Document And Entity Information - USD ($) $ in Billions	12 Months Ended
Document And Entity Information - USD ($) $ in Billions	Jan. 31, 2019	Feb. 28, 2019	Jul. 31, 2018
Document And Entity Information [Abstract]
Entity Registrant Name	DOCUSIGN INC
Entity Central Index Key	0001261333
Current Fiscal Year End Date	--01-31
Document Type	10-K
Amendment Flag	false
Entity Emerging Growth Company	true
Entity Ex Transition Period	true
Entity Small Business	false
Entity Shell Company	false
Document Period End Date	Jan. 31, 2019
Document Fiscal Year Focus	2019
Document Fiscal Period Focus	FY
Entity Filer Category	Non-accelerated Filer
Entity Common Stock, Shares Outstanding		169,900,000
Entity Public Float			$ 8.5
Entity Well Known Seasoned Issuer	No
Entity Voluntary Filers	No
Entity Current Reporting Status	Yes

Consolidated Balance Sheets - USD ($) $ in Thousands	Jan. 31, 2019	Jan. 31, 2018
Current assets
Cash and cash equivalents	$ 517,811	$ 256,867
Investments	251,203	0
Restricted cash	367	569
Accounts receivable	174,548	123,750
Contract assets—current	10,616	14,260
Prepaid expenses and other current assets	29,976	23,349
Total current assets	984,521	418,795
Investments—noncurrent	164,220	0
Property and equipment, net	75,832	63,019
Goodwill	195,225	37,306
Intangible assets, net	74,203	14,148
Deferred contract acquisition costs—noncurrent	112,583	75,535
Other assets—noncurrent	8,833	11,170
Total assets	1,615,417	619,973
Current liabilities
Accounts payable	19,590	23,713
Accrued expenses	21,755	15,734
Accrued compensation	77,553	50,852
Contract liabilities—current	381,060	270,188
Deferred rent—current	2,452	1,758
Other liabilities—current	13,903	11,574
Total current liabilities	516,313	373,819
Convertible senior notes, net	438,932	0
Contract liabilities—noncurrent	7,712	7,736
Deferred rent—noncurrent	24,195	23,044
Deferred tax liability—noncurrent	4,207	2,511
Other liabilities—noncurrent	9,696	4,010
Total liabilities	1,001,055	411,120
Commitments and contingencies (Note 11)
Redeemable convertible preferred stock, $0.0001 par value; 0 shares authorized, issued and outstanding as of January 31, 2019; 100,603 shares authorized, 100,226 shares issued and outstanding, $548,910 liquidation preference as of January 31, 2018	0	547,501
Stockholders’ equity (deficit)
Preferred stock, $0.0001 par value; 10,000 shares authorized, 0 shares issued and outstanding as of January 31, 2019; 0 shares authorized, issued and outstanding as of January 31, 2018	0	0
Common stock, $0.0001 par value; 500,000 shares authorized, 169,303 shares outstanding as of January 31, 2019; 185,000 shares authorized, 35,700 shares outstanding as of January 31, 2018	17	4
Additional paid-in capital	1,545,088	160,265
Accumulated other comprehensive (loss) income	(1,965)	3,403
Accumulated deficit	(928,778)	(502,320)
Total stockholders’ equity (deficit)	614,362	(338,648)
Total liabilities, redeemable convertible preferred stock, and stockholders’ equity (deficit)	$ 1,615,417	$ 619,973

Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Thousands	Jan. 31, 2019	Jan. 31, 2018
Statement of Financial Position [Abstract]
Redeemable convertible preferred stock, par value (in usd per share)	$ 0.0001	$ 0.0001
Redeemable convertible preferred stock, shares authorized (in shares)	0	100,603,000
Redeemable convertible preferred stock, shares issued (in shares)	0	100,226,000
Redeemable convertible preferred stock, shares outstanding (in shares)	0	100,226,000
Redeemable convertible preferred stock, liquidation preference		$ 548,910
Preferred stock, par value (in usd per share)	$ 0.0001	$ 0.0001
Preferred stock, shares authorized (in shares)	10,000,000	0
Preferred stock, shares issued (in shares)	0	0
Preferred stock, shares outstanding (in shares)	0	0
Common stock, par value (in usd per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	500,000,000	185,000,000
Common stock, shares outstanding (in shares)	169,303,000	35,700,000

Consolidated Statements of Operations and Comprehensive Loss - USD ($) shares in Thousands, $ in Thousands	12 Months Ended
	Jan. 31, 2019	Jan. 31, 2018	Jan. 31, 2017
Revenue:
Total revenue	$ 700,969	$ 518,504	$ 381,459
Cost of revenue:
Total cost of revenue	192,421	118,273	102,477
Gross profit	508,548	400,231	278,982
Operating expenses:
Sales and marketing	539,606	277,930	240,787
Research and development	185,968	92,428	89,652
General and administrative	209,297	81,526	64,360
Total expenses	934,871	451,884	394,799
Loss from operations	(426,323)	(51,653)	(115,817)
Interest expense	(10,844)	(624)	(611)
Interest income and other income, net	8,959	3,135	1,372
Loss before provision for (benefit from) income taxes	(428,208)	(49,142)	(115,056)
Provision for (benefit from) income taxes	(1,750)	3,134	356
Net loss	$ (426,458)	$ (52,276)	$ (115,412)
Net loss per share attributable to common stockholders, basic and diluted (in usd per share)	$ (3.16)	$ (1.66)	$ (4.17)
Weighted-average number of shares used in computing net loss per share attributable to common stockholders, basic and diluted (in shares)	135,163	32,294	28,020
Other comprehensive income (loss):
Foreign currency translation (losses) gains, net of tax	$ (5,626)	$ 6,149	$ 651
Unrealized gains on investments, net of tax	258	0	0
Other comprehensive (loss) income	(5,368)	6,149	651
Comprehensive loss	(431,826)	(46,127)	(114,761)
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	410,978	29,747	35,443
Sales and marketing
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	172,115	9,386	11,187
Research and development
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	74,108	4,896	10,161
General and administrative
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	122,715	13,578	11,884
Subscription
Revenue:
Total revenue	663,657	484,581	348,563
Cost of revenue:
Total cost of revenue	117,764	83,834	73,363
Subscription \| Cost of revenue
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	16,182	911	1,190
Professional services and other
Revenue:
Total revenue	37,312	33,923	32,896
Cost of revenue:
Total cost of revenue	74,657	34,439	29,114
Professional services and other \| Cost of revenue
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	$ 25,858	$ 976	$ 1,021

Consolidated Statement of Redeemable Convertible Preferred Stock and Stockholders' Equity (Deficit) Statement - USD ($) $ in Thousands	Total	Common Stock	Additional Paid-In Capital	Accumulated Other Comprehensive Loss (Income)	Accumulated Deficit	Redeemable Convertible Preferred Stock
Beginning balance (in shares) at Jan. 31, 2016		27,435,000
Beginning balance at Jan. 31, 2016	$ (276,145)	$ 3	$ 61,881	$ (3,397)	$ (334,632)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)		2,044,000
Exercise of stock options	8,122		8,122
Repurchase of shares from employees (in shares)		(40,000)
Repurchase of shares from employees	(85)		(85)
Employee stock-based compensation expense	34,310		34,310
Non-employee stock-based compensation expense	1,276		1,276
Accretion of preferred stock	(1,456)		(1,456)
Vesting of early exercise liability	1,384		1,384
Net loss	(115,412)				(115,412)
Other comprehensive income, net	651			651
Ending balance (in shares) at Jan. 31, 2017		29,439,000
Ending balance at Jan. 31, 2017	(347,355)	$ 3	105,432	(2,746)	(450,044)
Beginning balance (in shares) at Jan. 31, 2016						100,226,000
Beginning balance at Jan. 31, 2016						$ 544,584
Increase (Decrease) in Temporary Equity [Roll Forward]
Accretion of preferred stock	(1,456)					$ 1,456
Ending balance (in shares) at Jan. 31, 2017						100,226,000
Ending balance at Jan. 31, 2017						$ 546,040
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)		6,261,000
Exercise of stock options	26,433	$ 1	26,432
Employee stock-based compensation expense	28,496		28,496
Non-employee stock-based compensation expense	1,366		1,366
Accretion of preferred stock	(1,461)		(1,461)
Net loss	(52,276)				(52,276)
Other comprehensive income, net	6,149			6,149
Ending balance (in shares) at Jan. 31, 2018		35,700,000
Ending balance at Jan. 31, 2018	(338,648)	$ 4	160,265	3,403	(502,320)
Increase (Decrease) in Temporary Equity [Roll Forward]
Accretion of preferred stock	$ (1,461)					$ 1,461
Ending balance (in shares) at Jan. 31, 2018	100,226,000					100,226,000
Ending balance at Jan. 31, 2018	$ 547,501					$ 547,501
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)	5,791,000	5,791,000
Exercise of stock options	$ 50,211		50,211
Settlement of RSUs (in shares)		8,126,000
Settlement of RSUs	0	$ 1	(1)
Tax withholding on RSU settlement	(215,332)		(215,332)
Employee stock-based compensation expense	411,803		411,803
Non-employee stock-based compensation expense	1,058		1,058
Accretion of preferred stock	(353)		(353)
Issuance of common stock in connection with initial public offering, net of offering costs (in shares)		19,314,000
Issuance of common stock in connection with initial public offering, net of offering costs	524,979	$ 2	524,977
Conversion of redeemable convertible preferred stock to common stock in connection with initial public offering (in shares)		100,350,000
Conversion of redeemable convertible preferred stock to common stock in connection with initial public offering	547,854	$ 10	547,844
Conversion of preferred stock warrant to common stock warrant in connection with initial public offering	848		848
Equity component of Convertible Senior Notes	131,331		131,331
Purchase of capped calls related to issuance of Convertible Senior Notes	(67,563)		(67,563)
Exercise of common stock warrants (in shares)		22,000
Exercise of common stock warrants	0
Net loss	(426,458)				(426,458)
Other comprehensive income, net	(5,368)			(5,368)
Ending balance (in shares) at Jan. 31, 2019		169,303,000
Ending balance at Jan. 31, 2019	614,362	$ 17	$ 1,545,088	$ (1,965)	$ (928,778)
Increase (Decrease) in Temporary Equity [Roll Forward]
Accretion of preferred stock	$ (353)					$ 353
Conversion of redeemable convertible preferred stock to common stock in connection with initial public offering (in shares)						(100,226,000)
Conversion of redeemable convertible preferred stock to common stock in connection with initial public offering						$ (547,854)
Ending balance (in shares) at Jan. 31, 2019	0					0
Ending balance at Jan. 31, 2019	$ 0					$ 0

Consolidated Statements of Cash Flows - USD ($) $ in Thousands	12 Months Ended
	Jan. 31, 2019	Jan. 31, 2018	Jan. 31, 2017
Cash flows from operating activities:
Net loss	$ (426,458)	$ (52,276)	$ (115,412)
Adjustments to reconcile net loss to net cash used in operating activities
Depreciation and amortization	38,027	31,750	28,471
Amortization of deferred contract acquisition and fulfillment costs	42,112	30,377	22,369
Amortization of debt discount and transaction costs	9,507	0	0
Stock-based compensation expense	410,978	29,747	35,443
Deferred income taxes	(5,001)	(996)	12
Other	800	(1,877)	(1,767)
Changes in operating assets and liabilities
Accounts receivable	(42,571)	(28,077)	(17,454)
Contract assets	4,204	(6,934)	(7,111)
Prepaid expenses and other current assets	(3,283)	(1,507)	1,630
Deferred contract acquisition and fulfillment costs	(80,869)	(52,978)	(34,761)
Other assets	2,658	(1,604)	238
Accounts payable	(7,380)	2,864	4,890
Accrued expenses	4,214	5,992	(2,596)
Accrued compensation	26,039	9,168	9,532
Contract liabilities	100,874	87,774	60,440
Deferred rent	1,845	(168)	14,979
Other liabilities	390	3,724	(3,693)
Net cash provided by (used in) operating activities	76,086	54,979	(4,790)
Cash flows from investing activities:
Cash paid for acquisition, net of acquired cash	(218,779)	(299)	0
Purchases of investments	(415,132)	0	0
Proceeds from sale of short-term investments	0	0	1,785
Purchases of property and equipment	(30,413)	(18,929)	(43,330)
Proceeds from sale of business held for sale	0	467	665
Net cash used in investing activities	(664,324)	(18,761)	(40,880)
Cash flows from financing activities:
Proceeds from issuance of convertible senior notes, net of initial purchasers' discounts and transaction costs	560,756	0	0
Purchase of capped calls related to issuance of convertible senior notes	(67,563)	0	0
Proceeds from issuance of common stock in initial public offering, net of underwriting commissions	529,305	0	0
Payment of tax withholding obligation on RSU settlement	(215,332)	0	0
Proceeds from the exercise of stock options	50,211	26,433	8,122
Payment of deferred offering costs	(4,011)	(315)	0
Other financing	(250)	(390)	(85)
Net cash provided by financing activities	853,116	25,728	8,037
Effect of foreign exchange on cash, cash equivalents and restricted cash	(4,136)	4,246	(334)
Net increase in cash, cash equivalents and restricted cash	260,742	66,192	(37,967)
Cash, cash equivalents and restricted cash at beginning of period	257,436	191,244	229,211
Cash, cash equivalents and restricted cash at end of period	518,178	257,436	191,244
Supplemental disclosure:
Cash paid for interest	204	599	602
Cash paid for taxes	3,213	617	229
Non-cash investing and financing activities:
Property and equipment in accounts payable and other accrued liabilities	2,293	3,967	3,325
Conversion of redeemable convertible preferred stock to common stock in connection with initial public offering	547,854	0	0
Conversion of preferred stock warrant to common stock warrant in connection with initial public offering	848	0	0
Preferred stock accretion	353	1,461	1,456
Vesting of early exercised stock options	0	0	1,384
Deferred offering costs accrued and unpaid	0	1,381	0
Estimated fair value of office under build-to-suit lease	$ 2,479	$ 0	$ 0

Summary of Significant Accounting Policies

12 Months Ended

Jan. 31, 2019

Accounting Policies [Abstract]

Summary of Significant Accounting Policies

Organization and Description of Business

DocuSign, Inc. (“we,” “our” or “us”) was incorporated in the State of Washington in April 2003. We merged with and into DocuSign, Inc., a Delaware corporation, in March 2015.

We provide a platform that enables businesses of all sizes to digitally prepare, execute and act on agreements, thereby simplifying and accelerating the process of doing business.

Basis of Presentation and Principles of Consolidation

Our consolidated financial statements include those of DocuSign, Inc. and our subsidiaries, after elimination of all intercompany accounts and transactions. We have prepared the accompanying consolidated financial statements in accordance with accounting principles generally accepted in the United States of America (“U.S. GAAP”). Our fiscal year ends on January 31. References to fiscal 2019, for example, are to the fiscal year ended January 31, 2019.

Certain prior year amounts have been reclassified to conform to current year presentation. These amounts were not material to any of the periods presented.

Initial Public Offering

On May 1, 2018, we completed our initial public offering, or IPO, in which we issued and sold 19.3 million shares of common stock at price to the public of $29.00 per share, including 3.3 million shares of common stock purchased by the underwriters in the full exercise of the over-allotment option granted to them. Certain of our existing stockholders sold an additional 5.6 million shares at the public offering price. We received net proceeds of $523.9 million after deducting underwriting discounts and commissions of $30.8 million and offering expenses of $5.4 million. We did not receive any proceeds from the sale of shares by our stockholders.

Upon the completion of our IPO, all 100.2 million shares of our convertible preferred stock automatically converted into an aggregate of 100.4 million shares of our common stock; all our outstanding warrants to purchase shares of convertible preferred stock converted into warrants to purchase 22,468 shares of common stock with the related warrant liability of $0.8 million reclassified into additional paid-in capital; and our Amended and Restated Certificate of Incorporation was filed and went in effect authorizing a total of 500.0 million shares of common stock and 10.0 million shares of preferred stock.

Follow-On Offering

On September 18, 2018, we completed our follow-on offering, in which certain stockholders sold 8.1 million shares of common stock. The price per share to the public was $55.00. We did not receive any proceeds from the sale of shares by the selling stockholders. We incurred and expensed issuance costs of $1.3 million associated with the sale of such shares.

Use of Estimates

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates.

Significant items subject to such estimates and assumptions include those related to the allocation of revenue between recognized and deferred amounts, allowance for bad debts, goodwill, intangible assets, deferred contract acquisition costs, customer benefit period, fair value of financial instruments, valuation of stock-based compensation, valuation of common stock, fair value of the liability and equity components of the convertible notes, valuation of the build-to-suit lease, and the valuation allowance for deferred income taxes.

Concentration of Credit Risk

Our financial instruments that are exposed to concentrations of credit risk consist primarily of cash, cash equivalents, marketable securities and accounts receivable. Although we deposit our cash with multiple financial institutions, the deposits, at times, may exceed federally insured limits. We have not experienced any losses on our deposits of cash and cash equivalents. Cash equivalents consist of money market funds which are invested through financial institutions in the U.S. Management believes that the institutions are financially stable and, accordingly, minimal credit risk exists.

No customer individually accounted for more than 10% of our revenues in the years ended January 31, 2019, 2018 and 2017. One of our customers accounted for 10% of our accounts receivable as of January 31, 2019 and 2018. We perform ongoing credit evaluations of our customers, do not require collateral and maintain allowances for potential credit losses on customers’ accounts when deemed necessary.

Revenue Recognition

We recognize revenue when a customer obtains control of promised services. The amount of revenue recognized reflects the consideration that we expect to be entitled to receive in exchange for these services. To achieve the core principle of this new standard, we apply the following steps:

1. Identification of the contract, or contracts, with the customer

We consider the terms and conditions of the contract and our customary business practices in identifying our contracts under ASC 606. We determine we have a contract with a customer when the contract is approved, we can identify each party’s rights regarding the services to be transferred, we can identify the payment terms for the services, we have determined the customer has the ability and intent to pay and the contract has commercial substance. At contract inception we evaluate whether two or more contracts should be combined and accounted for as a single contract and whether the combined or single contract includes more than one performance obligation. We apply judgment in determining the customer’s ability and intent to pay, which is based on a variety of factors, including the customer’s historical payment experience or, in the case of a new customer, credit and financial information pertaining to the customer.

2. Identification of the performance obligations in the contract

Performance obligations promised in a contract are identified based on the services and the products that will be transferred to the customer that are both capable of being distinct, whereby the customer can benefit from the service either on its own or together with other resources that are readily available from third parties or from us, and are distinct in the context of the contract, whereby the transfer of the services and the products is separately identifiable from other promises in the contract. Our performance obligations consist of (i) subscription services, (ii) professional services, (iii) on-premises solutions, and (iv) maintenance and support for on-premises solutions.

3. Determination of the transaction price

The transaction price is determined based on the consideration to which we expect to be entitled in exchange for transferring services to the customer. Variable consideration is included in the transaction price if, in our judgment, it is probable that a significant future reversal of cumulative revenue under the contract will not occur. None of our contracts contain a significant financing component.

4. Allocation of the transaction price to the performance obligation in the contract

If the contract contains a single performance obligation, the entire transaction price is allocated to the single performance obligation. Contracts that contain multiple performance obligations require an allocation of the transaction price to each performance obligation based on a relative standalone selling price (“SSP”).

5. Recognition of the revenue when, or as, we satisfy a performance obligation

Revenue is recognized at the time the related performance obligation is satisfied by transferring the control of the promised service to a customer. Revenue is recognized as control of the service is transferred to the customer, in an amount that reflects the consideration that we expect to receive in exchange for those services. We generate all our revenue from contracts with customers.

Subscription Revenue

We generate revenue primarily from sales of subscriptions to access our software suite and related subscriptions of our customers. Our subscription revenue is driven by our go-to-market model, which includes a combination of direct sales, partner-assisted sales and web-based self-service purchasing. Subscription arrangements with customers do not provide the customer with the right to take possession of our software operating our software suite at any time. Instead, customers are granted continuous access to our software suite over the contractual period. A time-elapsed method is used to measure progress because we transfer control evenly over the contractual period. Accordingly, the fixed consideration related to subscription revenue is generally recognized on a straight-line basis over the contract term beginning on the date access to our software suite is provided, as long as other revenue recognition criteria have been met.

The typical subscription term is one to three years. Most of our contracts are non-cancelable over the contractual term. Customers typically have the right to terminate their contracts for cause if we fail to perform in accordance with the contractual terms. Some of our customers have the option to purchase additional subscription services at a stated price. These options are evaluated on a case-by-case basis but generally do not provide a material right as they are priced at or above our SSP and, as such, would not result in a separate performance obligation.

Professional Services and Other Revenue

Professional services and other revenue consists of fees associated with consulting and training services from assisting customers in implementing and expanding the use of our software suite. These services are distinct from subscription services. Professional services do not result in significant customization of the subscription service. Revenue from professional services provided on a time and materials basis is recognized as the services are performed. Other revenue includes amounts derived from the sale of our on-premises solutions, which are recognized upon passage of control, which occurs upon shipment of the product. The maintenance and support on the on-premises solutions is a stand-ready obligation to perform this service over the term of the arrangement and, as a result, is accounted for ratably over the term of the arrangement.

Contracts with Multiple Performance Obligations

Most of our contracts with customers contain multiple performance obligations that are distinct and accounted for separately. The transaction price is allocated to the separate performance obligations on a relative SSP basis. We determine SSP for all our performance obligations using observable inputs, such as standalone sales and historical contract pricing. SSP is consistent with our overall pricing objectives, taking into consideration the type of subscription services and professional and other services. SSP also reflects the amount we would charge for that performance obligation if it were sold separately in a standalone sale, and the price we would sell to similar customers in similar circumstances.

Variable Consideration

Revenue from sales is recorded at the net sales price, which is the transaction price, and includes estimates of variable consideration. The amount of variable consideration that is included in the transaction price is constrained and is included in the net sales price only to the extent that it is probable that a significant reversal in the amount of the cumulative revenue will not occur when the uncertainty is resolved.

If our services do not meet certain service level commitments, our customers are entitled to receive service credits, and in certain cases, refunds, each representing a form of variable consideration. We have historically not experienced any significant incidents affecting the defined levels of reliability and performance as required by our subscription contracts. Accordingly, the amount of any estimated refunds related to these agreements in the consolidated financial statements is not material during the periods presented.

Deferred Contract Acquisition Costs

We capitalize sales commissions, certain parts of the company bonus and associated payroll taxes paid to internal sales personnel that are incremental to the acquisition of customer contracts. These costs are recorded as deferred contract acquisition costs on the consolidated balance sheets. We determine whether costs should be deferred based on our sales compensation plans, if the commissions are in fact incremental and would not have occurred absent the customer contract.

Sales commissions for renewal of a subscription contract are not considered commensurate with the commissions paid for the acquisition of the initial subscription contract given the substantive difference in commission rates between new and renewal

contracts. Commissions paid upon the initial acquisition of a contract are amortized over an estimated period of benefit of five years while commissions paid related to renewal contracts are amortized over an estimated period of benefit of two years. Amortization is recognized on a straight-line basis commensurate with the pattern of revenue recognition.

Commissions paid on professional services are typically amortized in accordance with the associated revenue as the commissions paid on new and renewal professional services are commensurate with each other. We determine the period of benefit for commissions paid for the acquisition of the initial subscription contract by taking into consideration our initial estimated customer life and the technological life of our software suite and related significant features. We determine the period of benefit for renewal subscription contracts by considering the average contractual term for renewal contracts. Amortization of deferred contract acquisition costs is primarily included in the “Sales and marketing” expense in the consolidated statements of operations and comprehensive loss.

We periodically review these deferred costs to determine whether events or changes in circumstances have occurred that could impact the period of benefit of these deferred contract acquisition costs. There were no material impairment losses recorded during the periods presented.

Deferred Contract Fulfillment Costs

We capitalize third-party costs to fulfill contracts with a customer in “Prepaid expenses and other current assets” and “Other assets—noncurrent” on our consolidated balance sheets. We amortize these costs consistent with the ratable revenue recognition of the performance obligations in the associated contracts. We assess these costs for impairment at the end of each reporting period.

Cost of Revenue

“Subscription” cost of revenue primarily consists of personnel and related costs to support our software suite, amortization expense associated with capitalized internally developed software and intangible assets, property and equipment depreciation, allocated overhead expenses, merchant processing fees and server hosting costs.

“Professional services and other” cost of revenue consists primarily of personnel costs for our professional services delivery team, travel-related costs and allocated overhead.

Advertising

Advertising costs are expensed as incurred and are included in “Sales and marketing” expense in our consolidated statements of operations and comprehensive loss. Advertising expense was $34.1 million, $19.3 million and $23.6 million in the years ended January 31, 2019, 2018 and 2017.

Research and Development

Research and development costs are expensed as incurred and consist primarily of personnel costs, including salaries, bonuses and benefits, and stock-based compensation. They also include amortization associated with acquired intangible assets and allocated overhead.

Stock-Based Compensation

Compensation cost for stock-based awards issued to employees, including stock options and restricted stock units, or RSUs, is measured at fair value on the date of grant and recognized over the service period. The fair value of stock options is estimated on the date of grant using a Black-Scholes model. The fair value of RSUs is estimated on the date of grant based on the fair value of our underlying common stock.

We recognize compensation expense for stock options on a straight-line basis over the requisite service period. Compensation expense for RSUs granted prior to January 31, 2018, is amortized on a graded basis over the requisite service period as long as the performance condition in the form of a specified liquidity event is probable to occur. The liquidity event condition was satisfied upon the effectiveness of our registration statement on Form S-1, or IPO Registration Statement, on April 26, 2018. On that date we recorded a cumulative stock-based compensation expense of $262.8 million using the accelerated attribution method for all the RSUs, for which the service condition has been fully satisfied as of April 26, 2018. The remaining unrecognized stock-based compensation expense related to the RSUs will be recorded over their remaining requisite service periods. RSUs granted after January 31, 2018, generally vest on the satisfaction of service-based condition only. We recognize compensation expense for such RSUs on a straight-line basis over the requisite service period.

From time-to-time, we grant RSUs that also include performance-based or market-based conditions. For RSUs granted with a performance condition, we recognize expense on a graded vesting basis over the vesting period, after assessing the probability of achieving requisite performance criteria. For RSUs granted with a market condition, we use a lattice model simulation analysis which captures the impact of the vesting conditions to value the performance stock units and recognize the expense on a graded basis.

We recognize compensation expense related to shares issued pursuant to the employee stock purchase plan (ESPP) on a straight-line basis over the offering period.

Compensation expense is recognized net of forfeitures that are estimated at the time of grant and revised in subsequent periods if actual forfeitures differ from those estimates. In the years ended January 31, 2019, 2018 and 2017, total stock-based compensation expense was $411.0 million, $29.7 million and $35.4 million. Recognized tax benefits on total stock-based compensation expense, which are reflected in the "provision for income taxes" in the consolidated statements of operations and comprehensive loss, were $1.7 million in the year ended January 31, 2019 and immaterial in the years ended January 31, 2018 and 2017.

We account for equity instruments issued to non-employees at fair value of the consideration received or fair value of the equity instrument issued, whichever is more reliably measurable. The measurement date of the fair value of the equity instrument issued is the earlier of the date on which the counterparty’s performance is complete or the date on which it is probable that performance will occur. Compensation expense related to stock-based awards issued to non-employees was $1.1 million, $1.4 million and $1.3 million in the years ended January 31, 2019, 2018 and 2017.

We capitalize stock-based compensation costs incurred as a result of qualifying internally-developed software development activities. Capitalized stock-based compensation was $1.9 million in the year ended January 31, 2019 and $0.1 million in each of the years ended January 31, 2018 and 2017.

We may elect to issue shares on the settlement dates net of the minimum statutory tax withholding requirements to be paid by us on behalf of our employees. In these instances, we record the liability for withholding amounts to be paid by us as a reduction to additional paid-in capital when paid, and include these payments as a reduction of cash flows from financing activities.

Income Taxes

We are subject to income taxes in the U.S. and numerous foreign jurisdictions. These foreign jurisdictions have different statutory tax rates than the U.S. We record a provision for income taxes for the anticipated tax consequences of the reported results of operations using the asset and liability method. Under this method, we recognize deferred tax assets and liabilities for the expected future tax consequences of temporary differences between the financial reporting and tax basis of assets and liabilities, as well as for operating loss and tax credit carryforwards. Deferred tax assets and liabilities are measured using the tax rates that are expected to apply to taxable income for the years in which those tax assets and liabilities are expected to be realized or settled. We record a valuation allowance to reduce our deferred tax assets to the net amount that we believe is more likely than not to be realized.

We recognize tax benefits from uncertain tax positions only if we believe that it is more likely than not that the tax position will be sustained on examination by the taxing authorities based on the technical merits of the position. As we expand internationally, we will face increased complexity in determining the appropriate tax jurisdictions for revenue and expense items. As a result, we may record unrecognized tax benefits in the future. Our policy is to adjust these reserves when facts and circumstances change, such as the closing of a tax audit or the refinement of an estimate. To the extent that the final tax outcome of these matters is different than the amounts recorded, such differences will affect the provision for income taxes in the period in which such determination is made and could have a material impact on our financial condition and operating results. The provision for income taxes includes the effects of any accruals that we believe are appropriate, as well as the related net interest and penalties.

We intend to indefinitely reinvest any undistributed and future earnings from our foreign operations outside of the U.S. As of January 31, 2019, and 2018, no provision for applicable income taxes has been provided thereon. Upon distribution of those earnings, we would be subject to withholding taxes payable to various foreign countries. As of January 31, 2019, any foreign withholding taxes potentially payable on the undistributed earnings of our foreign subsidiaries were immaterial.

Foreign Currency

The functional currency of our foreign entities is generally the local currency. The functional currency of our branches is the U.S. dollar. For branches where the U.S. dollar is the functional currency, foreign currency denominated monetary assets and liabilities are re-measured into U.S. dollars at current exchange rates and foreign currency denominated nonmonetary assets and liabilities are re-measured into U.S. dollars at historical exchange rates. We recognize gains and losses from transaction adjustments within "Interest income and other income, net" in the consolidated statements of operations and comprehensive loss in the period of occurrence. We recorded a foreign currency transaction loss of $3.4 million in the year ended January 31, 2019 and a foreign currency transaction gain of $2.2 million and $2.0 million in the years ended January 31, 2018 and 2017.

We present our financial statements in U.S. dollars. Adjustments resulting from translating foreign functional currency financial statements into U.S. dollars are recorded as a separate component on our consolidated statements of comprehensive loss, net of tax. All assets and liabilities denominated in a foreign currency are translated at the exchange rate on the balance sheet date. Revenues and expenses are translated at the average exchange rate during the period. Equity transactions are translated using the historical exchange rate.

Net Loss Per Share Attributable to Common Stockholders

In periods when we have net income, we compute basic and diluted net loss per share in conformity with the two-class method required for participating securities. The undistributed earnings are allocated between common stock and participating securities as if all earnings had been distributed during the period presented. We consider all series of convertible preferred stock to be participating securities as the holders of such stock are entitled to receive noncumulative dividends on a pari passu basis in the event that a dividend is paid on common stock. We also consider any shares issued on the early exercise of stock options subject to repurchase to be participating securities because holders of such shares have non-forfeitable dividend rights in the event a dividend is paid on common stock. The holders of convertible preferred stock and early exercised shares do not have a contractual obligation to share in our losses. As such, our net losses in the years ended January 31, 2019, 2018 and 2017 were not allocated to these participating securities.

Basic net loss per share attributable to common stockholders is computed by dividing the net loss attributable to common stockholders by the weighted-average number of shares of common stock outstanding during the period. Diluted net loss per share attributable to common stockholders is computed by giving effect to all potential shares of common stock, including common stock underlying our convertible preferred stock, our warrants to purchase common stock, and convertible preferred stock, early exercised stock options and outstanding stock options, to the extent they are dilutive.

Since we have reported net losses for all periods presented, diluted net loss per share attributable to common stockholders is the same as basic net loss per share attributable to common stockholders. Dilutive common shares are not assumed to have been issued as their effect would have been antidilutive.

Cash and Cash Equivalents

We consider all highly liquid investments purchased with maturities of three months or less at the date of purchase to be cash equivalents.

Investments

Investments consist of money market funds, commercial paper, corporate notes and bonds, as well as U.S. treasury and government agency securities. Management determines the appropriate classification of investments at the time of purchase and reevaluates such determination at each balance sheet date. Investments with original maturities of more than three months are classified as available-for-sale and are carried at fair value in the consolidated balance sheet, with all unrealized gains and losses reflected in “Other comprehensive income (loss)” on the consolidated balance sheets. These securities are classified as short-term or long-term based on their remaining contractual maturities.

We evaluate our investments to assess whether those with unrealized loss positions are other than temporarily impaired. We consider impairments to be other than temporary if they are related to deterioration in credit risk or if it is likely we will sell the securities before the recovery of their cost basis. Realized gains and losses and declines in value judged to be other than temporary are determined based on the specific identification method and are reported in "interest income and other income, net" in the consolidated statements of operations and comprehensive loss.

Restricted Cash

Restricted cash primarily consists of a money market account and certificates of deposits collateralizing our operating lease agreements for office space.

Fair Value of Financial Instruments

We measure assets and liabilities at fair value based on an expected exit price, which represents the amount that would be received on the sale of an asset or paid to transfer a liability in an orderly transaction between market participants. As such, fair value may be based on assumptions that market participants would use in pricing an asset or liability. The authoritative guidance on fair value measurements establishes a consistent framework for measuring fair value on either a recurring or nonrecurring basis whereby inputs, used in valuation techniques, are assigned a hierarchical level. The following are the hierarchical levels of inputs to measure fair value:



Level 1		Observable inputs that reflect quoted prices (unadjusted) for identical assets or liabilities in active markets.

Level 2		Inputs reflect quoted prices for identical assets or liabilities in markets that are not active; quoted prices for similar assets or liabilities in active markets; inputs other than quoted prices that are observable for the assets or liabilities; or inputs that are derived principally from or corroborated by observable market data by correlation or other means.

Level 3		Unobservable inputs reflecting our own assumptions incorporated in valuation techniques used to determine fair value. These assumptions are required to be consistent with market participant assumptions that are reasonably available

Assets and liabilities are classified in their entirety based on the lowest level of input that is significant to the fair value measurement. Our assessment of the significance of a particular input to the fair value measurement requires judgment and may affect the placement of assets and liabilities being measured within the fair value hierarchy.

The carrying values of our financial instruments, including cash and cash equivalents, accounts receivable and accounts payable approximate their respective fair values due to the short period of time to maturity, receipt or payment.

Accounts Receivable, Unbilled Accounts Receivable and Allowance for Doubtful Accounts

Accounts receivable primarily consist of amounts billed currently due from customers. Our accounts receivable are subject to collection risk. Gross accounts receivable are reduced for this risk by an allowance for doubtful accounts. This allowance is for estimated losses resulting from the inability of our customers to make required payments. It is an estimate and is regularly evaluated for adequacy by taking into consideration a combination of factors. To determine whether a provision for doubtful accounts should be recorded, we look at such factors as past collection experience, credit quality of the customer, age of the receivable balance, and current economic conditions. The allowance for doubtful accounts was $0.6 million and $0.3 million as of January 31, 2019 and 2018. We do not have any off-balance-sheet credit exposure related to our customers.

Unbilled accounts receivable represent amounts for which we have recognized revenue, pursuant to our revenue recognition policy, for professional services already performed, but billed in arrears. The unbilled accounts receivable balance was $1.5 million and $0.8 million as of January 31, 2019 and 2018.

We do not typically offer right of refund in our contracts. The allowance for doubtful accounts reflects our best estimate of probable losses inherent in our receivables portfolio determined on the basis of historical experience, specific allowances for known troubled accounts and other currently available evidence. We have not experienced significant credit losses from our accounts receivable. We perform a regular review of our customers’ payment histories and associated credit risks and do not require collateral from our customers. Changes in the allowance for doubtful accounts were not material in the years ended January 31, 2019, 2018 and 2017.

Property and Equipment

Property and equipment, including costs incurred to bring to the location and condition necessary for intended use, are recorded at cost and depreciated over their estimated useful lives using the straight-line method and the following estimated useful lives:



	Estimated Useful Life
Computer and network equipment	2-3 years
Software, including capitalized software development costs	3 years
Furniture and office equipment	3-4 years
Leasehold improvements	Lesser of lease term and 10 years

Disposals are removed at cost less accumulated depreciation, and any gain or loss from disposition is reflected in the statement of operations in the year of disposition. Additions and improvements that increase the value or extend the life of an asset are capitalized. Maintenance and repairs are expensed as incurred.

We are deemed to be the owner, for accounting purposes, during the construction phase of certain long-lived assets under a build-to-suit lease arrangement because of our involvement with the construction, our exposure to any potential cost overruns or our other commitments under the arrangements. In these cases, we recognize build-to-suit lease assets under construction and corresponding build-to-suit lease liabilities on our consolidated balance sheets. Once construction is completed, if a lease meets certain “sale-leaseback” criteria, we remove the asset and liability and account for the lease as an operating lease. Otherwise, the lease is accounted for as a capital lease.

Goodwill

Goodwill represents the excess of the purchase price over the fair value of net assets acquired in business combinations accounted for using the acquisition method of accounting and is not amortized. We test goodwill for impairment at least annually, in the fourth quarter of each year, or as events occur or circumstances change that would more likely than not reduce the fair value of a reporting unit below its carrying amount. Our test for goodwill impairment starts with a qualitative assessment to determine whether it is necessary to perform the quantitative goodwill impairment test. If qualitative factors indicate that the fair value of the reporting unit is more likely than not less than its carrying amount, then a quantitative goodwill impairment test is performed. For the purposes of impairment testing, we have determined that we have one operating segment and one reporting unit. There was no impairment of goodwill recorded in the years ended January 31, 2019, 2018 and 2017.

Intangible Assets

Intangible assets with finite lives are amortized using the straight-line method over their estimated useful lives. The estimated useful lives of intangible assets, estimated based on our expected period of benefit, are as follows:



	Estimated Useful Life
Customer contracts & related relationships	5-9 years
Certifications	5 years
Maintenance contracts & related relationships	5 years
Existing technology	3 years
Backlog—subscription	2 years
Tradenames/trademarks	1-2 years

Impairment of Long-Lived Assets

We review long-lived assets, including property and equipment and intangible assets, for impairment whenever events or changes in business circumstances indicate that the carrying amount of the assets may not be fully recoverable. Such events and changes may include: significant changes in performance relative to expected operating results, significant changes in asset use, significant negative industry or economic trends, and changes in our business strategy. An impairment loss is recognized when estimated undiscounted future cash flows expected to result from the use of the asset and its eventual disposition are less than its carrying amount. No assets were determined to be impaired as of January 31, 2019 or 2018.

Software Development Costs

We capitalize qualifying internally-developed software development costs incurred during the application development stage, as long as it is probable the project will be completed, and the software will be used to perform the function intended. Capitalization of such costs ceases once the project is substantially complete and ready for its intended use. Capitalized software development costs are included in “Property and equipment, net” on our consolidated balance sheets and are amortized on a straight-line basis over their expected useful lives of approximately three years. We capitalized $7.6 million, $2.4 million and $3.3 million of internally developed software in the years ended January 31, 2019, 2018 and 2017. We recorded amortization expense related to capitalized software development costs of $2.8 million, $3.6 million and $4.6 million in the respective years.

Business Combinations

We account for our acquisitions using the acquisition method of accounting, which requires, among other things, allocation of the fair value of purchase consideration to the tangible and intangible assets acquired and liabilities assumed at their estimated fair values on the acquisition date. The excess of the fair value of purchase consideration over the values of these identifiable assets and liabilities is recorded as goodwill. When determining the fair value of assets acquired and liabilities assumed, management makes significant estimates and assumptions, especially with respect to intangible assets. Management’s estimates of fair value are based upon assumptions believed to be reasonable, but which are inherently uncertain and unpredictable and, as a result, actual results may differ from estimates. During the measurement period, not to exceed one year from the date of acquisition, we may record adjustments to the assets acquired and liabilities assumed, with a corresponding offset to goodwill if new information is obtained related to facts and circumstances that existed as of the acquisition date. After the measurement period, any subsequent adjustments are reflected in the consolidated statements of operations and comprehensive loss.

Acquisition costs, such as legal and consulting fees, are expensed as incurred.

Segments

Operating segments are defined as components of an entity for which separate financial information is available and that is regularly reviewed by the Chief Operating Decision Maker, or the CODM, in deciding how to allocate resources to an individual segment and in assessing performance. Our Chief Executive Officer is our CODM. Our CODM reviews financial information presented on a consolidated basis for purposes of making operating decisions, allocating resources, and evaluating financial performance. As such, we have determined that we operate in one operating and one reportable segment.

Legal Contingencies

We expect to periodically evaluate developments in our legal matters that could affect the amount of liability that we accrue, if any, and adjust, as appropriate. Until the final resolution of any such matter for which we may be required to record a liability, there may be a loss exposure in excess of the liability recorded and such amount could be significant. We expense legal fees as incurred.

Recent Accounting Pronouncements

In February 2016, the Financial Accounting Standards Board, or the FASB, issued accounting standards update ("ASU") No. 2016-02, Leases (Topic 842), which supersedes current guidance related to accounting for leases. This guidance is intended to increase transparency and comparability among organizations by recognizing lease assets and lease liabilities on the balance sheet and disclosing key information about leasing arrangements. In July 2018, the FASB issued ASU No. 2018-10, Codification Improvements to Topic 842, Leases. The ASU makes 16 technical corrections to the new leases standard and other accounting topics, alleviating unintended consequences from applying the new standard. It does not make any substantive changes to the core provisions or principles of the new standard. In July 2018, the FASB also issued ASU No. 2018-11, Leases (Topic 842). The ASU provides (1) an optional transition method that entities can use when adopting the standard and (2) a practical expedient that permits lessors to not separate nonlease components from the associated lease component if certain conditions are met.

The standard is effective for public entities for annual and interim reporting periods beginning after December 15, 2018. Early adoption is permitted. We will adopt the new standard as of February 1, 2019 and will recognize a cumulative-effect adjustment to the opening balance of accumulated deficit as of the adoption date. We will elect the optional transition approach to not apply Topic 842 in the comparative periods presented and the package of practical expedients. We will adopt all available practical expedients, as applicable. We expect that the adoption of Topic 842 will result in the recognition of total right-of-use assets between $80.0 million and $100.0 million and total lease liabilities between $110.0 million and $130.0 million, with the most significant impact related to our office space leases. We do not expect the adoption of Topic 842 to have a material impact to the consolidated statements of operations or to have any impact on its cash flows from operating, investing or financing activities.

In June 2016, the FASB issued ASU No. 2016-13, Financial Instruments—Credit Losses (Topic 326). ASU 2016-13 changes the impairment model for most financial assets, and will require the use of an expected loss model in place of the currently used incurred loss method. Under this model, entities will be required to estimate the lifetime expected credit loss on such instruments and record an allowance to offset the amortized cost basis of the financial asset, resulting in a net presentation of the amount expected to be collected on the financial asset. The update to the standard is effective for interim and annual periods beginning after December 15, 2019. We are evaluating the impact of the adoption of ASU 2016-13 on our consolidated financial statements.

In February 2018, the FASB issued ASU No. 2018-02, Income Statement—Reporting Comprehensive Income (Topic 220), which allows a reclassification from accumulated other comprehensive income to retained earnings for stranded tax effects resulting from the Tax Cuts and Jobs Act, the Tax Act. As the amendment only relates to the reclassification of the income tax effects of the U.S. Tax Act, the underlying guidance that requires that the effect of a change in tax laws or rates be included in income from continuing operations is not affected. The standard is effective for annual and interim reporting periods beginning after December 15, 2018 for all entities. The amendment is to be applied either in the period of adoption or retrospectively to each period in which the effect of the change in the U.S. federal corporate income tax rate in the Tax Act is recognized. Early adoption is permitted. The adoption of the standard is not expected to have a material impact on our consolidated financial statements.

In June 2018, the FASB issued ASU No. 2018-07, Compensation—Stock Compensation (Topic 718): Improvements to Nonemployee Share-Based Payment Accounting. The ASU aligns the measurement and classification guidance for stock-based payments to nonemployees with the guidance for stock-based payments to employees, with certain exceptions. Under the guidance, the measurement of equity-classified nonemployee awards will be fixed at the grant date. The ASU is effective for public business entities in annual periods beginning after December 15, 2018, and interim periods within those years. Early adoption is permitted, including in an interim period, but not before an entity adopts the Topic 606 revenue guidance. The adoption of the standard is not expected to have a material impact on our consolidated financial statements.

In July 2018, the FASB issued ASU No. 2018-09, Codification Improvements, which clarifies, corrects errors in and makes improvements to several topics in the FASB Accounting Standard Codification. The transition and effective date guidance is based on the facts and circumstances of each amendment. Some of the amendments do not require transition guidance and were effective upon issuance of the ASU. Amendments that do have transition guidance are effective for public business entities for annual periods beginning after December 15, 2018. The adoption of the standard is not expected to have a material impact on our consolidated financial statements.

In August 2018, the FASB issued ASU No. 2018-13, Fair Value Measurement (Topic 820), which modifies, removes and adds certain disclosure requirements on fair value measurements based on the FASB Concepts Statement, Conceptual Framework for Financial Reporting—Chapter 8: Notes to Financial Statements. The ASU is effective for all entities for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2019. The amendments on changes in unrealized gains and losses, the range and weighted average of significant unobservable inputs used to develop Level 3 fair value measurements and the narrative description of measurement uncertainty should be applied prospectively for only the most recent interim or annual period presented in the initial fiscal year of adoption. All other amendments should be applied retrospectively to all periods presented upon their effective date. Early adoption is permitted. We are in the process of evaluating the impact of the adoption of the ASU on our consolidated financial statements.

In August 2018, the FASB issued ASU No. 2018-15, Intangibles—Goodwill and Other— Internal-Use Software (Subtopic 350-40), which aligns the requirements for capitalizing implementation costs incurred in a hosting arrangement that is a service contract with the requirements for capitalizing implementation costs incurred to develop or obtain internal-use software (and hosting arrangements that include an internal use software license). The accounting for the service element of a hosting arrangement that is a service contract is not affected by the amendments in this ASU. The amendments in this Update are effective for public business entities for fiscal years beginning after December 15, 2019, and interim periods

within those fiscal years. Early adoption is permitted. We are in the process of evaluating the impact of the adoption of the ASU on our consolidated financial statements.

Revenue and Performance Obligations

12 Months Ended

Jan. 31, 2019

Revenue from Contract with Customer [Abstract]

Revenue and Performance Obligations

Subscription revenue is recognized over time and accounted for approximately 95%, 93% and 91% of our revenue in the years ended January 31, 2019, 2018 and 2017.

The typical subscription term is one to three years. Most of our subscription contracts are non-cancelable over the contractual term. Customers typically have the right to terminate their contracts for cause, if we fail to perform. As of January 31, 2019, the aggregate amount of the transaction price allocated to remaining performance obligations was $570.7 million, which consists of both billed and unbilled consideration that we expect to recognize as subscription revenue. We expect to recognize 51% of the transaction price in the twelve months following January 31, 2019, in our consolidated statement of operations and comprehensive loss with the remainder recognized thereafter.

We elected to apply the practical expedient to not disclose the transaction price allocated to remaining performance obligations for contracts with a contract term of one year or less. In addition, we do not disclose the transaction price related to revenue from professional services, training services and web revenue as revenue from these sources is recognized within one year.Contract Balances

Contract assets represent amounts for which we have recognized revenue, pursuant to our revenue recognition policy, for contracts that have not yet been invoiced to our customers where there is a remaining performance obligation, typically for multi-year arrangements. Total contract assets were $11.9 million and $16.1 million as of January 31, 2019 and 2018, of which $1.3 million and $1.9 million were noncurrent and included within "Other assets—noncurrent" on our consolidated balance sheets. The change in contract assets reflects the difference in timing between our satisfaction of remaining performance obligations and our contractual right to bill our customers.

Contract liabilities consist of deferred revenue and include payments received in advance of performance under the contract. Such amounts are generally recognized as revenue over the contractual period. In the years ended January 31, 2019, 2018 and 2017, we recognized revenue of $264.0 million, $180.4 million and $123.4 million that was included in the corresponding contract liability balance at the beginning of the periods presented.

We receive payments from customers based upon contractual billing schedules. We record accounts receivable when the right to consideration becomes unconditional. Payment terms on invoiced amounts are typically 30 days.Deferred Contract Acquisition and Fulfillment Costs

The following table represents a rollforward of our deferred contract acquisition costs:



	Year Ended January 31,
(in thousands)	2019			2018
Beginning balance	$	77,344		$	57,271
Additions to deferred contract acquisition costs	78,983			48,716
Amortization of deferred contract acquisition costs	(40,342		)	(28,643		)
Ending balance	$	115,985		$	77,344

Deferred contract acquisition costs, current	$	3,402		$	1,809
Deferred contract acquisitions costs, noncurrent	112,583			75,535
Total	$	115,985		$	77,344

The following table represents our contract fulfillment costs, which include third-party service fees:



	Year Ended January 31,
(in thousands)	2019			2018
Beginning balance	$	3,316		$	788
Additions to deferred contract fulfillment costs	1,886			4,262
Amortization of deferred contract fulfillment costs	(1,770		)	(1,734		)
Ending balance	$	3,432		$	3,316

Deferred contract fulfillment costs, current	$	765		$	1,575
Deferred contract fulfillment costs, noncurrent	2,667			1,741
Total	$	3,432		$	3,316

Current deferred contract acquisition and fulfillment costs are included in "Prepaid expenses and other current assets" and noncurrent deferred contract fulfillment costs are included in "Other assets—noncurrent" on our consolidated balance sheets.

Fair Value Measurements

12 Months Ended

Jan. 31, 2019

Fair Value Disclosures [Abstract]

Fair Value Measurements

We carry certain assets and liabilities at fair value. Fair value is defined as an exit price, representing the amount that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. The three-tier hierarchy for inputs used in measuring fair value, which prioritizes the inputs based on the observability as of the measurement date, is as follows:



Level 1	Quoted prices in active markets for identical assets or liabilities;
Level 2	Observable inputs other than the quoted prices in active markets for identical assets and liabilities; and
Level 3	Unobservable inputs for which there is little or no market data, which require us to develop assumptions of what market participants would use in pricing the asset or liability.

The following table summarizes our financial assets that are measured at fair value on a recurring basis during the period:



	January 31, 2019
(in thousands)	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses			Estimated Fair Value
Level 1:
Cash equivalents
Money market funds	$	350,063	$	—	$	—		$	350,063
Level 2:
Cash equivalents
Commercial paper	76,828		—		(11		)	76,817
Corporate notes and bonds	2,998		—		—			2,998
U.S. government agency securities	6,491		—		—			6,491
Available-for-sale securities
Commercial paper	86,655		4		(21		)	86,638
Corporate notes and bonds	287,496		389		(105		)	287,780
U.S. Treasury securities	4,982		—		(1		)	4,981
U.S. government agency securities	36,021		7		(4		)	36,024
Level 2 total	501,471		400		(142		)	501,729
Total	$	851,534	$	400	$	(142	)	$	851,792

	January 31, 2018
(in thousands)	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses			Estimated Fair Value
Level 1:
Cash equivalents
Money market funds	$	122,663	$	—	$	—		$	122,663

Money market funds consist of cash equivalents with original maturities of three months or less at the date of purchase. We use quoted prices in active markets for identical assets or liabilities to determine the fair value of our Level 1 investments in money market funds. The fair value of our Level 2 investments is determined using pricing based on quoted market prices or alternative market observable inputs.

The fair value of our available-for-sale marketable securities as of January 31, 2019, by remaining contractual maturities, were as follows (in thousands):



Due in one year or less	$	251,203
Due in one to two years	164,220
	$	415,423

As of January 31, 2019, we had a total of 119 available-for-sale securities, none of which were considered to be other-than-temporarily impaired. As of January 31, 2018, we had no marketable securities on our consolidated balance sheet.

As of January 31, 2018, our liabilities measured at fair value on recurring basis consisted of a warrant liability with a fair value $0.4 million (Level 3) for outstanding warrants to purchase 22,468 shares of our Series B-1 preferred stock. These warrants were issued in connection with a certain loan and securities agreement previously entered into with Silicon Valley Bank. We estimated the fair value of our warrant liability using the Black-Scholes pricing model. The significant unobservable inputs used in the fair value measurement of the redeemable convertible preferred stock warrant liability are the fair value of the underlying stock at the valuation date and the estimated term of the warrant. All warrants to purchase shares of convertible preferred stock converted into 22,468 warrants to purchase common stock upon the closing of our IPO

on May 1, 2018 and were exercised immediately. The related warrant liability was reclassified to additional paid-in capital as of that date. We had no liabilities measured at fair value on recurring basis as of January 31, 2019.

Convertible Senior Notes

As of January 31, 2019, the estimated fair value of our 0.5% Convertible Senior Notes with aggregate principal amount of $575.0 million equaled the principal amount. We estimated the fair value based on the quoted market prices in an inactive market on the last trading day of the reporting period (Level 2). These Convertible Senior Notes are recorded at face value less unamortized debt discount and transaction costs on our consolidated balance sheets. Refer to Note 10 for further information.

- Definition

The entire disclosure for the fair value of financial instruments (as defined), including financial assets and financial liabilities (collectively, as defined), and the measurements of those instruments as well as disclosures related to the fair value of non-financial assets and liabilities. Such disclosures about the financial instruments, assets, and liabilities would include: (1) the fair value of the required items together with their carrying amounts (as appropriate); (2) for items for which it is not practicable to estimate fair value, disclosure would include: (a) information pertinent to estimating fair value (including, carrying amount, effective interest rate, and maturity, and (b) the reasons why it is not practicable to estimate fair value; (3) significant concentrations of credit risk including: (a) information about the activity, region, or economic characteristics identifying a concentration, (b) the maximum amount of loss the entity is exposed to based on the gross fair value of the related item, (c) policy for requiring collateral or other security and information as to accessing such collateral or security, and (d) the nature and brief description of such collateral or security; (4) quantitative information about market risks and how such risks are managed; (5) for items measured on both a recurring and nonrecurring basis information regarding the inputs used to develop the fair value measurement; and (6) for items presented in the financial statement for which fair value measurement is elected: (a) information necessary to understand the reasons for the election, (b) discussion of the effect of fair value changes on earnings, (c) a description of [similar groups] items for which the election is made and the relation thereof to the balance sheet, the aggregate carrying value of items included in the balance sheet that are not eligible for the election; (7) all other required (as defined) and desired information.

+ References + Details

Property and Equipment, Net

12 Months Ended

Jan. 31, 2019

Property, Plant and Equipment [Abstract]

Property and Equipment, Net

Property and equipment consisted of the following:



	January 31,
(in thousands)	2019			2018
Computer and network equipment	$	55,233		$	54,087
Software, including capitalized software development costs	27,959			24,270
Furniture and office equipment	9,511			9,692
Leasehold improvements	41,464			37,494
	134,167			125,543
Less: Accumulated depreciation	(66,479		)	(66,160		)
	67,688			59,383
Work in progress	8,144			3,636
	$	75,832		$	63,019

As of January 31, 2019, work in progress consisted primarily of capitalized internally-developed software development costs for projects still in progress. Depreciation expense associated with property and equipment was $24.9 million, $21.7 million and $18.1 million in the years ended January 31, 2019, 2018 and 2017.

As of January 31, 2019, we capitalized $2.5 million related to the fair value of the Israel leased space and $1.7 million of construction costs in leasehold improvements under the build-to-suit lease guidance. The corresponding financing liability of $2.5 million, including interest, was recorded in "Other liabilities—noncurrent" on the consolidated balance sheets. Refer to Note 11 for additional information.

Acquisition of SpringCM Inc.

12 Months Ended

Jan. 31, 2019

Business Combinations [Abstract]

Acquisition of SpringCM Inc.

On September 4, 2018, we completed the acquisition of SpringCM Inc., or SpringCM, a cloud-based document generation and contract lifecycle management software company based in Chicago, Illinois. With the addition of SpringCM's capabilities in document generation, redlining, advanced document management and end-to-end agreement workflow, the deal further accelerates the broadening of our solution beyond e-signature to the rest of the agreement process—from preparing to signing, acting-on and managing agreements. Under the terms of the agreement, we acquired SpringCM for approximately $218.8 million in cash, excluding cash acquired, working capital and transaction cost adjustments. Of the cash paid at closing, $8.2 million will be held in escrow for an 18-month period after closing to secure our indemnification rights under the Merger Agreement.

Additionally, we granted certain continuing employees of SpringCM RSUs with service and performance conditions covering up to 0.5 million shares that will be accounted for as a post-acquisition compensation expense over the vesting period. The performance-based condition will be satisfied upon SpringCM meeting certain revenue targets. As of January 31, 2019, the performance-based condition was not considered probable.

We accounted for the transaction as a business combination using the acquisition method of accounting. We allocated the purchase price to the tangible and identifiable intangible assets acquired and liabilities assumed based on their respective estimated fair values on the acquisition date. Fair values were determined using the valuation performed by management. Excess purchase price consideration was recorded as goodwill and is primarily attributable to the assembled workforce and

expanded market opportunities when integrating SpringCM’s capabilities in document generation, redlining, advanced document management and end-to-end agreement workflow with our other offerings.

We engaged third party valuation specialists to aid our analysis of the fair value of the acquired intangibles. All estimates, key assumptions, and forecasts were either provided by or reviewed by us. While we chose to utilize a third-party valuation specialist for assistance, the fair value analysis and related valuations reflect the conclusions of management and not those of any third party.

The fair values of the assets acquired and liabilities assumed were determined using the market, income and cost approaches. The purchase price allocation was prepared on a preliminary basis and is subject to further adjustments as additional information becomes available concerning the fair value of the assets acquired and liabilities assumed. Any adjustments to the purchase price allocation will be made as soon as practicable but no later than one year from the acquisition date.

The following table summarizes the acquisition date fair values of assets acquired and liabilities assumed at the date of acquisition:



(in thousands)	September 4, 2018
Cash and cash equivalents	$	6,950
Accounts receivable and other assets	10,542
Property and equipment	6,108
Goodwill	159,097
Intangible assets	73,000
Contract liabilities	(9,973		)
Other liabilities	(12,948		)
Deferred tax liability	(7,047		)
	$	225,729

None of the goodwill recognized upon acquisition is deductible for U.S. federal income tax purposes.

The estimated useful lives, primarily based on the expected period of benefit to us, and fair values of the identifiable intangible assets at acquisition date were as follows:



(in thousands, except years)	Estimated Fair Value		Expected Useful Life
Existing technology	$	11,900	3 years
Customer relationships—subscription	54,200		9 years
Backlog—subscription	6,400		2 years
Tradenames / trademarks	500		1 year
Total preliminary intangible assets	$	73,000

In the year ended January 31, 2019, we incurred acquisition costs of $1.8 million. These costs include legal, accounting fees and other costs directly related to the acquisition and are classified within operating expenses in our consolidated statements of operations.

We included the results of operations of SpringCM in our consolidated statements of operations from the acquisition date. In the year ended January 31, 2019, our consolidated statement of operations includes revenues of $9.8 million. Due to the continued integration of the combined businesses, the information needed to determine earnings was unavailable.

The following unaudited pro forma information has been prepared for illustrative purposes only and assumes the acquisition occurred on February 1, 2017. It includes pro forma adjustments related to the amortization of acquired intangible assets, stock-based compensation expense, professional services revenue and contract acquisitions costs adjustments under the new revenue recognition standard, and contract liabilities fair value adjustment. The unaudited pro forma results have been prepared based on estimates and assumptions, which we believe are reasonable, however, they are not necessarily indicative of the consolidated results of operations had the acquisition occurred on February 1, 2017, or of future results of operations:



	(Unaudited)
	Year Ended January 31,
(in thousands, except per share data)	2019			2018
Revenue	$	720,321		$	544,680
Net loss	(459,895		)	(69,078		)
Net loss per share attributable to common stockholders, basic and diluted	(3.40		)	(2.18		)

Goodwill and Intangible Assets, Net

12 Months Ended

Jan. 31, 2019

Goodwill and Intangible Assets Disclosure [Abstract]

Goodwill and Intangible Assets, Net

The changes in the carrying amount of goodwill were as follows (in thousands):



Balance at January 31, 2017	$	35,782
Additions	139
Foreign currency translation	1,385
Balance at January 31, 2018	37,306
Additions—SpringCM	159,097
Foreign currency translation	(1,178		)
Balance at January 31, 2019	$	195,225

Intangible assets consisted of the following:



		January 31, 2019							January 31, 2018
(in thousands)	Weighted-average Remaining Useful Life (Years)	Estimated Fair Value		Accumulated Amortization			Acquisition-related Intangibles, Net		Estimated Fair Value		Accumulated Amortization			Acquisition-related Intangibles, Net
Existing technology	2.6	$	31,594	$	(20,747	)	$	10,847	$	19,694	$	(15,953	)	$	3,741
Tradenames / trademarks	0.9	2,419		(1,858		)	561		1,919		(1,294		)	625
Customer contracts & related relationships	8.3	65,782		(11,168		)	54,614		11,582		(6,411		)	5,171
Certifications	1.5	6,917		(4,846		)	2,071		6,917		(3,462		)	3,455
Maintenance contracts & related relationships	1.3	1,498		(1,104		)	394		1,498		(804		)	694
Backlog—Subscription	1.7	6,400		(1,304		)	5,096		—		—			—
	6.7	$	114,610	$	(41,027	)	73,583		$	41,610	$	(27,924	)	13,686
Cumulative translation adjustment							620							462
Total							$	74,203						$	14,148

Amortization of finite-lived intangible assets in the years ended January 31, 2019, 2018 and 2017 was classified as follows:



	Year Ended January 31,
(in thousands)	2019		2018		2017
Cost of subscription revenue	$	6,081	$	6,793	$	6,940
Sales and marketing	7,021		3,250		3,385
Total	$	13,102	$	10,043	$	10,325

As of January 31, 2019, future amortization of finite-lived intangibles that will be recorded in cost of revenue and operating expenses is estimated as follows, excluding cumulative translation adjustment (in thousands):



Fiscal 2020	$	17,717
Fiscal 2021	13,818
Fiscal 2022	8,370
Fiscal 2023	6,023
Fiscal 2024	6,023
Thereafter	21,632
Total	$	73,583

Balance Sheet Components

12 Months Ended

Jan. 31, 2019

Organization, Consolidation and Presentation of Financial Statements [Abstract]

Balance Sheet Components

Components of prepaid expenses and other current assets were as follows:



	January 31,
(in thousands)	2019		2018
Prepaid expenses and other current assets
Prepaid expenses	$	18,415	$	16,062
Other current assets	11,561		7,287
Total	$	29,976	$	23,349

Contract Balances

12 Months Ended

Jan. 31, 2019

Revenue from Contract with Customer [Abstract]

Contract Balances

Revenue and Performance Obligations

Subscription revenue is recognized over time and accounted for approximately 95%, 93% and 91% of our revenue in the years ended January 31, 2019, 2018 and 2017.

The typical subscription term is one to three years. Most of our subscription contracts are non-cancelable over the contractual term. Customers typically have the right to terminate their contracts for cause, if we fail to perform. As of January 31, 2019, the aggregate amount of the transaction price allocated to remaining performance obligations was $570.7 million, which consists of both billed and unbilled consideration that we expect to recognize as subscription revenue. We expect to recognize 51% of the transaction price in the twelve months following January 31, 2019, in our consolidated statement of operations and comprehensive loss with the remainder recognized thereafter.

We elected to apply the practical expedient to not disclose the transaction price allocated to remaining performance obligations for contracts with a contract term of one year or less. In addition, we do not disclose the transaction price related to revenue from professional services, training services and web revenue as revenue from these sources is recognized within one year.Contract Balances

Contract assets represent amounts for which we have recognized revenue, pursuant to our revenue recognition policy, for contracts that have not yet been invoiced to our customers where there is a remaining performance obligation, typically for multi-year arrangements. Total contract assets were $11.9 million and $16.1 million as of January 31, 2019 and 2018, of which $1.3 million and $1.9 million were noncurrent and included within "Other assets—noncurrent" on our consolidated balance sheets. The change in contract assets reflects the difference in timing between our satisfaction of remaining performance obligations and our contractual right to bill our customers.

Contract liabilities consist of deferred revenue and include payments received in advance of performance under the contract. Such amounts are generally recognized as revenue over the contractual period. In the years ended January 31, 2019, 2018 and 2017, we recognized revenue of $264.0 million, $180.4 million and $123.4 million that was included in the corresponding contract liability balance at the beginning of the periods presented.

We receive payments from customers based upon contractual billing schedules. We record accounts receivable when the right to consideration becomes unconditional. Payment terms on invoiced amounts are typically 30 days.Deferred Contract Acquisition and Fulfillment Costs

The following table represents a rollforward of our deferred contract acquisition costs:



	Year Ended January 31,
(in thousands)	2019			2018
Beginning balance	$	77,344		$	57,271
Additions to deferred contract acquisition costs	78,983			48,716
Amortization of deferred contract acquisition costs	(40,342		)	(28,643		)
Ending balance	$	115,985		$	77,344

Deferred contract acquisition costs, current	$	3,402		$	1,809
Deferred contract acquisitions costs, noncurrent	112,583			75,535
Total	$	115,985		$	77,344

The following table represents our contract fulfillment costs, which include third-party service fees:



	Year Ended January 31,
(in thousands)	2019			2018
Beginning balance	$	3,316		$	788
Additions to deferred contract fulfillment costs	1,886			4,262
Amortization of deferred contract fulfillment costs	(1,770		)	(1,734		)
Ending balance	$	3,432		$	3,316

Deferred contract fulfillment costs, current	$	765		$	1,575
Deferred contract fulfillment costs, noncurrent	2,667			1,741
Total	$	3,432		$	3,316

Current deferred contract acquisition and fulfillment costs are included in "Prepaid expenses and other current assets" and noncurrent deferred contract fulfillment costs are included in "Other assets—noncurrent" on our consolidated balance sheets.

Deferred Contract Acquisition and Fulfillment Costs

12 Months Ended

Jan. 31, 2019

Revenue from Contract with Customer [Abstract]

Deferred Contract Acquisition and Fulfillment Costs

Revenue and Performance Obligations

Subscription revenue is recognized over time and accounted for approximately 95%, 93% and 91% of our revenue in the years ended January 31, 2019, 2018 and 2017.

The typical subscription term is one to three years. Most of our subscription contracts are non-cancelable over the contractual term. Customers typically have the right to terminate their contracts for cause, if we fail to perform. As of January 31, 2019, the aggregate amount of the transaction price allocated to remaining performance obligations was $570.7 million, which consists of both billed and unbilled consideration that we expect to recognize as subscription revenue. We expect to recognize 51% of the transaction price in the twelve months following January 31, 2019, in our consolidated statement of operations and comprehensive loss with the remainder recognized thereafter.

We elected to apply the practical expedient to not disclose the transaction price allocated to remaining performance obligations for contracts with a contract term of one year or less. In addition, we do not disclose the transaction price related to revenue from professional services, training services and web revenue as revenue from these sources is recognized within one year.Contract Balances

Contract assets represent amounts for which we have recognized revenue, pursuant to our revenue recognition policy, for contracts that have not yet been invoiced to our customers where there is a remaining performance obligation, typically for multi-year arrangements. Total contract assets were $11.9 million and $16.1 million as of January 31, 2019 and 2018, of which $1.3 million and $1.9 million were noncurrent and included within "Other assets—noncurrent" on our consolidated balance sheets. The change in contract assets reflects the difference in timing between our satisfaction of remaining performance obligations and our contractual right to bill our customers.

Contract liabilities consist of deferred revenue and include payments received in advance of performance under the contract. Such amounts are generally recognized as revenue over the contractual period. In the years ended January 31, 2019, 2018 and 2017, we recognized revenue of $264.0 million, $180.4 million and $123.4 million that was included in the corresponding contract liability balance at the beginning of the periods presented.

We receive payments from customers based upon contractual billing schedules. We record accounts receivable when the right to consideration becomes unconditional. Payment terms on invoiced amounts are typically 30 days.Deferred Contract Acquisition and Fulfillment Costs

The following table represents a rollforward of our deferred contract acquisition costs:



	Year Ended January 31,
(in thousands)	2019			2018
Beginning balance	$	77,344		$	57,271
Additions to deferred contract acquisition costs	78,983			48,716
Amortization of deferred contract acquisition costs	(40,342		)	(28,643		)
Ending balance	$	115,985		$	77,344

Deferred contract acquisition costs, current	$	3,402		$	1,809
Deferred contract acquisitions costs, noncurrent	112,583			75,535
Total	$	115,985		$	77,344

The following table represents our contract fulfillment costs, which include third-party service fees:



	Year Ended January 31,
(in thousands)	2019			2018
Beginning balance	$	3,316		$	788
Additions to deferred contract fulfillment costs	1,886			4,262
Amortization of deferred contract fulfillment costs	(1,770		)	(1,734		)
Ending balance	$	3,432		$	3,316

Deferred contract fulfillment costs, current	$	765		$	1,575
Deferred contract fulfillment costs, noncurrent	2,667			1,741
Total	$	3,432		$	3,316

Current deferred contract acquisition and fulfillment costs are included in "Prepaid expenses and other current assets" and noncurrent deferred contract fulfillment costs are included in "Other assets—noncurrent" on our consolidated balance sheets.

Convertible Senior Notes

12 Months Ended

Jan. 31, 2019

Debt Disclosure [Abstract]

Convertible Senior Notes

In September 2018, we issued $575.0 million aggregate principal amount of 0.5% Convertible Senior Notes due in 2023 (the Notes), including the initial purchasers’ exercise in full of their option to purchase an additional $75.0 million principal amount of the Notes, in a private placement to qualified institutional buyers exempt from registration under the Securities Act. The net proceeds from the issuance of the Notes were $560.8 million after deducting the initial purchasers’ discounts and transaction costs.

The Notes are governed by an indenture (the “Indenture”) between us, as the issuer, and U.S. Bank National Association, as trustee. The Notes are our senior unsecured obligations and rank senior in right of payment to any of our indebtedness that is expressly subordinated in right of payment to the Notes; equal in right of payment to any of our unsecured indebtedness then existing and future liabilities that are not so subordinated; effectively junior in right of payment to any of our secured indebtedness, to the extent of the value of the assets securing such indebtedness; and structurally junior to all indebtedness and other liabilities (including trade payables) of our subsidiaries. The Indenture does not contain any financial covenants or restrictions on the payments of dividends, the incurrence of indebtedness, or the issuance or repurchase of securities by us or any of our subsidiaries. The Notes mature on September 15, 2023 unless earlier repurchased or redeemed by us or earlier converted in accordance with their terms prior to the maturity date. Interest is payable semi-annually in arrears on March 15 and September 15 of each year, beginning on March 15, 2019.

The Notes have an initial conversion rate of 13.9860 shares of our common stock per $1,000 principal amount of Notes, which is equal to an initial conversion price of approximately $71.50 per share of our common stock and is subject to adjustment in some events. Following certain corporate events that occur prior to the maturity date or following our issuance of a notice of redemption, we will increase the conversion rate for a holder who elects to convert its Notes in connection with

such corporate event or during the related redemption period in certain circumstances. Additionally, upon the occurrence of a corporate event that constitutes a “fundamental change” per the Indenture, holders of the Notes may require us to repurchase for cash all or a portion of their Notes at a purchase price equal to 100% of the principal amount of the Notes plus accrued and unpaid interest.

On or after June 15, 2023, until the close of business on September 13, 2023, holders may convert all or any portion of their Notes at any time regardless of whether the conditions set forth below have been met. Upon conversion, holders will receive cash, shares of our common stock or a combination of cash and shares of our common stock, at our election.

Holders of the Notes may convert all or any portion of their Notes at any time prior to the close of business on June 14, 2023, in integral multiples of $1,000 principal amount, only under the following circumstances:

•

During any fiscal quarter commencing after the fiscal quarter ended January 31, 2019 (and only during such fiscal quarter), if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding fiscal quarter is greater than or equal to 130% of the conversion price on each applicable trading day;


•	During the 5-business day period after any 10 consecutive trading day period (the “measurement period”) in which the trading price as defined in the Indenture per $1,000 principal amount of notes for each trading day of the measurement period was less than 98% of the product of the last reported sale price of our common stock and the conversion rate on each such trading day;


•	If we call any or all of the notes for redemption, at any time prior to the close of business on the scheduled trading day immediately preceding the redemption date; or


•	Upon the occurrence of specified corporate events described in the Indenture.

We may redeem for cash or shares all or any portion of the Notes, at our option, at a redemption price equal to 100% of the principal amount of the notes to be redeemed, plus accrued and unpaid interest, beginning on or after September 20, 2021 if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding fiscal quarter is greater than or equal to 130% of the conversion price on each applicable trading day.

As of January 31, 2019, the conditions allowing holders of the Notes to convert have not been met and therefore the Notes are not yet convertible.

We account for the Notes as separate liability and equity components. We determined the carrying amount of the liability component as the present value of its cash flows using a discount rate of 6% based on comparable convertible transactions for similar companies. The carrying amount of the equity component representing the conversion option was $134.7 million and was calculated by deducting the carrying value of the liability component from the principal amount of the Notes as a whole. This difference represents a debt discount that is amortized to interest expense over the term of the Notes using the effective interest rate method. The equity component is not remeasured as long as it continues to meet the conditions for equity classification.

We allocate transaction costs related to the issuance of the Notes to the liability and equity components using the same proportions as the initial carrying value of the Notes. Transaction costs attributable to the liability component were $10.9 million and are being amortized to interest expense using the effective interest method over the term of the Notes. Transaction costs attributable to the equity component were $3.3 million and are netted with the equity component of the Notes in stockholders’ equity.

The net carrying value of the liability component of the Notes was as follows:



(in thousands)	January 31, 2019
Principal	$	575,000
Less: unamortized debt discount	(125,872		)
Less: unamortized transaction costs	(10,196		)
Net carrying amount	$	438,932

The net carrying amount of the equity component of the Notes was as follows:



(in thousands)	January 31, 2019
Proceeds allocated to the conversion option (debt discount)	$	134,667
Less: transaction costs	(3,336		)
Net carrying amount	$	131,331

The interest expense recognized related to the Notes was as follows:



(in thousands)	Year Ended January 31, 2019
Contractual interest expense	$	1,071
Amortization of debt discount	8,795
Amortization of transaction costs	712
Total	$	10,578

Capped Calls

In connection with the offering of the Notes, we entered into privately-negotiated capped call transactions, or Capped Calls, with certain counterparties. The Capped Calls each have an initial strike price of approximately $71.50 per share, subject to certain adjustments, which corresponds to the initial conversion price of the Notes. The Capped Calls have initial cap prices of $110.00 per share, subject to certain adjustments. The Capped Calls cover, subject to anti-dilution adjustments, approximately 8.0 million shares of our common stock. The Capped Calls are generally intended to reduce or offset the potential dilution to our common stock upon any conversion of the Notes with such reduction or offset, as the case may be, subject to a cap based on the cap price. As the Capped Call transactions are considered indexed to our own stock and are considered equity classified, they are recorded in stockholders’ equity and are not accounted for as derivatives. The cost of $67.6 million incurred in connection with the Capped Calls was recorded as a reduction to additional paid-in capital.

Impact on Earnings Per Share

The Notes will not have an impact on our diluted earnings per share until the average market price of our common stock exceeds the conversion price of $110.00 per share, as we intend and have the ability to settle the principal amount of the Notes in cash upon conversion. We are required under the treasury stock method to compute the potentially dilutive shares of common stock related to the Notes for periods we report net income. However, upon conversion, there will be no economic dilution from the Notes until the average market price of our common stock exceeds the cap price of $110.00 per share, as exercise of the Capped Calls offsets any dilution from the Notes from the conversion price up to the cap price. Capped Calls are excluded from the calculation of diluted earnings per share, as they would be antidilutive under the treasury stock method.

Commitments and Contingencies

12 Months Ended

Jan. 31, 2019

Commitments and Contingencies Disclosure [Abstract]

Commitments and Contingencies

Operating Leases

We lease office space under noncancelable operating lease agreements that expire at various dates through June 2027. Some operating leases contain escalation provisions for adjustments in the consumer price index. We are responsible for maintenance, insurance and property taxes. We recognize rent expense on a straight-line basis over the defined lease periods. We incurred rent expense under operating leases of $19.8 million, $17.7 million and $15.8 million in the years ended January 31, 2019, 2018 and 2017. We entered into eight leases during the year ended January 31, 2019.

The future minimum annual lease payments as of January 31, 2019, related to the outstanding lease agreements were as follows (in thousands):



Fiscal 2020	$	22,198
Fiscal 2021	22,617
Fiscal 2022	22,556
Fiscal 2023	23,173
Fiscal 2024	23,373
Thereafter	34,634
Total minimum lease payments	$	148,551

Israel Build-to-Suit Lease

In July 2018, we entered into a long-term lease of a new-construction office space in Giv'at Shmuel, Israel. The lease has a term of 10 years with an option to cancel after five years and six months and an option to extend for five years. Since the office space was delivered to us as a cold shell and we are performing construction activities, for accounting purposes only, we are deemed to be the owner of the entire project, including the office space shell. In August 2018, upon commencement of the construction, we began to capitalize the related costs, including the fair value of the office space shell, as a build-to-suit property within "Property and equipment, net" and recognize a corresponding build-to-suit lease obligation, including interest. Fair value of the office space shell was estimated at $2.5 million using comparable market prices per square foot for similar space for public real estate transactions in the surrounding area. It is a Level 2 fair value measure. As of January 31, 2019, $4.2 million was capitalized for the building and construction costs. Construction was completed on the office in December 2018 and, as such, a portion of the monthly lease payment is allocated to land rent and recorded as an operating lease expense and the non-interest portion of the amortized lease payments to the landlord related to the rent of the building is applied to reduce the build-to-suit lease obligation.

Other Obligations

As of January 31, 2019, we had unused letters of credit outstanding associated with our various operating leases totaling $9.8 million.

We have entered into certain noncancelable contractual arrangements that require future purchases of goods and services. These arrangements primarily relate to cloud infrastructure support and sales and marketing activities. As of January 31, 2019, our noncancelable contractual obligations with a remaining term of more than one year were as follows (in thousands):



Fiscal 2020	$	5,722
Fiscal 2021	4,690
Fiscal 2022	2,041
Fiscal 2023	898
Fiscal 2024	943
Thereafter	4,554
Total	$	18,848

In February 2018, subsequent to year end, we renewed a cloud-based software agreement that includes a noncancelable commitment of $15.7 million through the year ended January 31, 2022. In March 2019, we purchased an investment in a private company for $15.0 million.

Indemnification

We enter into indemnification provisions under our agreements with other companies in the ordinary course of business, including business partners, contractors and parties performing our research and development. Pursuant to these arrangements, we agree to indemnify and defend the indemnified party for certain claims and related losses suffered or incurred by the indemnified party from actual or threatened third-party claim because of our activities. The duration of these indemnification agreements is generally perpetual. The maximum potential amount of future payments we could be required to make under these indemnifications is not determinable. Historically, we have not incurred material costs to defend lawsuits or settle claims related to these indemnification agreements. As a result, we believe the fair value of these indemnification agreements is not material as of January 31, 2019 and 2018. We maintain commercial general liability insurance and product liability insurance to offset certain of our potential liabilities under these indemnification agreements.

We have entered into indemnification agreements with each of our directors and executive officers. These agreements require us to indemnify such individuals, to the fullest extent permitted by Delaware law, for certain liabilities to which they may become subject as a result of their affiliation with us.

Claims and Litigation

From time to time, we may be subject to legal proceedings, claims and litigations made against us in the ordinary course of business. We are not currently a party to any legal proceedings or are aware of any pending or threatened litigation, that would have a material adverse effect to our financial condition, results of operations, or cash flows, should such litigation be resolved unfavorably.

Stockholders' Equity

12 Months Ended

Jan. 31, 2019

Equity [Abstract]

Stockholders' Equity

Redeemable Convertible Preferred Stock

We previously issued Series A, Series A-1, Series B, Series B-1, Series C, Series D, Series E, and Series F redeemable convertible preferred stock prior to the IPO. Upon completion of the IPO, all 100.2 million shares of our convertible preferred stock automatically converted into an aggregate of 100.4 million shares of our common stock. Refer to Note 1 for further information.

Common Stock Reserved for Future Issuance

We have reserved the following shares of common stock, on an as-if converted basis, for future issuance as of January 31, 2019:



	January 31,
(in thousands)	2019	2018
Conversion of outstanding convertible preferred stock	—	100,350
Warrants to purchase preferred stock	—	22
Warrants to purchase common stock	—	18
Options issued and outstanding	13,648	19,832
RSUs outstanding	17,558	23,081
Remaining shares available for future issuance under the Equity Incentive Plans	17,519	709
Remaining shares available for future issuance under the ESPP	3,800	—
Total shares of common stock reserved	52,525	144,012

Equity Incentive Plans

We maintain three stock-based compensation plans: the 2018 Equity Incentive Plan, or the 2018 Plan, the Amended and Restated 2011 Equity Incentive Plan (“2011 Plan”) and the Amended and Restated 2003 Stock Plan, or the 2003 Plan.

Our board of directors adopted, and our stockholders approved, the 2018 Plan during the year ended January 31, 2019. The 2018 Plan went into effect in April 2018, upon the effectiveness of our IPO Registration Statement. This plan serves as a successor to the 2011 Plan and 2003 Plan and provides for the grant of stock-based awards to our employees, directors and consultants. No additional awards under the 2011 Plan or 2003 Plan will be made as of the effective date of the 2018 Plan. Outstanding awards under these two plans continue to be subject to the terms and conditions of the respective plans.

Shares available for grant under the 2011 Plan that were reserved but not issued as of the effective date of the 2018 Plan were added to the reserves of the 2018 Plan. Any shares subject to outstanding awards originally granted under the 2011 Plan that: (i) expire or terminate for any reason prior to exercise or settlement; (ii) are forfeited because of the failure to meet a contingency or condition required to vest such shares or otherwise return to the Company; or (iii) are reacquired, withheld (or not issued) to satisfy a tax withholding obligation in connection with an award or to satisfy the purchase price or exercise price of a stock award shall become available for future issuance pursuant to the 2018 Plan. The equity awards available for grant for the periods presented were as follows:



(in thousands)	Year Ended January 31, 2019
Available at beginning of fiscal year	709
Awards authorized	19,021
Options canceled/expired	393
RSUs granted	(9,255	)
RSUs cancelled	1,377
Shares withheld and retired	5,274
Available at end of fiscal year	17,519

The number of shares reserved under the 2018 Plan will automatically increase on the first day of each fiscal year, starting on February 1, 2019 and continuing through February 1, 2028, in an amount equal to (i) 5% of the total number of shares of our capital stock outstanding on January 31st of the preceding fiscal year or (ii) a lesser number of shares as determined by our board of directors. Pursuant to this automatic increase, the Compensation Committee of our Board of Directors approved an increase of 8.5 million shares reserved for issuance effective on February 1, 2019.

Stock Options

We calculated the fair value of each option award on the date of grant using the Black-Scholes option pricing model. The following weighted-average assumptions were used for the periods presented, in which options were granted:



	Year Ended January 31,
	2018	2017
Risk-free interest rate	1.86% - 2.17%	1.25% - 2.19%
Expected dividend yield	—	—
Expected life of option (in years)	6.05	6.05
Expected volatility	44.99% - 45.53%	45.77% - 48.58%

The risk-free interest rate is based on the U.S. Treasury yield curve in effect at the time of grant for the expected life of the award. Our computation of expected life was based on safe harbor rules as prescribed by the “simplified” method for estimating expected term. We have assumed a 0% dividend yield. Our computation of expected volatility is based on a calculation using the historical stock information of companies deemed comparable to us, for the period matching the expected term of each option and with an end date matching each of the various measurement dates. Determination of these assumptions involves management’s best estimates at that time, which impact the fair value of the option calculated under the Black-Scholes methodology, and ultimately the expense that will be recognized over the life of the option.

The estimated weighted-average grant date fair value for stock options granted during the years ended January 31, 2018 and 2017 was $7.41 and $8.43 per share. The decrease in the value was primarily driven by an increase in the time-to-liquidity estimate, changes in industry trends and prices at which our common stock was transacted between third parties, such as employees, existing and outside investors. All such options were granted with an exercise price equal to the estimated fair value of our common stock at the date of grant. There were no options granted during the year ended January 31, 2019.

Option activity was as follows:



(in thousands, except per share data)	Number of Options Outstanding		Weighted-Average Exercise Price Per Share		Weighted-Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value (In thousands)
Balances at January 31, 2018	19,832		$	11.44	6.62	$	152,754
Options exercised	(5,791	)	9.40
Options canceled/expired	(393	)	12.36
Balances at January 31, 2019	13,648		$	12.27	5.38	$	507,371
Vested and expected to vest at January 31, 2019	13,462		$	12.20	5.35	$	501,458
Exercisable at January 31, 2019	11,548		$	11.32	4.99	$	440,309

As of January 31, 2019, our total unrecognized compensation cost related to stock option grants was $14.2 million. We expect to recognize this expense over the remaining weighted-average period of approximately 1.6 years. The aggregate intrinsic value of options exercised during the years ended January 31, 2019, 2018 and 2017 was $171.6 million, $83.6 million and $28.9 million. The total grant date fair value of options vesting during the years ended January 31, 2019, 2018 and 2017 was $25.8 million, $33.6 million and $38.8 million.

During the years ended January 31, 2018 and 2017, we modified the equity award agreements of seven employees whose employment ceased. The terms of the modification agreements accelerated the time-based vesting requirements of these employees’ unvested equity holdings and extended their time to exercise the vested stock options from the separation date. Total incremental compensation cost resulting from these modifications was $0.3 million and $4.1 million in the years ended January 31, 2018 and 2017. There were no material modifications during the year end January 31, 2019.

RSUs

Substantially all the RSUs that we have issued through January 31, 2018 vest upon the satisfaction of both service-based and performance-based vesting conditions. The service-based condition is typically satisfied over a four-year service period. The performance-based condition related to these awards was satisfied upon the effectiveness of our IPO Registration Statement on April 26, 2018. On that date we recorded a cumulative stock-based compensation expense of $262.8 million using the accelerated attribution method for all the RSUs with the service condition fully satisfied. The total grant date fair value of RSUs vested during the year ended January 31, 2019 was $260.8 million. No RSUs vested during the years ended January 31, 2018 and 2017.

During the year ended January 31, 2019, we granted 0.7 million RSUs that are subject to either a performance-based or market-based vesting conditions and a service-based condition. The performance-based conditions will be satisfied if our financial performance meets certain operating targets. The market-based conditions will be satisfied if certain milestones based on our common stock price are met. All other RSUs granted after January 31, 2018 vest on the satisfaction of a service-based condition only. The weighted-average grant date fair value for RSUs granted during the years ended January 31, 2019, 2018 and 2017 was $53.77, $17.04 and $18.04 per share.

RSU activity was as follows:



(in thousands, except per share data)	Number of Units		Weighted-Average Grant Date Fair Value
Unvested at January 31, 2018	23,081		$	17.54
Granted	9,255		53.77
Vested	(13,817	)	18.87
Canceled	(1,377	)	26.59
Unvested at January 31, 2019	17,142		$	34.56

During the year ended January 31, 2019, we settled 12.6 million RSUs for which the service-based condition was satisfied on or prior to December 15, 2018 and 0.8 million PSUs for which the performance condition was satisfied in January 2019. In connection with these settlements, we withheld 5.3 million shares and remitted tax liabilities of $215.3 million on behalf of the RSUs holders to the relevant tax authorities in cash.

As of January 31, 2019, our total unrecognized compensation cost related to RSUs was $384.5 million. We expect to recognize this expense over the remaining weighted-average period of approximately 2.1 years.

2018 Employee Stock Purchase Plan

In the year ended January 31, 2019, our board of directors adopted, and our stockholders approved the 2018 Employee Stock Purchase Plan (“2018 ESPP”). In April 2018, the 2018 ESPP went into effect upon the effectiveness of our IPO Registration Statement. Subject to any limitations contained therein, the 2018 ESPP allows eligible employees to contribute, normally through payroll deductions, up to 15% of their earnings for the purchase of our common stock at a discounted price per share. The 2018 ESPP provides for separate six-month offering periods. The initial offering period will run from September 15, 2018 through March 14, 2019.

We calculated the fair value of the ESPP purchase right using the Black‑Scholes option‑pricing model, based on the following assumptions:



	Year Ended January 31, 2019
Risk-free interest rate	2.33	%
Expected dividend yield	—	%
Expected life of purchase right (in years)	0.5
Expected volatility	40	%

The expected term for the ESPP purchase rights is estimated using the offering period, which is typically six months. We estimate volatility for options and ESPP purchase rights using volatilities of a group of public companies in a similar industry, stage of life cycle, and size. The interest rate is derived from government bonds with a similar term to the ESPP purchase right granted. We have not declared, nor do we expect to declare dividends. The weighted-average grant date fair value of ESPP purchase rights was $14.24 per share and compensation expense related to the ESPP was $2.9 million in the year ended January 31, 2019.

A total of 3.8 million shares of common stock were reserved for issuance under the 2018 ESPP. As of January 31, 2019, no shares of our common stock have been purchased under the 2018 ESPP. The number of shares reserved under the 2018 ESPP will automatically increase on the first day of each fiscal year, starting on February 1, 2019 and continuing through February 1, 2028, in an amount equal to the lesser of (i) 1% of the total number of shares of our common stock outstanding on January 31 of the preceding fiscal year, (ii) 3.8 million shares, or (iii) a lesser number of shares determined by our board of directors.

Net Loss per Share Attributable to Common Stockholders

12 Months Ended

Jan. 31, 2019

Earnings Per Share [Abstract]

Net Loss per Share Attributable to Common Stockholders

The following table presents the calculation of basic and diluted net loss per share attributable to common stockholders for periods presented:



	Year Ended January 31,
(in thousands, except per share data)	2019			2018			2017
Numerator:
Net loss	$	(426,458	)	$	(52,276	)	$	(115,412	)
Less: preferred stock accretion	(353		)	(1,461		)	(1,456		)
Net loss attributable to common stockholders	$	(426,811	)	$	(53,737	)	$	(116,868	)
Denominator:
Weighted-average common shares outstanding	135,163			32,294			28,020
Net loss per share attributable to common stockholders:
Basic and diluted	$	(3.16	)	$	(1.66	)	$	(4.17	)

Outstanding potentially dilutive securities that were excluded from the diluted per share calculations because they would have been antidilutive are as follows:



	January 31,
(in thousands)	2019	2018	2017
Convertible preferred stock as-converted	—	100,350	100,350
Stock options	13,648	19,832	27,302
Warrants to purchase convertible preferred stock	—	22	22
Warrants to purchase common stock	—	18	18
RSUs	16,568	—	—
ESPP	295	—	—
Total antidilutive securities	30,511	120,222	127,692

The table above does not include 0.6 million, 23.1 million and 16.8 million RSUs outstanding as of January 31, 2019, 2018 and 2017 as these RSUs are subject to operating and stock price targets or a liquidity event performance condition that was not considered probable as of that period.

Employee Benefit Plan	12 Months Ended
Employee Benefit Plan	Jan. 31, 2018
Postemployment Benefits [Abstract]
Employee Benefit Plan	Employee Benefit Plan In 2004, we established a defined contribution savings plan (the “Plan”) that meets the requirements under Section 401(k) of the Internal Revenue Code. This Plan covers substantially all employees who meet minimum age and service requirements and allows participants to defer a portion of their annual compensation on a pre-tax basis. In the fourth quarter of fiscal 2019, we began to match 50% of each participant’s contribution up to a maximum of 6% of the participant’s base salary and commissions paid during the period. During the year ended January 31, 2019, we recognized an expense of $1.7 million related to matching contributions. We did not make any contributions in the years ended January 31, 2018 and 2017.

Income Taxes

12 Months Ended

Jan. 31, 2019

Income Tax Disclosure [Abstract]

Income Taxes

The domestic and foreign components of pre-tax loss were as follows:



	Year Ended January 31,
(in thousands)	2019			2018			2017
U.S.	$	(460,627	)	$	(54,485	)	$	(109,669	)
International	32,419			5,343			(5,387		)
Loss before income taxes	$	(428,208	)	$	(49,142	)	$	(115,056	)

The components of our income tax provision (benefit) were as follows:



	Year Ended January 31,
(in thousands)	2019			2018			2017
Current
Federal	$	—		$	37		$	—
State	413			(46		)	28
Foreign	2,838			4,139			316
Total current	3,251			4,130			344

Deferred
Federal	(7,083		)	(110		)	80
State	(2		)	15			4
Foreign	2,084			(901		)	(72		)
Total deferred	(5,001		)	(996		)	12
Provision for (benefit from) income taxes	$	(1,750	)	$	3,134		$	356

The reconciliation of the statutory federal income tax rate to our effective tax rate was as follows:



	Year Ended January 31,
(in thousands)	2019		2018		2017
U.S statutory rate	21.0	%	32.9	%	34.0	%
State taxes	3.1		10.9		—
Foreign tax rate differential	0.3		(7.3	)	(1.9	)
Stock-based compensation	17.5		38.3		(4.6	)
Change in valuation allowance	(43.6	)	28.2		(28.2	)
Overall impact of federal tax rate change from 34% to 21%	—		(121.1	)	—
Research and development credits	4.0		2.3		—
Other	(1.9	)	9.4		0.4
Effective tax rate	0.4	%	(6.4	)%	(0.3	)%

The significant components of net deferred tax balances were as follows:



	January 31,
(in thousands)	2019			2018
Deferred tax assets
Net operating loss carryforwards	$	280,835		$	115,555
Accruals and reserves	3,180			2,800
Stock-based compensation	39,334			7,846
Research and development credits	22,876			4,977
Other	10,715			11,944
Total deferred tax assets	356,940			143,122
Deferred tax liabilities
Deferred contract acquisition costs	(28,103		)	(19,234		)
Convertible debt	(29,531		)	—
Acquired intangibles	(16,766		)	(705		)
Other	(3,885		)	(5,471		)
Total deferred tax liabilities	(78,285		)	(25,410		)
Less: Valuation allowance	(282,141		)	(119,153		)
Net deferred tax liabilities	$	(3,486	)	$	(1,441	)

We account for deferred taxes under ASC 740, Income Taxes, which requires a reduction of the carrying amounts of deferred tax assets by a valuation allowance if, based on available evidence, it is more likely than not that such assets will not be realized. Accordingly, the need to establish valuation allowances for deferred tax assets is assessed periodically based on the ASC 740 more-likely-than-not realization threshold criterion. This assessment considers matters such as future reversals of existing taxable temporary differences, projected future taxable income, tax-planning strategies and results of recent operations. The evaluation of the recoverability of the deferred tax assets requires that we weigh all positive and negative evidence to reach a conclusion that it is more likely than not that all or some portion of the deferred tax assets will not be realized. The weight given to the evidence is commensurate with the extent to which it can be objectively verified. Due to our lack of U.S. earnings history, the net U.S. deferred tax assets have been fully offset by a valuation allowance. The valuation allowance increased by $163.0 million in the year ended January 31, 2019 and decreased by $13.9 million in the year ended January 31, 2018.

On December 22, 2017, the U.S. government enacted comprehensive tax legislation commonly referred to as the Tax Cuts and Jobs Act, or the Tax Act. The Tax Act significantly impacts the future ongoing U.S. corporate income tax by, among things, lowering the U.S. corporate income tax rates from 34% to 21%, providing for unlimited net operating loss carry-forward periods, and implementing a territorial tax system. The reduction of the U.S. corporate tax rate required us to remeasure our U.S. deferred tax assets and liabilities in the year ended January 31, 2018 to the newly enacted federal rate of 21%.

In December 2017, the SEC Staff issued Staff Accounting Bulletin No. 118, Income tax Accounting Implications of the Tax Cuts and Jobs Act, which allows us to record provisional amounts during a measurement period not to extend beyond one year of the enactment date. During the three months ended January 31, 2019, the amounts recorded for the Tax Act no longer remain provisional as we completed our accounting for the effect of the Tax Act within the measurement period, under the SEC guidance, which did not have a material impact on our consolidated financial statements. However, the amounts recorded for the repatriation tax, the remeasurement of deferred taxes, and our reassessment of indefinitely reinvested earnings, uncertain tax positions, and valuation allowances may be impacted by future clarification and guidance regarding available tax accounting methods and elections, earnings and profits computations, and state tax conformity to federal tax changes, among others.

Collectively, we had no foreign earnings as of January 31, 2019, and therefore were not subject to the mandatory repatriation tax provisions of the Tax Act. However, some of our foreign subsidiaries do have accumulated earnings. No deferred tax liabilities for foreign withholding taxes have been recorded relating to the earnings of our foreign subsidiaries since all such earnings are intended to be indefinitely reinvested. The amount of the unrecognized deferred tax liability associated with these earnings is immaterial.

As of January 31, 2019, we had accumulated federal and state net operating loss carryforwards of $1.1 billion and $463.8 million. Of the $1.1 billion of federal net operating losses, $105.8 million is carried forward indefinitely and is not limited to 80% of taxable income, and $612.8 million is carried forward indefinitely, but is limited to 80% of taxable income.

The remaining federal and state net operating loss carryforwards will begin to expire in 2023 and 2022. As of January 31, 2019, we also had total foreign net operating loss carryforwards of $4.9 million, which do not expire under local law.

As of January 31, 2019, we had accumulated U.S. federal and state research tax credits of $23.6 million and $6.8 million. The U.S. federal research tax credits will begin to expire in 2023. The U.S. state research tax credits do not expire.

Available net operating losses may be subject to annual limitations due to ownership change limitations provided by the Internal Revenue Code, as amended, or the Code, and similar state provisions. Under Section 382 of the Code, substantial changes in our ownership and the ownership of acquired companies may limit the amount of net operating loss carryforwards that are available to offset taxable income. We conducted an analysis through December 31, 2018, to determine whether an ownership change had occurred since inception. The analysis indicated that, because an ownership change occurred in a prior year, federal and state net operating losses were limited pursuant to IRC Section 382. This limitation has been accounted for in calculating the available net operating loss carryforwards. In the event we have subsequent changes in ownership, net operating losses and research and development credit carryovers could be limited and may expire unutilized as a result of the subsequent ownership change. The foreign jurisdictions in which we operate may have similar provisions that may limit our ability to use net operating loss carryforwards incurred by entities that we have acquired. Additional limitations on the use of these tax attributes could occur in the event of possible disputes arising in examination from various taxing authorities.

We are subject to income taxes in the U.S. (federal and state) and numerous foreign jurisdictions. Significant judgment is required in evaluating our tax positions and determining our provision for income taxes. During the ordinary course of business, there are many transactions and calculations for which the ultimate tax determination is uncertain. We establish reserves for income tax-related uncertainties based on estimates of whether, and the extent to which, additional income taxes will be due. These reserves are established when we believe that certain positions might be challenged despite our belief that our tax return positions are fully supportable. We adjust these reserves in light of changing facts and circumstances, such as the outcome of tax audits, changes in tax regulations, the outcome of relevant court cases, and other information. The provision for income taxes includes the impact of reserve provisions and changes to reserves that are considered appropriate.

A reconciliation of the beginning and ending balance of total unrecognized tax benefits was as follows:



	January 31,
(in thousands)	2019			2018
Unrecognized tax benefits balance at February 1	$	7,733		$	—
Gross decrease for tax positions of prior years	(407		)	—
Gross increase for tax positions of current year	2,407			7,733
Unrecognized tax benefits balance at January 31	$	9,733		$	7,733

A significant portion of the unrecognized tax benefit was recorded as a reduction in our gross deferred tax assets, offset by a reduction in our valuation allowance. We have net uncertain tax positions of $2.9 million and $2.5 million included in other liabilities on our consolidated balance sheet as of January 31, 2019 and 2018. There was no such liability as of January 31, 2017.

We recognize interest and penalties related to uncertain tax positions within the income tax expense line in the consolidated statements of operations. Accrued interest and penalties are included within the related tax liability line in the consolidated balance sheets. As of January 31, 2019, accrued interest or penalties related to uncertain tax positions were $0.4 million.

The income taxes we pay are subject to review by taxing jurisdictions globally. Our estimate of the potential outcome of any uncertain tax position is subject to management’s assessment of relevant risks, facts and circumstances existing at that time. However, our future results may include adjustments to estimates in the period the audits are resolved, which may impact our effective tax rate. As of January 31, 2019, the total amount of unrecognized tax benefits that would affect our effective tax rate, if recognized, would have been $2.4 million.

Our tax years from inception in 2003 through January 31, 2019, remain subject to examination by the U.S. and California, as well as various other jurisdictions. We are under examination by the Israeli Tax Authorities for the calendar years, 2013 through 2016.

We recognize valuation allowances on deferred tax assets if it is more likely than not that some or all the deferred tax assets will not be realized. The following table represents the rollforward of our valuation allowance:



	Year Ended January 31,
(in thousands)	2019			2018			2017
Beginning balance	$	119,153		$	133,029		$	103,416
Valuation allowance charged to income tax provision	201,646			56,566			45,874
Adoption of new accounting principle	—			5,610			—
Valuation allowance credited as a result of U.S. Tax Act	—			(59,520		)	—
Convertible Debt issued	(31,594		)	—			—
Acquisition of SpringCM	(7,064		)	—			—
Valuation allowance credited to income tax provision	—			(16,532		)	(16,261		)
Ending balance	$	282,141		$	119,153		$	133,029

Geographic Information

12 Months Ended

Jan. 31, 2019

Segment Reporting [Abstract]

Geographic Information

Revenue by geography is generally based on the address of the customer as specified in our master subscription agreement. Revenue by geographic area were as follows:



	Year Ended January 31,
(in thousands)	2019		2018		2017
U.S.	$	581,011	$	428,551	$	316,309
International	119,958		89,953		65,150
Total revenue	$	700,969	$	518,504	$	381,459

No single country other than the U.S. had revenue greater than 10% of total revenue in the years ended January 31, 2019, 2018 and 2017.

Our property and equipment by geographic area were as follows:



	January 31,
(in thousands)	2019		2018
U.S.	$	60,625	$	51,023
International	15,207		11,996
Total property and equipment	$	75,832	$	63,019

Summary of Significant Accounting Policies (Policies)

12 Months Ended

Jan. 31, 2019

Accounting Policies [Abstract]

Fiscal Year

Our fiscal year ends on January 31. References to fiscal 2019, for example, are to the fiscal year ended January 31, 2019.

Use of Estimates

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates.

Significant items subject to such estimates and assumptions include those related to the allocation of revenue between recognized and deferred amounts, allowance for bad debts, goodwill, intangible assets, deferred contract acquisition costs, customer benefit period, fair value of financial instruments, valuation of stock-based compensation, valuation of common stock, fair value of the liability and equity components of the convertible notes, valuation of the build-to-suit lease, and the valuation allowance for deferred income taxes.

Concentration of Credit Risk

Our financial instruments that are exposed to concentrations of credit risk consist primarily of cash, cash equivalents, marketable securities and accounts receivable. Although we deposit our cash with multiple financial institutions, the deposits, at times, may exceed federally insured limits. We have not experienced any losses on our deposits of cash and cash equivalents. Cash equivalents consist of money market funds which are invested through financial institutions in the U.S. Management believes that the institutions are financially stable and, accordingly, minimal credit risk exists.

No customer individually accounted for more than 10% of our revenues in the years ended January 31, 2019, 2018 and 2017. One of our customers accounted for 10% of our accounts receivable as of January 31, 2019 and 2018. We perform ongoing credit evaluations of our customers, do not require collateral and maintain allowances for potential credit losses on customers’ accounts when deemed necessary.

Revenue Recognition

We recognize revenue when a customer obtains control of promised services. The amount of revenue recognized reflects the consideration that we expect to be entitled to receive in exchange for these services. To achieve the core principle of this new standard, we apply the following steps:

1. Identification of the contract, or contracts, with the customer

We consider the terms and conditions of the contract and our customary business practices in identifying our contracts under ASC 606. We determine we have a contract with a customer when the contract is approved, we can identify each party’s rights regarding the services to be transferred, we can identify the payment terms for the services, we have determined the customer has the ability and intent to pay and the contract has commercial substance. At contract inception we evaluate whether two or more contracts should be combined and accounted for as a single contract and whether the combined or single contract includes more than one performance obligation. We apply judgment in determining the customer’s ability and intent to pay, which is based on a variety of factors, including the customer’s historical payment experience or, in the case of a new customer, credit and financial information pertaining to the customer.

2. Identification of the performance obligations in the contract

Performance obligations promised in a contract are identified based on the services and the products that will be transferred to the customer that are both capable of being distinct, whereby the customer can benefit from the service either on its own or together with other resources that are readily available from third parties or from us, and are distinct in the context of the contract, whereby the transfer of the services and the products is separately identifiable from other promises in the contract. Our performance obligations consist of (i) subscription services, (ii) professional services, (iii) on-premises solutions, and (iv) maintenance and support for on-premises solutions.

3. Determination of the transaction price

The transaction price is determined based on the consideration to which we expect to be entitled in exchange for transferring services to the customer. Variable consideration is included in the transaction price if, in our judgment, it is probable that a significant future reversal of cumulative revenue under the contract will not occur. None of our contracts contain a significant financing component.

4. Allocation of the transaction price to the performance obligation in the contract

If the contract contains a single performance obligation, the entire transaction price is allocated to the single performance obligation. Contracts that contain multiple performance obligations require an allocation of the transaction price to each performance obligation based on a relative standalone selling price (“SSP”).

5. Recognition of the revenue when, or as, we satisfy a performance obligation

Revenue is recognized at the time the related performance obligation is satisfied by transferring the control of the promised service to a customer. Revenue is recognized as control of the service is transferred to the customer, in an amount that reflects the consideration that we expect to receive in exchange for those services. We generate all our revenue from contracts with customers.

Subscription Revenue

We generate revenue primarily from sales of subscriptions to access our software suite and related subscriptions of our customers. Our subscription revenue is driven by our go-to-market model, which includes a combination of direct sales, partner-assisted sales and web-based self-service purchasing. Subscription arrangements with customers do not provide the customer with the right to take possession of our software operating our software suite at any time. Instead, customers are granted continuous access to our software suite over the contractual period. A time-elapsed method is used to measure progress because we transfer control evenly over the contractual period. Accordingly, the fixed consideration related to subscription revenue is generally recognized on a straight-line basis over the contract term beginning on the date access to our software suite is provided, as long as other revenue recognition criteria have been met.

The typical subscription term is one to three years. Most of our contracts are non-cancelable over the contractual term. Customers typically have the right to terminate their contracts for cause if we fail to perform in accordance with the contractual terms. Some of our customers have the option to purchase additional subscription services at a stated price. These options are evaluated on a case-by-case basis but generally do not provide a material right as they are priced at or above our SSP and, as such, would not result in a separate performance obligation.

Professional Services and Other Revenue

Professional services and other revenue consists of fees associated with consulting and training services from assisting customers in implementing and expanding the use of our software suite. These services are distinct from subscription services. Professional services do not result in significant customization of the subscription service. Revenue from professional services provided on a time and materials basis is recognized as the services are performed. Other revenue includes amounts derived from the sale of our on-premises solutions, which are recognized upon passage of control, which occurs upon shipment of the product. The maintenance and support on the on-premises solutions is a stand-ready obligation to perform this service over the term of the arrangement and, as a result, is accounted for ratably over the term of the arrangement.

Contracts with Multiple Performance Obligations

Most of our contracts with customers contain multiple performance obligations that are distinct and accounted for separately. The transaction price is allocated to the separate performance obligations on a relative SSP basis. We determine SSP for all our performance obligations using observable inputs, such as standalone sales and historical contract pricing. SSP is consistent with our overall pricing objectives, taking into consideration the type of subscription services and professional and other services. SSP also reflects the amount we would charge for that performance obligation if it were sold separately in a standalone sale, and the price we would sell to similar customers in similar circumstances.

Variable Consideration

Revenue from sales is recorded at the net sales price, which is the transaction price, and includes estimates of variable consideration. The amount of variable consideration that is included in the transaction price is constrained and is included in the net sales price only to the extent that it is probable that a significant reversal in the amount of the cumulative revenue will not occur when the uncertainty is resolved.

If our services do not meet certain service level commitments, our customers are entitled to receive service credits, and in certain cases, refunds, each representing a form of variable consideration. We have historically not experienced any significant incidents affecting the defined levels of reliability and performance as required by our subscription contracts. Accordingly, the amount of any estimated refunds related to these agreements in the consolidated financial statements is not material during the periods presented.

Deferred Contract Acquisition Costs

We capitalize sales commissions, certain parts of the company bonus and associated payroll taxes paid to internal sales personnel that are incremental to the acquisition of customer contracts. These costs are recorded as deferred contract acquisition costs on the consolidated balance sheets. We determine whether costs should be deferred based on our sales compensation plans, if the commissions are in fact incremental and would not have occurred absent the customer contract.

Sales commissions for renewal of a subscription contract are not considered commensurate with the commissions paid for the acquisition of the initial subscription contract given the substantive difference in commission rates between new and renewal

contracts. Commissions paid upon the initial acquisition of a contract are amortized over an estimated period of benefit of five years while commissions paid related to renewal contracts are amortized over an estimated period of benefit of two years. Amortization is recognized on a straight-line basis commensurate with the pattern of revenue recognition.

Commissions paid on professional services are typically amortized in accordance with the associated revenue as the commissions paid on new and renewal professional services are commensurate with each other. We determine the period of benefit for commissions paid for the acquisition of the initial subscription contract by taking into consideration our initial estimated customer life and the technological life of our software suite and related significant features. We determine the period of benefit for renewal subscription contracts by considering the average contractual term for renewal contracts. Amortization of deferred contract acquisition costs is primarily included in the “Sales and marketing” expense in the consolidated statements of operations and comprehensive loss.

We periodically review these deferred costs to determine whether events or changes in circumstances have occurred that could impact the period of benefit of these deferred contract acquisition costs. There were no material impairment losses recorded during the periods presented.

Deferred Contract Fulfillment Costs

We capitalize third-party costs to fulfill contracts with a customer in “Prepaid expenses and other current assets” and “Other assets—noncurrent” on our consolidated balance sheets. We amortize these costs consistent with the ratable revenue recognition of the performance obligations in the associated contracts. We assess these costs for impairment at the end of each reporting period.

Cost of Revenue

“Subscription” cost of revenue primarily consists of personnel and related costs to support our software suite, amortization expense associated with capitalized internally developed software and intangible assets, property and equipment depreciation, allocated overhead expenses, merchant processing fees and server hosting costs.

“Professional services and other” cost of revenue consists primarily of personnel costs for our professional services delivery team, travel-related costs and allocated overhead.

Advertising

Advertising costs are expensed as incurred and are included in “Sales and marketing” expense in our consolidated statements of operations and comprehensive loss.