whether material or immaterial, will not restart the twenty-one (21)-day review period.	

◦	Nothing in this Agreement prevents or precludes Employee from challenging or seeking a determination in good faith of the validity of this waiver under the ADEA, nor does it impose any condition precedent, penalties or costs from doing so, unless specifically authorized by federal law.	

•	Defend Trade Secrets Act . Pursuant to the Defend Trade Secrets Act of 2016 (18	
U.S.C. § 1833b), Employee understands that:

An individual shall not be held criminally or civilly liable under any Federal or State trade secret law for the disclosure of a trade secret that (A) is made (i) in confidence to a Federal, State, or local government official, either directly or indirectly, or to an attorney; and (ii) solely for the purpose of reporting or investigating a suspected violation of law; or (B) is made in a complaint or other document filed in a lawsuit or other proceeding, if such filing is made under seal.

An individual who files a lawsuit for retaliation by an employer for reporting a suspected violation of law may disclose the trade secret to the attorney of the individual and use the trade secret information in the court proceeding, if the individual (A) files any document containing the trade secret under seal; and (B) does not disclose the trade secret, except pursuant to court order.

•	Entire Agreement . Other than expressly excepted herein, this Agreement (along with the Confidentiality Agreement and Non-Competition Agreement) constitutes the entire agreement between and among the parties pertaining to the subject matter hereof and the final, complete and exclusive expression of the terms and conditions of their Agreement. Any and all prior agreements, representations, negotiations and understandings made by the parties, oral and written, express or implied, are hereby superseded and merged herein. This Agreement may be modified, amended or waived, in whole or in part, only by a written agreement executed by the parties affected thereby. If any of the terms or provisions of this Agreement or the Confidentiality Agreement are found to be legally unenforceable, then the remaining terms and conditions shall nevertheless be fully enforceable without regard to the terms or provisions that are found to be legally unenforceable. For the avoidance of doubt, this Agreement shall not supersede (i) that certain	

Equity Waiver, by and between Company and Employee, dated January 4, 2017 or (ii) that certain Benefits Waiver, by and between Company and Employee, dated January 4, 2017 (including, subsections (i)-(iv) thereof). Except as set forth in Employee's Schwab account and in Section 3(b) and 3(c) above, Employee does not have any right to receive or acquire any other security, derivative security or equity of the Company or any Releasee.

•	Not an Admission of Liability . This Agreement, and its performance, does not constitute and will not be construed as an admission by Company or Employee of the truth of any contested matter, or of any liability, wrongful act, or omission.	

•	Breach of Agreement . If, in connection with a breach of this Agreement, either party is required to retain and utilize the services of counsel to enforce this Agreement, the parties agree that the substantially prevailing party in any such enforcement proceeding shall be entitled to its reasonable attorneys’ fees and costs, including costs of expert witnesses, unless otherwise prohibited by law.	

•	Tax and Withholding . All forms of compensation referred to in this Agreement or the Executive Severance Agreement are subject to reduction to reflect applicable withholding and payroll taxes and other deductions required by law. In the event that the payments provided for in this Agreement constitute “parachute payments” within the meaning of	
Code Section 280G, and Employee would be subject to the excise tax imposed by Section 4999 of the Code, then such benefits shall be treated as set forth in Section 4 of the Executive Severance Agreement.

By signing below, each party acknowledges and agrees that he/it has reviewed the terms of this Agreement and knowingly and voluntarily agrees to be bound by them.

	
				
Vicki Ryan	 	 	 	
Chief People Officer

Signature	 	Date	 	
 	 	 	 	
Robert Derek Newell	 	 	 	
 	 	 	 	
Signature	 	Date	

EXHIBIT 31.1
CERTIFICATION OF PRINCIPAL EXECUTIVE OFFICER
PURSUANT TO SECTION 302 OF THE SARBANES-OXLEY ACT OF 2002

I, John C. Doyle, certify that:

1.	I have reviewed this Quarterly Report on Form 10-Q of Castlight Health, Inc.;	

2.	Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;	

3.	Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;	

4.	The registrant’s other certifying officer(s) and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control	
over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

a.	Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;	

b.	Designed such internal control over financial reporting, or caused such internal control over financial	
reporting to be designed under our supervision, to provide reasonable assurance regarding the
reliability of financial reporting and the preparation of financial statements for external purposes in
accordance with generally accepted accounting principles;

c.	Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and	

d.	Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and	

5.	The registrant’s other certifying officer(s) and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions): 	

		
a.	All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and	

b.	Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.	

				
 	C ASTLIGHT  H EALTH , I NC .	
 	By:	 	/s/ John C. Doyle	
Dated:	 	 	John C. Doyle	
August 1, 2018	 	 	Chief Executive Officer (Principal Executive Officer)	

EXHIBIT 31.2
CERTIFICATION OF PRINCIPAL FINANCIAL OFFICER
PURSUANT TO SECTION 302 OF THE SARBANES-OXLEY ACT OF 2002

I, Siobhan Nolan Mangini, certify that:

1.	I have reviewed this Quarterly Report on Form 10-Q of Castlight Health, Inc.;	

2.	Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;	

3.	Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;	

4.	The registrant’s other certifying officer(s) and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control	
over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

a.	Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;	

b.	Designed such internal control over financial reporting, or caused such internal control over financial	
reporting to be designed under our supervision, to provide reasonable assurance regarding the
reliability of financial reporting and the preparation of financial statements for external purposes in
accordance with generally accepted accounting principles;

c.	Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and	

d.	Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and	

5.	The registrant’s other certifying officer(s) and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):	

a.	All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and	

b.	Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.	

				
 	C ASTLIGHT  H EALTH , I NC .	
 	By:	 	/s/ Siobhan Nolan Mangini	
Dated:	 	 	Siobhan Nolan Mangini	
August 1, 2018	 	 	Chief Financial Officer (Principal Financial Officer)	

Exhibit 32.1
CERTIFICATION OF CHIEF EXECUTIVE OFFICER
PURSUANT TO
18 U.S.C. SECTION 1350,
AS ADOPTED PURSUANT TO
SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

Based on my knowledge, I, John C. Doyle, certify, pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that the Quarterly Report of Castlight Health Inc. on Form 10-Q for the quarterly period ended June 30, 2018 fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934 and that information contained in such Form 10-Q fairly presents, in all material respects, the financial condition and results of operations of Castlight Health, Inc.

	
				
 	C ASTLIGHT  H EALTH , I NC .	
 	By:	 	/s/ John C. Doyle	
 	 	 	John C. Doyle	
 	 	 	Chief Executive Officer (Principal Executive Officer)	
Dated:	 	 	 	
August 1, 2018	 	 	 	

Exhibit 32.2
CERTIFICATION OF CHIEF FINANCIAL OFFICER
PURSUANT TO
18 U.S.C. SECTION 1350,
AS ADOPTED PURSUANT TO
SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

Based on my knowledge, I, Siobhan Nolan Mangini, certify, pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that the Quarterly Report of Castlight Health Inc. on Form 10-Q for the quarterly period ended June 30, 2018 fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934 and that information contained in such Form 10-Q fairly presents, in all material respects, the financial condition and results of operations of Castlight Health, Inc.

	
				
 	C ASTLIGHT  H EALTH , I NC .	
 	By:	 	/s/ Siobhan Nolan Mangini	
 	 	 	Siobhan Nolan Mangini	
 	 	 	Chief Financial Officer (Principal Financial Officer)	
Dated:	 	 	 	
August 1, 2018