Cover Page - USD ($) $ in Billions	12 Months Ended
Cover Page - USD ($) $ in Billions	Jan. 31, 2020	Feb. 28, 2020	Jul. 31, 2019
Cover [Abstract]
Document Annual Report	true
Document Period End Date	Jan. 31, 2020
Document Transition Report	false
Entity File Number	001-38465
Entity Registrant Name	DOCUSIGN, INC.
Entity Incorporation, State or Country Code	DE
Entity Tax Identification Number	91-2183967
Entity Address, Address Line One	221 Main St.
Entity Address, Address Line Two	Suite 1550
Entity Address, City or Town	San Francisco
Entity Address, State or Province	CA
Entity Address, Postal Zip Code	94105
City Area Code	415
Local Phone Number	489-4940
Title of 12(b) Security	Common Stock, par value $0.0001 per share
Trading Symbol	DOCU
Security Exchange Name	NASDAQ
Entity Well-known Seasoned Issuer	Yes
Entity Voluntary Filers	No
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Large Accelerated Filer
Entity Small Business	false
Entity Emerging Growth Company	false
Entity Shell Company	false
Entity Public Float			$ 8.6
Entity Common Stock, Shares Outstanding		181,456,115
Entity Central Index Key	0001261333
Current Fiscal Year End Date	--01-31
Document Fiscal Year Focus	2020
Document Fiscal Period Focus	FY
Amendment Flag	false
Document Type	10-K
Documents Incorporated by Reference	Portions of the definitive proxy statement for our 2020 Annual Meeting of Stockholders are incorporated by reference in Part III of this Form 10-K. We intend to file such proxy statement with the Securities and Exchange Commission (" the SEC"), within 120 days of the fiscal year ended January 31, 2020.

Consolidated Balance Sheets - USD ($) $ in Thousands	Jan. 31, 2020	Jan. 31, 2019
Current assets
Cash and cash equivalents	$ 241,203	$ 517,811
Investments—current	414,939	251,203
Restricted cash	280	367
Accounts receivable	237,841	174,548
Contract assets—current	12,502	10,616
Prepaid expenses and other current assets	37,125	29,976
Total current assets	943,890	984,521
Investments—noncurrent	239,729	164,220
Property and equipment, net	128,293	75,832
Operating lease right-of-use assets	149,833	0
Goodwill	194,882	195,225
Intangible assets, net	56,500	74,203
Deferred contract acquisition costs—noncurrent	153,333	112,583
Other assets—noncurrent	24,678	8,833
Total assets	1,891,138	1,615,417
Current liabilities
Accounts payable	28,144	19,590
Accrued expenses and other current liabilities	54,344	35,658
Accrued compensation	83,189	77,553
Contract liabilities—current	507,560	381,060
Operating lease liabilities—current	20,728	0
Deferred rent—current	0	2,452
Total current liabilities	693,965	516,313
Convertible senior notes, net	465,321	438,932
Contract liabilities—noncurrent	11,478	7,712
Operating lease liabilities—noncurrent	162,432	0
Deferred rent—noncurrent	0	24,195
Deferred tax liability—noncurrent	4,920	4,207
Other liabilities—noncurrent	6,695	9,696
Total liabilities	1,344,811	1,001,055
Commitments and contingencies (Note 12)
Stockholders’ equity
Additional paid-in capital	1,685,167	1,545,088
Accumulated other comprehensive loss	(1,673)	(1,965)
Accumulated deficit	(1,137,185)	(928,778)
Total stockholders’ equity (deficit)	546,327	614,362
Total liabilities, redeemable convertible preferred stock, and stockholders’ equity (deficit)	1,891,138	1,615,417
Preferred Stock, Value, Outstanding	0	0
Common Stock, Value, Outstanding	$ 18	$ 17

Consolidated Balance Sheets (Parenthetical) - $ / shares	Jan. 31, 2020	Jan. 31, 2019
Statement of Financial Position [Abstract]
Common stock, par value (in usd per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	500,000,000	500,000,000
Common stock, shares outstanding (in shares)	181,254,000	169,303,000
Preferred stock, par value (in usd per share)	$ 0.0001	$ 0.0001
Preferred stock, shares authorized (in shares)	10,000,000	10,000,000
Preferred stock, shares outstanding (in shares)	0	0

Consolidated Statements of Operations and Comprehensive Loss - USD ($) shares in Thousands, $ in Thousands	12 Months Ended
	Jan. 31, 2020	Jan. 31, 2019	Jan. 31, 2018
Revenue:
Total revenue	$ 973,971	$ 700,969	$ 518,504
Cost of revenue:
Total cost of revenue	243,234	192,421	118,273
Gross profit	730,737	508,548	400,231
Operating expenses:
Sales and marketing	591,379	539,606	277,930
Research and development	185,552	185,968	92,428
General and administrative	147,315	209,297	81,526
Total operating expenses	924,246	934,871	451,884
Loss from operations	(193,509)	(426,323)	(51,653)
Interest expense	(29,254)	(10,844)	(624)
Interest income and other income, net	19,207	8,959	3,135
Loss before provision for (benefit from) income taxes	(203,556)	(428,208)	(49,142)
Provision for (benefit from) income taxes	4,803	(1,750)	3,134
Net loss	$ (208,359)	$ (426,458)	$ (52,276)
Net loss per share attributable to common stockholders, basic and diluted (in usd per share)	$ (1.18)	$ (3.16)	$ (1.66)
Weighted-average number of shares used in computing net loss per share attributable to common stockholders, basic and diluted (in shares)	176,704	135,163	32,294
Other comprehensive income (loss):
Foreign currency translation gains (losses), net of tax	$ (573)	$ (5,626)	$ 6,149
Unrealized gains on investments, net of tax	865	258	0
Other comprehensive income (loss)	292	(5,368)	6,149
Comprehensive loss	(208,067)	(431,826)	(46,127)
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	206,404	410,978	29,747
Sales and marketing
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	94,863	172,115	9,386
Research and development
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	43,211	74,108	4,896
General and administrative
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	39,745	122,715	13,578
Subscription
Revenue:
Total revenue	918,463	663,657	484,581
Cost of revenue:
Total cost of revenue	163,931	117,764	83,834
Subscription \| Cost of revenue
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	12,882	16,182	911
Professional services and other
Revenue:
Total revenue	55,508	37,312	33,923
Cost of revenue:
Total cost of revenue	79,303	74,657	34,439
Professional services and other \| Cost of revenue
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	$ 15,703	$ 25,858	$ 976

Consolidated Statement of Redeemable Convertible Preferred Stock and Stockholders' Equity (Deficit) - USD ($) shares in Thousands, $ 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, 2017		29,439
Beginning balance at Jan. 31, 2017	$ (347,355)	$ 3	$ 105,432	$ (2,746)	$ (450,044)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)		6,261
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
Ending balance at Jan. 31, 2018	(338,648)	$ 4	160,265	3,403	(502,320)
Beginning balance (in shares) at Jan. 31, 2017						100,226
Beginning balance at Jan. 31, 2017						$ 546,040
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
Ending balance at Jan. 31, 2018						$ 547,501
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)		5,791
Exercise of stock options	50,211		50,211
Settlement of RSUs (in shares)		8,126
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
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
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
Net loss	(426,458)				(426,458)
Other comprehensive income, net	(5,368)			(5,368)
Ending balance (in shares) at Jan. 31, 2019		169,303
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)
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
Ending balance at Jan. 31, 2019						$ 0
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)	6,737	6,737
Exercise of stock options	$ 72,177	$ 1	72,176
Settlement of RSUs (in shares)		4,706
Settlement of RSUs	0
Tax withholding on RSU settlement	(166,504)		(166,504)
Employee stock purchase plan (in shares)		508
Employee stock purchase plan	23,872		23,872
Employee stock-based compensation expense	210,535		210,535
Conversion of preferred stock warrant to common stock warrant in connection with initial public offering	800
Net loss	(208,359)				(208,359)
Other comprehensive income, net	292			292
Ending balance (in shares) at Jan. 31, 2020		181,254
Ending balance at Jan. 31, 2020	546,327	$ 18	$ 1,685,167	$ (1,673)	$ (1,137,185)
Increase (Decrease) in Temporary Equity [Roll Forward]
Accretion of preferred stock	$ 0

Consolidated Statements of Cash Flows - USD ($) $ in Thousands	12 Months Ended
	Jan. 31, 2020	Jan. 31, 2019	Jan. 31, 2018
Cash flows from operating activities:
Net loss	$ (208,359)	$ (426,458)	$ (52,276)
Adjustments to reconcile net loss to net cash used in operating activities
Depreciation and amortization	50,182	38,027	31,750
Amortization of deferred contract acquisition and fulfillment costs	69,747	42,112	30,377
Amortization of debt discount and transaction costs	26,389	9,507	0
Non-cash operating lease costs	19,435	0	0
Stock-based compensation expense	206,404	410,978	29,747
Deferred income taxes	1,287	(5,001)	(996)
Other	(1,741)	800	(1,877)
Changes in operating assets and liabilities
Accounts receivable	(63,293)	(42,571)	(28,077)
Contract assets	(1,508)	4,204	(6,934)
Prepaid expenses and other current assets	(3,142)	(3,283)	(1,507)
Deferred contract acquisition and fulfillment costs	(115,723)	(80,869)	(52,978)
Other assets	1,538	2,658	(1,604)
Accounts payable	3,849	(7,380)	2,864
Accrued expenses and other liabilities	9,353	6,449	9,548
Accrued compensation	5,636	26,039	9,168
Contract liabilities	130,266	100,874	87,774
Operating lease liabilities	(14,624)	0	0
Net cash provided by operating activities	115,696	76,086	54,979
Cash flows from investing activities:
Purchases of marketable securities	(861,252)	(415,132)	0
Maturities of marketable securities	627,309	0	0
Purchases of strategic investments	(15,500)	0	0
Cash paid for acquisition, net of acquired cash	0	(218,779)	(299)
Purchases of property and equipment	(72,046)	(30,413)	(18,929)
Proceeds from sale of business held for sale	0	0	467
Net cash used in investing activities	(321,489)	(664,324)	(18,761)
Cash flows from financing activities:
Proceeds from issuance of convertible senior notes, net of initial purchasers' discounts and transaction costs	0	560,756	0
Purchase of capped calls related to issuance of convertible senior notes	0	(67,563)	0
Proceeds from issuance of common stock in initial public offering, net of underwriting commissions	0	529,305	0
Payment of tax withholding obligation on RSU settlement	(166,504)	(215,332)	0
Proceeds from exercise of stock options	72,177	50,211	26,433
Proceeds from employee stock purchase plan	23,872	0	0
Payment of deferred offering costs	0	(4,011)	(315)
Other financing	0	(250)	(390)
Net cash provided by (used in) financing activities	(70,455)	853,116	25,728
Effect of foreign exchange on cash, cash equivalents and restricted cash	(447)	(4,136)	4,246
Net increase (decrease) in cash, cash equivalents and restricted cash	(276,695)	260,742	66,192
Cash, cash equivalents and restricted cash at beginning of period	518,178	257,436	191,244
Cash, cash equivalents and restricted cash at end of period	241,483	518,178	257,436
Supplemental disclosure:
Cash paid for interest	2,852	204	599
Cash paid for operating lease liabilities	22,034	0	0
Cash paid for taxes	1,970	3,213	617
Non-cash investing and financing activities:
Property and equipment in accounts payable and accrued expenses and other current liabilities	14,082	2,293	3,967
Conversion of redeemable convertible preferred stock to common stock in connection with initial public offering	0	547,854	0
Conversion of preferred stock warrant to common stock warrant in connection with initial public offering	0	848	0
Preferred stock accretion	0	353	1,461
Recognition of build-to-suit lease	0	2,479	0
Operating lease right-of-use assets exchanged for lease obligations	77,391	0	0
Derecognition of build-to-suit lease	2,479	0	0
Deferred offering costs accrued and unpaid	$ 0	$ 0	$ 1,381

Summary of Significant Accounting Policies

12 Months Ended

Jan. 31, 2020

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. All intercompany accounts and transactions have been eliminated in consolidation. The accompanying consolidated financial statements have been prepared in accordance with United States (“U.S.”) generally accepted accounting principles (“GAAP”). Our fiscal year ends on January 31. References to fiscal 2020, for example, are to the fiscal year ended January 31, 2020.

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 (“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 approximately 22 thousand 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 in the consolidated financial statements and notes thereto.

Significant items subject to such estimates and assumptions made by management include, but are not limited to, the determination of:

•the fair value of assets acquired and liabilities assumed for business combinations;

•the average period of benefit associated with deferred contract acquisition and fulfillment costs;

•the valuation of strategic investments;

•the fair value of certain stock awards issued;

•the fair value of the liability and equity components of convertible notes;

•the useful life and recoverability of long-lived assets; and

•the recognition, measurement and valuation of deferred income taxes.

The World Health Organization declared in March 2020 that the recent outbreak of the coronavirus disease named COVID-19 constitutes a pandemic. We have undertaken measures to protect our employees, partners and customers. There can be no assurance that these measures will be effective, however, or that we can adopt them without adversely affecting our business operations. In addition, the coronavirus outbreak has created and may continue to create significant uncertainty in global financial markets, which may decrease technology spending, depress demand for our solutions and harm our business and results of operations. As of the date of issuance of the financial statements, we are not aware of any specific event or circumstance that would require us to update our estimates, judgments or revise the carrying value of our assets or liabilities. These estimates may change, as new events occur and additional information is obtained, and are recognized in the consolidated financial statements as soon as they become known. Actual results could differ from those estimates and any such differences may be material to our financial statements.

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, 2020, 2019 and 2018. One of our customers accounted for 9% and 10% of our accounts receivable as of January 31, 2020 and 2019. 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. We apply significant judgment in identifying and evaluating any terms and conditions in contracts which may impact revenue recognition. 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 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.

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 generally 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 our performance obligations based on our 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.

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 as deferred contract acquisition costs in "Prepaid expenses and other current assets" and "Deferred contract acquisition costs—noncurrent" on our 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.

These deferred commissions are amortized on a straight-line basis over the periods of benefit, commensurate with the pattern of revenue recognition. Commissions paid 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. The period of benefit for commissions paid for the acquisition of the initial subscription contract, of five years, is determined by taking into consideration our initial estimated customer life and the technological life of our software suite and related significant features. The period of benefit for renewal subscription contracts, of two years, is determined by considering the average contractual term for renewal contracts.

Commissions paid on professional services contracts are amortized over the period of benefit, being the period the associated revenue is earned as the commissions paid on new and renewal professional services contracts are commensurate with each other.

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 on a straight-line basis consistent with the ratable revenue recognition of the performance obligations in the associated contracts.

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 technology-related 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 $41.6 million, $34.1 million and $19.3 million in the years ended January 31, 2020, 2019 and 2018.

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.

Stock-Based Compensation

Compensation cost for stock-based awards issued to employees, including stock options, ESPP purchase rights and restricted stock units (“RSUs”), is measured at fair value on the date of grant and recognized over the service period, generally on a straight-line basis.

The fair value of stock options and ESPP purchase rights is estimated on the date of grant using a Black-Scholes option-pricing model. The fair value of RSUs is estimated on the date of grant based on the fair value of our underlying common stock. From time to time, we grant RSUs that also include performance-based or market-based conditions. For RSUs granted with a market condition, we use a lattice model simulation analysis to value the RSUs.

Compensation expense for RSUs granted prior to January 31, 2018, is recognized 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 (“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.

Compensation expense for RSUs granted with a market or a performance condition is recognized on a graded vesting basis over the requisite service period. The amount of compensation expense related to the RSUs granted with a performance condition is determined after assessing the probability of achieving requisite performance criteria.

We recognize compensation expense related to shares issued pursuant to the 2018 Employee Stock Purchase Plan (“ESPP”) on a straight-line basis over the offering period of six months.

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.

We capitalize stock-based compensation costs incurred as a result of qualifying internally-developed software development activities.

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 use the asset and liability method of accounting for income taxes. Under this method, income tax expense is recognized for the amount of taxes payable or refundable for the current year. In addition, deferred tax assets and liabilities are recognized for expected future tax consequences of temporary differences between the financial reporting and tax basis of assets and liabilities, and for operating losses and tax credit carryforwards. We record a valuation allowance to reduce our deferred tax assets to an amount for which realization is more likely than not.

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. Monetary assets and liabilities and transactions denominated in currencies other than an entity's functional currency are remeasured into its functional currency using current exchange rates, whereas nonmonetary assets and liabilities are remeasured using historical exchange rates. We recognize gains and losses from such remeasurements within "Interest income and other income, net" in the consolidated statements of operations and comprehensive loss in the period of occurrence. We recorded foreign currency transaction losses of $1.0 million and $3.4 million for the year ended January 31, 2020 and 2019 and a foreign currency transaction gain of $2.2 million for the year ended January 31, 2018.

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 all the years presented 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

Cash and cash equivalents consist of money market funds, highly liquid investments with original maturities of three months or less at the date of purchase and deposits with financial institutions and are carried at fair value.

Investments

Investments in marketable securities consist of 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. Marketable securities 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.

Strategic Investments

Our strategic investments consist of non-marketable equity investments in privately-held companies in which we do not have a controlling interest or significant influence. We have elected to apply the measurement alternative for equity investments that do not have readily determinable fair values, measuring them at cost, less any impairment, plus or minus adjustments resulting from observable price changes in orderly transactions for the identical or a similar investment of the same issuer. An impairment loss is recorded when an event or circumstance indicates a decline in value has occurred.

In March 2019, we purchased equity investments in privately-held companies totaling $15.5 million that are classified in “Other assets—noncurrent” on our consolidated balance sheets. As there have been no material observable price changes, we have not recorded any adjustments resulting from observable price changes for identical or similar investments or impairment charges for any of our equity investments in privately-held companies in the year ended January 31, 2020. We had no such investments as of January 31, 2019.

Restricted Cash

Restricted cash 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 cash, 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 $3.0 million and $0.6 million as of January 31, 2020 and 2019. 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, and have an unconditional right to consideration prior to invoicing the customer. The unbilled accounts receivable balance was $1.6 million and $1.5 million as of January 31, 2020 and 2019.

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 all periods presented.

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.

Prior to February 1, 2019, the adoption date of Accounting Standards Update No. 2016-02, Leases (Topic 842), we were 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 recognized build-to-suit lease assets under construction and corresponding build-to-suit lease liabilities on our consolidated balance sheets. Once construction was completed, if a lease met certain “sale-leaseback” criteria, we remove the asset and liability and accounted for the lease as an operating lease. Otherwise, the lease was accounted for as a capital lease.

Leases

Leases arise from contractual obligations that convey the right to control the use of identified property, plant or equipment for a period of time in exchange for consideration. We determine whether an arrangement is or contains a lease at inception, based on whether there is an identified asset and whether we control the use of the identified asset throughout the period of use. At lease commencement date, we determine lease classification between finance and operating, allocate the consideration to the lease and nonlease components and recognize a right-of-use asset and corresponding lease liability for each lease component. A right-of-use asset represents our right to use an underlying asset and a lease liability represents our obligation to make payments during the lease term.

The lease liability is initially measured as the present value of the remaining lease payments over the lease term. The discount rate used to determine the present value is our incremental borrowing rate unless the interest rate implicit in the lease is readily determinable. We estimate our incremental borrowing rate based on the information available at lease commencement date for borrowings with a similar term. The right-of-use asset is initially measured as the present value of the lease payments, adjusted for initial direct costs, prepaid lease payments to lessors and lease incentives. Our operating lease right-of-use assets and liabilities recognized at February 1, 2019, the adoption date of Topic 842, were based on the present value of lease payments over the remaining lease term as of that date, using the incremental borrowing rate as of that date.

We do not recognize right-of-use assets and liabilities for leases with a term of twelve months or less. Additionally, we do not separate nonlease components from the associated lease components for our office leases and certain other asset classes. The total consideration includes fixed payments and contractual escalation provisions. We are responsible for maintenance, insurance, property taxes and other variable payments, which are expensed as incurred. Our leases include options to renew or terminate. We include the option to renew or terminate in our determination of the lease term when the option is deemed to be reasonably assured to be exercised.

Operating leases are classified in “Operating lease right-of-use assets”, “Operating lease liabilities—current”, and “Operating lease liabilities—noncurrent” on our consolidated balance sheets. Operating lease expense is recognized on a straight-line basis over the expected lease term and included in “Loss from operations” in our consolidated statements of operations and comprehensive loss.

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, 2020, 2019 and 2018.

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

We evaluate the estimated remaining useful lives of intangible assets and other long-lived assets to assess whether a revision to the remaining periods of amortization is required.

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. 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. There was no impairment of long-lived assets recognized in the periods presented.

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.

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.

Management’s estimates of fair value are based upon assumptions believed to be reasonable, but which are inherently uncertain. 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 our Chief Operating Decision Maker “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.

Convertible Senior Notes

In September 2018, we issued $575.0 million aggregate principal amount of 0.5% Convertible Senior Notes (the “Notes”) due 2023. 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 calculated by deducting the fair 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.

The transaction costs incurred related to the issuance of the Notes were allocated to the liability and equity components based on their relative initial carrying value of the Notes. Transaction costs attributable to the liability component are being amortized to interest expense over the respective terms of the Notes, and transaction costs attributable to the equity component are netted against the equity component of the Notes in stockholders’ equity.

The capped calls entered into in connection with the offering of the Notes 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 incurred in connection with the capped calls was recorded as a reduction to additional paid-in capital.

Legal Contingencies

We evaluate contingent liabilities including threatened or pending litigation and make provisions for such liabilities when it is both probable that a loss has been incurred and its amount can be reasonably estimated. We periodically assess the likelihood of any adverse judgments or outcomes from potential claims or legal proceedings, as well as potential ranges of probable losses, when the outcomes of the claims or proceedings are probable and reasonably estimable. A determination of the amount of the liabilities required, if any, for these contingencies is made after the analysis of each separate matter.

Recently Adopted Accounting Pronouncements

On February 1, 2019, we adopted Accounting Standards Update (“ASU”) No. 2016-02, Leases (Topic 842). We elected the optional transition approach to not apply Topic 842 in the comparative periods presented. We elected the practical expedient to use hindsight when determining the lease term and the package of practical expedients to not reassess whether existing contracts contain leases, the lease classification for existing leases and whether existing initial direct costs meet the new definition. The adoption of Topic 842 resulted in the derecognition of $26.6 million in deferred rent and the recognition of total right-of-use assets of $93.9 million and total lease liabilities of $121.8 million as of the adoption date, with the most significant impact related to our office space leases, with cumulative effect adjustment being recorded in our accumulated deficit. Additionally, we derecognized $2.5 million related to the build-to-suit asset and corresponding liability upon adoption of this standard pursuant to the transition guidance provided for build-to-suit leases. The adoption of Topic 842 did not have a material impact on our consolidated statements of operations or statements of cash flows.

On January 1, 2020, we elected to early adopt ASU No. 2019-12, Income Taxes (Topic 740): Simplifying the Accounting for Income Taxes. The ASU, which was issued by the Financial Accounting Standards Board (the "FASB") in December 2019, eliminates certain exceptions related to the general principles of Topic 740 and makes amendments to other areas with the intention of simplifying various aspects related to accounting for income taxes. The adoption of ASU 2019-12 did not have a material impact on our consolidated financial statements.

Other Recent Accounting Pronouncements

In June 2016, the FASB issued ASU No. 2016-13, Financial Instruments—Credit Losses (Topic 326). The FASB subsequently issued ASU No. 2019-04, Codification Improvements to Topic 326, Financial Instruments - Credit Losses, Topic 815, Derivatives and Hedging, and Topic 825, Financial Instruments, to eliminate inconsistencies and provide clarifications to the transition requirements of ASU No. 2016-13. These updates change 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 updates are effective for interim and annual periods beginning after December 15, 2019. The effect of adopting ASU 2016-13 and ASU 2019-04 on our consolidated financial statements and related disclosures is not expected to be material.

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 update. The update is effective for public business entities for interim and annual periods beginning after December 15, 2019. We are evaluating the impact of adoption of ASU 2018-15 on our consolidated financial statements.

Revenue and Performance Obligations

12 Months Ended

Jan. 31, 2020

Revenue from Contract with Customer [Abstract]

Revenue and Performance Obligations

Subscription revenue is recognized over time and accounted for approximately 94%, 95% and 93% of our revenue for the years ended January 31, 2020, 2019 and 2018.

As of January 31, 2020, the amount of the transaction price allocated to remaining performance obligations for contracts greater than one year was $768.7 million. We expect to recognize 53% of the transaction price allocated to remaining performance obligation within the 12 months following January 31, 2020 in our consolidated statement of operations and comprehensive loss.

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 $13.4 million and $11.9 million as of January 31, 2020 and 2019, of which $0.9 million and $1.3 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. For the years ended January 31, 2020, 2019 and 2018, we recognized revenue of $374.8 million, $264.0 million and $180.4 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 and fulfillment costs:


	Year Ended January 31,
(in thousands)	2020		2019
Deferred Contract Acquisition Costs
Beginning balance	$	115,985	$	77,344
Additions to deferred contract acquisition costs	99,382		78,983
Amortization of deferred contract acquisition costs	(58,192)		(40,342)
Cumulative translation adjustment	(1,478)		—
Ending balance	$	155,697	$	115,985

Deferred Contract Fulfillment Costs
Beginning balance	$	3,432	$	3,316
Additions to deferred contract fulfillment costs	16,341		1,886
Amortization of deferred contract fulfillment costs	(11,555)		(1,770)
Ending balance	$	8,218	$	3,432

Fair Value Measurements

12 Months Ended

Jan. 31, 2020

Fair Value Disclosures [Abstract]

Fair Value Measurements

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


	January 31, 2020
(in thousands)	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated Fair Value
Level 1:
Cash equivalents⁽¹⁾
Money market funds	$	165,424	$	—	$	—	$	165,424
Level 2:
Available-for-sale securities
Commercial paper	14,919		7		(1)		14,925
Corporate notes and bonds	372,844		891		(31)		373,704
U.S. Treasury securities	90,697		153		(1)		90,849
U.S. government agency securities	175,086		153		(49)		175,190
Level 2 total	653,546		1,204		(82)		654,668
Total	$	818,970	$	1,204	$	(82)	$	820,092

	January 31, 2019
(in thousands)	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated Fair Value
Level 1:
Cash equivalents⁽¹⁾
Money market funds	$	350,063	$	—	$	—	$	350,063
Level 2:
Cash equivalents⁽¹⁾
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

(1)Included in "cash and cash equivalents" in our consolidated balance sheets as of January 31, 2020 and 2019, in addition to cash of $75.8 million and $81.4 million

We use quoted prices in active markets for identical assets to determine the fair value of our Level 1 investments. 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 securities as of January 31, 2020, by remaining contractual maturities, were as follows (in thousands):


Due in one year or less	$	414,939
Due in one to two years	239,729
	$	654,668

As of January 31, 2020 and 2019, we had a total of 178 and 119 available-for-sale securities, none of which were considered to be other-than-temporarily impaired for the periods presented.

We had no liabilities measured at fair value on recurring basis as of January 31, 2020 and 2019.

Convertible Senior Notes

As of January 31, 2020 and 2019, the estimated fair value of our 0.5% Convertible Senior Notes with aggregate principal amount of $575.0 million was $743.5 million and $575.0 million. 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). The Notes are recorded at face value less unamortized debt discount and transaction costs as “Convertible senior notes, net” 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, 2020

Property, Plant and Equipment [Abstract]

Property and Equipment, Net

Property and equipment consisted of the following:


	January 31,
(in thousands)	2020		2019
Computer and network equipment	$	66,937	$	55,233
Software, including capitalized software development costs	33,373		27,959
Furniture and office equipment	16,752		9,511
Leasehold improvements	59,564		41,464
	176,626		134,167
Less: Accumulated depreciation	(81,228)		(66,479)
	95,398		67,688
Work in progress	32,895		8,144
	$	128,293	$	75,832

As of January 31, 2020, work in progress consisted primarily of capitalized costs of internally-developed software projects under development and leasehold improvements related to office build-out projects.

Depreciation expense associated with property and equipment was $32.5 million, $24.9 million and $21.7 million in the years ended January 31, 2020, 2019 and 2018. This included amortization expense related to capitalized internally-developed software costs of $4.1 million, $2.8 million and $3.6 million in the respective years.

We capitalized $17.1 million, $7.6 million and $2.4 million of internally developed software in the years ended January 31, 2020, 2019 and 2018. Such amounts included capitalized stock-based compensation of $4.1 million, $1.9 million and $0.1 million in the years ended January 31, 2020, 2019 and 2018.

Acquisition of SpringCM Inc.

12 Months Ended

Jan. 31, 2020

Business Combinations [Abstract]

Acquisition of SpringCM Inc.

On September 4, 2018, we completed the acquisition of SpringCM Inc. (“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 acquisition 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 merger 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 is held in escrow until 18 months after closing to partially 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 of our common stock with an aggregate grant date fair value of $26.5 million that will be accounted for as a post-acquisition compensation expense over the vesting period. The performance-based condition was partially met upon SpringCM meeting certain revenue targets for the year ended January 31, 2020.

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, using the income approach. 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.

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 was 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 intangible assets	$	73,000

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

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, 2020

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, 2018	$	37,306
Additions—SpringCM	159,097
Foreign currency translation	(1,178)
Balance at January 31, 2019	195,225
Foreign currency translation	(343)
Balance at January 31, 2020	$	194,882

Intangible assets consisted of the following:


	As of January 31, 2020													As of January 31, 2019
(in thousands, except years)	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	1.7	$	31,594	$	(25,164)	$	6,430	$	31,594	$	(20,747)	$	10,847
Tradenames / trademarks	0.3	2,419		(2,369)		50		2,419		(1,858)		561
Customer contracts & related relationships	7.5	65,782		(19,071)		46,711		65,782		(11,168)		54,614
Certifications	0.6	6,917		(6,229)		688		6,917		(4,846)		2,071
Maintenance contracts & related relationships	0.4	1,498		(1,403)		95		1,498		(1,104)		394
Backlog—Subscription	0.7	6,400		(4,508)		1,892		6,400		(1,304)		5,096
	6.5	$	114,610	$	(58,744)	55,866		$	114,610	$	(41,027)	73,583
Cumulative translation adjustment						634						620
Total						$	56,500					$	74,203

Amortization of finite-lived intangible assets was as follows:


	Year Ended January 31,
(in thousands)	2020		2019		2018
Cost of subscription revenue	$	5,704	$	6,081	$	6,793
Sales and marketing	12,013		7,021		3,250
Total	$	17,717	$	13,102	$	10,043

As of January 31, 2020, 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:


Fiscal Period	Amount (in thousands)
2021	$	13,818
2022	8,370
2023	6,023
2024	6,023
2025	6,023
Thereafter	15,609
Total	$	55,866

Balance Sheet Components

12 Months Ended

Jan. 31, 2020

Organization, Consolidation and Presentation of Financial Statements [Abstract]

Balance Sheet Components

Components of certain balance sheet line items were as follows:


	As of January 31,
(in thousands)	2020		2019
Prepaid expenses and other current assets
Prepaid expenses	$	24,429	$	18,415
Other current assets	12,696		11,561
Total	$	37,125	$	29,976

Accrued expenses and other current liabilities
Accrued expenses	$	39,350	$	21,755
Other current liabilities	14,994		13,903
Total	$	54,344	$	35,658

Contract Balances

12 Months Ended

Jan. 31, 2020

Revenue from Contract with Customer [Abstract]

Contract Balances

Revenue and Performance Obligations

Subscription revenue is recognized over time and accounted for approximately 94%, 95% and 93% of our revenue for the years ended January 31, 2020, 2019 and 2018.

As of January 31, 2020, the amount of the transaction price allocated to remaining performance obligations for contracts greater than one year was $768.7 million. We expect to recognize 53% of the transaction price allocated to remaining performance obligation within the 12 months following January 31, 2020 in our consolidated statement of operations and comprehensive loss.

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 $13.4 million and $11.9 million as of January 31, 2020 and 2019, of which $0.9 million and $1.3 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. For the years ended January 31, 2020, 2019 and 2018, we recognized revenue of $374.8 million, $264.0 million and $180.4 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 and fulfillment costs:


	Year Ended January 31,
(in thousands)	2020		2019
Deferred Contract Acquisition Costs
Beginning balance	$	115,985	$	77,344
Additions to deferred contract acquisition costs	99,382		78,983
Amortization of deferred contract acquisition costs	(58,192)		(40,342)
Cumulative translation adjustment	(1,478)		—
Ending balance	$	155,697	$	115,985

Deferred Contract Fulfillment Costs
Beginning balance	$	3,432	$	3,316
Additions to deferred contract fulfillment costs	16,341		1,886
Amortization of deferred contract fulfillment costs	(11,555)		(1,770)
Ending balance	$	8,218	$	3,432

Deferred Contract Acquisition and Fulfillment Costs

12 Months Ended

Jan. 31, 2020

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 94%, 95% and 93% of our revenue for the years ended January 31, 2020, 2019 and 2018.

As of January 31, 2020, the amount of the transaction price allocated to remaining performance obligations for contracts greater than one year was $768.7 million. We expect to recognize 53% of the transaction price allocated to remaining performance obligation within the 12 months following January 31, 2020 in our consolidated statement of operations and comprehensive loss.

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 $13.4 million and $11.9 million as of January 31, 2020 and 2019, of which $0.9 million and $1.3 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. For the years ended January 31, 2020, 2019 and 2018, we recognized revenue of $374.8 million, $264.0 million and $180.4 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 and fulfillment costs:


	Year Ended January 31,
(in thousands)	2020		2019
Deferred Contract Acquisition Costs
Beginning balance	$	115,985	$	77,344
Additions to deferred contract acquisition costs	99,382		78,983
Amortization of deferred contract acquisition costs	(58,192)		(40,342)
Cumulative translation adjustment	(1,478)		—
Ending balance	$	155,697	$	115,985

Deferred Contract Fulfillment Costs
Beginning balance	$	3,432	$	3,316
Additions to deferred contract fulfillment costs	16,341		1,886
Amortization of deferred contract fulfillment costs	(11,555)		(1,770)
Ending balance	$	8,218	$	3,432

Convertible Senior Notes

12 Months Ended

Jan. 31, 2020

Debt Disclosure [Abstract]

Convertible Senior Notes

In September 2018, we issued $575.0 million in aggregate principal amount of the Notes due in 2023, which included 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 in an offering exempt from registration under the Securities Act of 1933, as amended. 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 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. Upon conversion of the Notes, holders will receive cash, shares of our common stock or a combination of cash and shares of our common stock, at our election.

The Notes are governed by an indenture (the “Indenture”) between us, as the issuer, and U.S. Bank National Association, as trustee. 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” under 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.

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 (the "conversion conditions"):

•During any fiscal quarter commencing after the fiscal quarter ending on 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.

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 above have been met.

We may also 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, 2020, the conversion conditions have not been met and therefore the Notes are not yet convertible.

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


	January 31,
(in thousands)	2020		2019
Principal	$	575,000	$	575,000
Less: unamortized debt discount	(101,461)		(125,872)
Less: unamortized transaction costs	(8,218)		(10,196)
Net carrying amount	$	465,321	$	438,932

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


(in thousands)	January 31, 2020 and 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:


	Year Ended January 31,
(in thousands)	2020		2019
Contractual interest expense	$	2,865	$	1,071
Amortization of debt discount	24,411		8,795
Amortization of transaction costs	1,978		712
Total	$	29,254	$	10,578

Capped Calls

To minimize the potential economic dilution to our common stock upon conversion of the Notes, we entered into privately-negotiated capped call transactions ("Capped Calls") with certain counterparties and incurred costs of $67.6 million related to the transactions. 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 common stock.

Impact on Loss Per Share

In periods when we have net income, the Notes will not have an impact on our diluted earnings per share until the average market price of our common stock exceeds the initial conversion price of $71.50 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.

Leases

12 Months Ended

Jan. 31, 2020

Leases [Abstract]

Leases

We lease offices under noncancelable operating lease agreements that expire at various dates through March 2032. As of January 31, 2020, we had no finance leases. Some operating leases contain escalation provisions for adjustments in the consumer price index.

The following table is a summary of our lease costs:


(in thousands)	Year Ended January 31, 2020
Operating lease cost	$	26,490
Short-term lease cost	837
Total lease cost	$	27,327

Future lease payments under noncancelable operating leases as of January 31, 2020, were as follows:


Fiscal Period:	Amount (in thousands)
2021	$	24,327
2022	32,299
2023	32,531
2024	32,777
2025	26,307
Thereafter	67,053
Total undiscounted cash flows	$	215,294
Less: imputed interest	(32,134)
Present value of lease liabilities	$	183,160

The weighted average remaining lease term and discount rate for operating leases as of January 31, 2020 were 7.7 years and 4.4%.

We have commitments of $26.2 million, including $17.6 million entered into after January 31, 2020, for operating leases that have not yet commenced. These leases have terms of 4 to 6 years.

The future minimum annual lease payments as of January 31, 2019, prior to the adoption of Topic 842, related to the outstanding lease agreements were as follows:


Fiscal Period:	Amount (in thousands)
2020	$	22,198
2021	22,617
2022	22,556
2023	23,173
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 were 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. 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. Upon adoption of Topic 842 on February 1, 2019, we derecognized the build-to-suit asset and recognized an operating right-of-use asset for the related lease within the consolidated balance sheet as of January 31, 2020. Refer to Note 1 for additional information.

Commitments and Contingencies

12 Months Ended

Jan. 31, 2020

Commitments and Contingencies Disclosure [Abstract]

Commitments and Contingencies

As of January 31, 2020, we had unused letters of credit outstanding associated with our various operating leases totaling $10.6 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, 2020, our future noncancelable minimum payments due under these contractual obligations with a remaining term of more than one year were as follows:


Fiscal Period:	Amount (in thousands)
2021	$	13,059
2022	15,932
2023	2,988
2024	1,419
2025	990
Thereafter	3,566
Total	$	37,954

Indemnification

We enter into indemnification provisions under our agreements with customers and 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 claims 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 indemnification agreements 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, 2020 and 2019. 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, executive officers and certain other 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 litigation made against us in the ordinary course of business. We believe the final outcome of these matters will not have a material adverse effect on our business, consolidated financial position, results of operations or cash flows.

Stockholders' Equity

12 Months Ended

Jan. 31, 2020

Equity [Abstract]

Stockholders' Equity

Redeemable Convertible Preferred Stock

Prior to the IPO we issued Series A, Series A-1, Series B, Series B-1, Series C, Series D, Series E, and Series F redeemable convertible preferred stock. 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 follows:


	January 31,
(in thousands)	2020	2019
RSUs outstanding	14,246	17,558
Options issued and outstanding	6,882	13,648
Remaining shares available for future issuance under the Equity Incentive Plans	24,726	17,519
Remaining shares available for future issuance under the ESPP	4,985	3,800
Total shares of common stock reserved	50,839	52,525

Equity Incentive Plans

We maintain three stock-based compensation plans: the 2018 Equity Incentive Plan (“2018 Plan”), the Amended and Restated 2011 Equity Incentive Plan (the “2011 Plan”) and the Amended and Restated 2003 Stock Plan (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. The 2018 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 have been made since 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. Additionally, 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 returned to DocuSign, Inc.; 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 are added to the reserves of the 2018 Plan.

The 2018 Plan permits the granting of incentive stock options, nonstatutory stock options, stock appreciation rights, restricted stock awards, restricted stock unit awards, performance stock awards, performance cash awards and other stock awards. RSUs granted under the 2018 Plan generally vest over a four-year period, either quarterly or with 25% vesting at the end of one year and the remainder quarterly thereafter. Additionally, the Company grants performance-based and market-based RSUs to its executives on an annual basis.

Stock award activity was as follows:


(in thousands)			Year Ended January 31, 2020
Available at beginning of fiscal year			17,519
Awards authorized			8,570
Options canceled/expired			29
RSUs granted			(6,507)
RSUs cancelled			2,336
Shares withheld			2,779
Available at end of fiscal year			24,726

The 2018 Plan provides that the number of shares reserved will automatically increase on the first day of each fiscal year, beginning on February 1, 2019, and ending on February 1, 2028, by (i) 5% of the total number of shares of our capital stock outstanding on the immediately preceding January 31st (or such lesser number of shares as our board of directors or a committee of our board of directors may approve). The most recent automatic increase of 9.1 million shares occurred on February 1, 2020.

Stock Options

There were no options granted during the years ended January 31, 2020 and 2019. For the options granted during the year ended January 31, 2018, we calculated the fair value of each option award on the date of grant using the Black-Scholes option pricing model. We used the risk-free interest rates between 1.86% and 2.17% based on the U.S. Treasury yield curve in effect at the time of grant for the expected life of the award. We computed the expected life based on safe harbor rules as prescribed by the “simplified” method for estimating expected term, which resulted in an expected term of 6.05. We have assumed a 0% dividend yield, as we did not declare or expect to declare dividends. The expected volatility ranged between 44.99% and 45.53% 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.

The estimated weighted-average grant date fair value for stock options granted during the year ended January 31, 2018 was

$7.41 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.

Option activity was as follows:


(in thousands, except per share data and years)	Number of Options	Weighted-Average Exercise Price Per Share		Weighted-Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value
Outstanding at January 31, 2019	13,648	$	12.27	5.38	$	507,371
Exercised	(6,737)	10.09
Canceled/expired	(29)	17.67
Outstanding at January 31, 2020	6,882	$	14.39	5.38	$	441,247
Vested and expected to vest at January 31, 2020	6,836	$	14.37	5.37	$	438,502
Exercisable at January 31, 2020	6,099	$	13.98	5.17	$	393,603

As of January 31, 2020, our total unrecognized compensation cost related to stock option grants was $5.7 million. We expect to recognize this expense over the remaining weighted-average period of approximately 1 year. The aggregate intrinsic value of options exercised during the years ended January 31, 2020, 2019 and 2018 was $325.7 million, $171.6 million and $83.6 million. The total grant date fair value of options vested during the years ended January 31, 2020, 2019 and 2018 was $10.5 million, $25.8 million and $33.6 million.

RSUs

Substantially all the RSUs that we have issued on or before 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 whose service conditions were fully satisfied. The total grant date fair value of RSUs vested during the years ended January 31, 2020 and 2019 was $223.0 million and $260.8 million. No RSUs vested during the year ended January 31, 2018.

The majority of RSUs granted after January 31, 2018, vest upon the satisfaction of a service-based vesting condition. From time to time, we also grant RSUs that are subject to either a performance-based or market-based vesting condition. The performance-based conditions will be satisfied upon satisfaction of certain financial performance targets. The market-based conditions will be satisfied if certain milestones based on our common stock price or relative total shareholder return are met. The weighted-average grant date fair value for RSUs granted during the years ended January 31, 2020, 2019 and 2018 was $56.05, $53.77 and $17.04 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, 2019	17,142	$	34.56
Granted	6,507	56.05
Vested	(7,454)	29.91
Canceled	(2,336)	39.72
Unvested at January 31, 2020	13,859	$	46.28

As of January 31, 2020, our total unrecognized compensation cost related to RSUs was $465.3 million. We expect to recognize this expense over the remaining weighted-average period of approximately 2.3 years.

2018 Employee Stock Purchase Plan

During the year ended January 31, 2019, our board of directors adopted, and our stockholders approved the ESPP. In April 2018, the ESPP went into effect upon the effectiveness of our IPO Registration Statement. The ESPP allows eligible employees to purchase shares of our common stock at a discounted price by accumulating funds, normally through payroll deductions, of up to 15% of their earnings. The purchase price for common stock under the ESPP is equal to 85% of the fair market value of our common stock on the first or last day of the offering period, whichever is lower. The ESPP provides for separate six-month offering periods that begin in the first and third quarter of each year.

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,
	2020		2019
Risk-free interest rate	1.92 - 2.52 %		2.33 %
Expected dividend yield	—	%	—	%
Expected life of purchase right (in years)	0.5		0.5
Expected volatility	39 - 52 %		40 %
Weighted-average grant date fair value per share	$ 14.88 - 18.56		$ 14.24

The expected term for the ESPP purchase rights is estimated using the offering period, which is typically six months. We estimate volatility for ESPP purchase rights based on the historical volatility of our common stock price. 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. During the year ended January 31, 2020, 0.5 million shares of common stock were purchased under the ESPP. Compensation expense related to the ESPP was $8.9 million and $2.9 million for the years ended January 31, 2020 and 2019.

The number of shares reserved under the 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. As of January 31, 2020, 5.0 million shares of common stock were reserved for issuance under the ESPP.

Net Loss per Share Attributable to Common Stockholders

12 Months Ended

Jan. 31, 2020

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)	2020		2019		2018
Numerator:
Net loss	$	(208,359)	$	(426,458)	$	(52,276)
Less: preferred stock accretion	—		(353)		(1,461)
Net loss attributable to common stockholders	$	(208,359)	$	(426,811)	$	(53,737)
Denominator:
Weighted-average common shares outstanding	176,704		135,163		32,294
Net loss per share attributable to common stockholders:
Basic and diluted	$	(1.18)	$	(3.16)	$	(1.66)

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)	2020	2019	2018
RSUs	13,555	16,568	—
Stock options	6,882	13,648	19,832
ESPP	274	295	—
Convertible senior notes	788	—	—
Convertible preferred stock as-converted	—	—	100,350
Warrants to purchase convertible preferred stock	—	—	22
Warrants to purchase common stock	—	—	18
Total antidilutive securities	21,499	30,511	120,222

The table above does not include 0.3 million, 0.6 million and 23.1 million RSUs outstanding as of January 31, 2020, 2019 and 2018 as these RSUs are subject to performance-based or market-based vesting conditions that were not considered to be met or probable of being met as of the end of the reporting period.

Employee Benefit Plan	12 Months Ended
Employee Benefit Plan	Jan. 31, 2020
Postemployment Benefits [Abstract]
Employee Benefit Plan	Employee Benefit PlanWe have a qualified defined contribution plan under Section 401(k) of the Internal Revenue Code (the “Plan”). 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, 2020 and 2019, we recognized expenses of $11.0 million and $1.7 million related to matching contributions. We did not make any contributions nor recognize any related expenses in the year ended January 31, 2018.

Income Taxes

12 Months Ended

Jan. 31, 2020

Income Tax Disclosure [Abstract]

Income Taxes

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


	Year Ended January 31,
(in thousands)	2020		2019		2018
U.S.	$	(228,476)	$	(460,627)	$	(54,485)
International	24,920		32,419		5,343
Loss before income taxes	$	(203,556)	$	(428,208)	$	(49,142)

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


	Year Ended January 31,
(in thousands)	2020		2019		2018
Current
Federal	$	—	$	—	$	37
State	239		413		(46)
Foreign	3,277		2,838		4,139
Total current	3,516		3,251		4,130

Deferred
Federal	—		(7,083)		(110)
State	(43)		(2)		15
Foreign	1,330		2,084		(901)
Total deferred	1,287		(5,001)		(996)
Provision for (benefit from) income taxes	$	4,803	$	(1,750)	$	3,134

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


	Year Ended January 31,
(in thousands)	2020		2019		2018
U.S statutory rate	21.0	%	21.0	%	32.9	%
State taxes	3.5		3.1		10.9
Foreign tax rate differential	0.5		0.3		(7.3)
Stock-based compensation	47.2		17.5		38.3
Change in valuation allowance	(80.3)		(43.6)		28.2
Overall impact of federal tax rate change from 34% to 21%	—		—		(121.1)
Research and development credits	8.2		4.0		2.3
Other	(2.4)		(1.9)		9.4
Effective tax rate	(2.3)	%	0.4	%	(6.4)	%

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


	January 31,
(in thousands)	2020		2019
Deferred tax assets
Net operating loss carryforwards	$	423,379	$	280,835
Accruals and reserves	5,668		3,180
Stock-based compensation	33,405		39,334
Operating lease liability	40,495		—
Research and development credits	39,480		22,876
Other	7,536		10,715
Total deferred tax assets	549,963		356,940
Deferred tax liabilities
Operating lease right-of-use asset	(32,736)		—
Deferred contract acquisition costs	(36,567)		(28,103)
Convertible debt	(24,737)		(29,531)
Acquired intangibles	(13,493)		(16,766)
Other	(1,457)		(3,885)
Total deferred tax liabilities	(108,990)		(78,285)
Less: Valuation allowance	(445,746)		(282,141)
Net deferred tax liabilities	$	(4,773)	$	(3,486)

We intend to invest substantially all of our foreign subsidiary earnings, as well as our capital in our foreign subsidiaries, indefinitely outside of the U.S. in those jurisdictions in which we would incur significant, additional costs upon repatriation of such amounts. Therefore, no deferred tax liabilities for foreign withholding taxes have been recorded relating to the earnings of our foreign subsidiaries.

In the years ended January 31, 2020, 2019 and 2018, total stock-based compensation expense was $206.4 million, $411.0 million and $29.7 million. Recognized tax benefits on total stock-based compensation expense, which are reflected in the "Provision for (benefit from) income taxes" in the consolidated statements of operations and comprehensive loss, were $1.0 million and $1.7 million in the years ended January 31, 2020 and 2019 and immaterial in the year ended January 31, 2018.

As of January 31, 2020, we had accumulated net operating loss carryforwards of $1.7 billion for federal and $856.8 million for state. Of the federal net operating losses, $105.8 million is carried forward indefinitely and is not limited to 80% of taxable income, and $1.2 billion 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 2025 and 2021. As of January 31, 2020, we also had total foreign net operating loss carryforwards of $16.6 million, which do not expire under local law.

As of January 31, 2020, we had accumulated U.S. research tax credits of $41.0 million for federal and $10.6 million for state. The U.S. federal research tax credits will begin to expire in 2033. 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 (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. Our ability to carry forward our federal and state net operating losses is limited due to an ownership change that occurred in a prior fiscal year. This limitation has been accounted for in calculating the available net operating loss carryforwards. 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.

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


	January 31,
(in thousands)	2020		2019
Unrecognized tax benefits balance at February 1	$	9,733	$	7,733
Gross increase for tax positions of prior years	90		—
Gross decrease for tax positions of prior years	(94)		(407)
Gross increase for tax positions of current year	3,156		2,407
Unrecognized tax benefits balance at January 31	$	12,885	$	9,733

As of January 31, 2020, the total amount of unrecognized tax benefits that would affect our effective tax rate, if recognized, would have been $2.5 million. 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 $3.3 million, $2.9 million and $2.5 million included in other liabilities on our consolidated balance sheet as of January 31, 2020, 2019 and 2018.

We do not expect our gross unrecognized tax benefit to change significantly within the next 12 months. We recognize interest and penalties related to uncertain tax positions in provision for income taxes. As of January 31, 2020, accrued interest or penalties was $0.8 million.

Our tax years from inception in 2003 through January 31, 2020, 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. Due to our history of losses in the U.S., the net cumulative U.S. deferred tax assets have been fully offset by a valuation allowance. The valuation allowance increased by $163.6 million in the year ended January 31, 2020 and by $163.0 million in the year ended January 31, 2019. The following table represents the rollforward of our valuation allowance:


	Year Ended January 31,
(in thousands)	2020		2019		2018
Beginning balance	$	282,141	$	119,153	$	133,029
Valuation allowance charged to income tax provision	163,605		201,646		56,566
Adoption of new accounting principle	—		—		5,610
Valuation allowance credited as a result of U.S. Tax Act	—		—		(59,520)
Convertible senior notes issued	—		(31,594)		—
Acquisition of SpringCM	—		(7,064)		—
Valuation allowance credited to income tax provision	—		—		(16,532)
Ending balance	$	445,746	$	282,141	$	119,153

Geographic Information

12 Months Ended

Jan. 31, 2020

Segment Reporting [Abstract]

Geographic Information

We operate in one operating segment and one reportable segment as we only report financial information on an aggregate and consolidated basis to the Chief Executive Officer, who is our CODM.

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


	Year Ended January 31,
(in thousands)	2020		2019		2018
U.S.	$	802,480	$	581,011	$	428,551
International	171,491		119,958		89,953
Total revenue	$	973,971	$	700,969	$	518,504

No single country other than the U.S. had revenue greater than 10% of total revenue in the years ended January 31, 2020, 2019 and 2018.

Our long-lived assets by geographic area, which consist of property and equipment, net and operating lease right-of-use assets were as follows:


	January 31,
(in thousands)	2020		2019
U.S.	$	182,288	$	60,625
International	95,838		15,207
Total long-lived assets	$	278,126	$	75,832

Subsequent Events	12 Months Ended
Subsequent Events	Jan. 31, 2020
Subsequent Events [Abstract]
Subsequent Events	Subsequent EventsOn February 26, 2020, we entered into a Share Purchase Agreement to acquire all outstanding equity in Seal Software Group Limited, a leading contract analytics and artificial intelligence technology provider, for a purchase consideration of approximately $188.0 million in cash, subject to adjustments. The acquisition is subject to closing conditions and is expected to close in the first half of our fiscal year ending January 31, 2021.

Summary of Significant Accounting Policies (Policies)

12 Months Ended

Jan. 31, 2020

Accounting Policies [Abstract]

Consolidation

Basis of Presentation and Principles of ConsolidationOur consolidated financial statements include those of DocuSign, Inc. and our subsidiaries. All intercompany accounts and transactions have been eliminated in consolidation.

Basis of Accounting