DocuSign (DOCU) 10-Q 6 Dec 19 2020 Q3 Quarterly report Financial data

Cover Page

Cover Page - shares	9 Months Ended
	Oct. 31, 2019	Nov. 30, 2019
Cover page.
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Oct. 31, 2019
Document Transition Report	false
Entity File Number	001-38465
Entity Registrant Name	DOCUSIGN, INC.
Entity Central Index Key	0001261333
Current Fiscal Year End Date	--01-31
Amendment Flag	false
Document Fiscal Year Focus	2020
Document Fiscal Period Focus	Q3
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 Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Non-accelerated Filer
Entity Emerging Growth Company	true
Entity Small Business	false
Entity Ex Transition Period	true
Entity Shell Company	false
Entity Common Stock, Shares Outstanding		179,455,116

Condensed Consolidated Balance

Condensed Consolidated Balance Sheets (Unaudited) - USD ($) $ in Thousands	Oct. 31, 2019	Jan. 31, 2019
Current assets
Cash and cash equivalents	$ 197,697	$ 517,811
Investments—current	456,080	251,203
Restricted cash	414	367
Accounts receivable	159,464	174,548
Contract assets—current	17,921	10,616
Prepaid expense and other current assets	37,814	29,976
Total current assets	869,390	984,521
Investments—noncurrent	257,783	164,220
Property and equipment, net	105,917	75,832
Long-Lived Assets	242,544	75,832
Operating lease right-of-use assets	136,627
Goodwill	195,024	195,225
Intangible assets, net	60,759	74,203
Deferred contract acquisition costs—noncurrent	136,248	112,583
Other assets—noncurrent	24,617	8,833
Total assets	1,786,365	1,615,417
Current liabilities
Accounts payable	29,099	19,590
Accrued expenses	33,094	21,755
Accrued compensation	70,860	77,553
Contract liabilities—current	423,742	381,060
Operating lease liabilities—current	18,743
Deferred rent—current		2,452
Other liabilities—current	12,956	13,903
Total current liabilities	588,494	516,313
Convertible senior notes, net	458,578	438,932
Contract liabilities—noncurrent	9,339	7,712
Operating lease liabilities—noncurrent	150,362
Deferred rent—noncurrent		24,195
Deferred tax liability—noncurrent	4,275	4,207
Other liabilities—noncurrent	5,955	9,696
Total liabilities	1,217,003	1,001,055
Commitments and contingencies (Note 11)
Stockholders' equity
Preferred stock, $0.0001 par value; 10,000 shares authorized, 0 shares issued and outstanding as of October 31, 2019 and January 31, 2019	0	0
Common stock, $0.0001 par value; 500,000 shares authorized, 179,252 shares outstanding as of October 31, 2019; 500,000 shares authorized, 169,303 shares outstanding as of January 31, 2019	18	17
Additional paid-in capital	1,660,313	1,545,088
Accumulated other comprehensive loss	(1,191)	(1,965)
Accumulated deficit	(1,089,778)	(928,778)
Total stockholders' equity	569,362	614,362
Total liabilities and stockholders' equity	$ 1,786,365	$ 1,615,417

Condensed Consolidated Balanc_2

Condensed Consolidated Balance Sheets (Unaudited) (Parenthetical) - $ / shares	Oct. 31, 2019	Jan. 31, 2019
Statement of Financial Position [Abstract]
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 issued (in shares)	0	0
Preferred stock, shares outstanding (in shares)	0	0
Common stock, par value (in usd per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	500,000,000	500,000,000
Common stock, shares outstanding (in shares)	179,252,000	169,303,000

Condensed Consolidated Statemen

Condensed Consolidated Statements of Operations and Comprehensive Loss (Unaudited) - USD ($) shares in Thousands, $ in Thousands	3 Months Ended		9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018	Oct. 31, 2019	Oct. 31, 2018
Revenue:
Total revenue	$ 249,502	$ 178,385	$ 699,076	$ 501,237
Cost of revenue:
Total cost of revenue	61,964	45,073	175,159	139,728
Gross profit	187,538	133,312	523,917	361,509
Operating expenses:
Sales and marketing	149,231	117,051	430,053	411,915
Research and development	48,758	38,404	133,458	143,047
General and administrative	33,546	36,274	111,562	170,242
Total operating expenses	231,535	191,729	675,073	725,204
Loss from operations	(43,997)	(58,417)	(151,156)	(363,695)
Interest expense	(7,364)	(3,503)	(21,793)	(3,743)
Interest income and other income, net	5,801	3,395	15,549	4,165
Loss before provision for (benefit from) income taxes	(45,560)	(58,525)	(157,400)	(363,273)
Provision for (benefit from) income taxes	1,038	(5,712)	3,552	(3,059)
Net loss	$ (46,598)	$ (52,813)	$ (160,952)	$ (360,214)
Net loss per share attributable to common stockholders, basic and diluted	$ (0.26)	$ (0.31)	$ (0.92)	$ (2.90)
Weighted-average number of shares used in computing net loss per share attributable to common stockholders, basic and diluted	178,314	167,736	175,303	124,343
Other comprehensive income (loss):
Foreign currency translation gain (loss), net of tax	$ 1,336	$ (1,483)	$ (340)	$ (6,896)
Unrealized gains on investments, net of tax	418	0	1,114	0
Other comprehensive income (loss)	1,754	(1,483)	774	(6,896)
Comprehensive loss	(44,844)	(54,296)	(160,178)	(367,110)
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense			150,799	361,707
Sales and marketing
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	24,649	22,338	68,693	151,610
Research and development
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	11,679	9,919	30,959	64,546
General and administrative
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	9,258	13,515	30,339	109,165
Subscription
Revenue:
Total revenue	238,072	169,426	660,341	476,085
Cost of revenue:
Total cost of revenue	43,178	28,709	115,769	84,204
Subscription | Cost of revenue
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	3,534	2,398	8,931	13,941
Professional services and other
Revenue:
Total revenue	11,430	8,959	38,735	25,152
Cost of revenue:
Total cost of revenue	18,786	16,364	59,390	55,524
Professional services and other | Cost of revenue
Stock-based compensation expense included in costs and expenses:
Stock-based compensation expense	$ 3,616	$ 3,578	$ 11,877	$ 22,445

Condensed Consolidated Statem_2

Condensed Consolidated Statements of Redeemable Convertible Preferred Stock and Stockholders' Equity (Deficit) (Unaudited) - USD ($) shares in Thousands, $ in Thousands	Total	Common Stock	Additional Paid-In Capital	Accumulated Other Comprehensive Loss	Accumulated Deficit	Redeemable Convertible Preferred Stock
Beginning balance (in shares) at Jan. 31, 2018		35,700
Beginning balance at Jan. 31, 2018	$ (338,648)	$ 4	$ 160,265	$ 3,403	$ (502,320)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)		1,869
Exercise of stock options	15,365		15,365
Employee stock-based compensation expense	362,260		362,260
Non-employee stock-based compensation expense	886		886
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	525,299	$ 2	525,297
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 warrants (in shares)		22
Exercise of warrants	0
Net loss	(360,214)				(360,214)
Other comprehensive income (loss), net	(6,896)			(6,896)
Ending balance (in shares) at Oct. 31, 2018		157,255
Ending balance at Oct. 31, 2018	810,169	$ 16	1,676,180	(3,493)	(862,534)
Beginning balance (in shares) at Jan. 31, 2018						100,226
Beginning balance at Jan. 31, 2018						$ 547,501
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 Oct. 31, 2018						0
Ending balance at Oct. 31, 2018						$ 0
Beginning balance (in shares) at Jul. 31, 2018		156,786
Beginning balance at Jul. 31, 2018	743,470	$ 16	1,555,185	(2,010)	(809,721)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)		469
Exercise of stock options	5,048		5,048
Employee stock-based compensation expense	52,126		52,126
Non-employee stock-based compensation expense	53		53
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)
Net loss	(52,813)				(52,813)
Other comprehensive income (loss), net	(1,483)			(1,483)
Ending balance (in shares) at Oct. 31, 2018		157,255
Ending balance at Oct. 31, 2018	810,169	$ 16	1,676,180	(3,493)	(862,534)
Increase (Decrease) in Temporary Equity [Roll Forward]
Accretion of preferred stock	0
Ending balance (in shares) at Oct. 31, 2018						0
Ending balance at Oct. 31, 2018						$ 0
Beginning balance (in shares) at Jan. 31, 2019		169,303
Beginning balance at Jan. 31, 2019	$ 614,362	$ 17	1,545,088	(1,965)	(928,778)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)	5,746	5,746
Exercise of stock options	$ 62,263		62,263
Settlement of RSUs (in shares)		5,921
Settlement of RSUs	0	$ 1	(1)
Tax withholding on RSU settlement (in shares)		(2,226)
Tax withholding on RSU settlement	(125,288)		(125,288)
Employee stock purchase plan (in shares)		508
Employee stock purchase plan	23,872		23,872
Employee stock-based compensation expense	154,274		154,274
Non-employee stock-based compensation expense	105		105
Net loss	(160,952)				(160,952)
Other comprehensive income (loss), net	774			774
Ending balance (in shares) at Oct. 31, 2019		179,252
Ending balance at Oct. 31, 2019	569,362	$ 18	1,660,313	(1,191)	(1,089,778)
Increase (Decrease) in Temporary Equity [Roll Forward]
Accretion of preferred stock	0
Beginning balance (in shares) at Jul. 31, 2019		175,953
Beginning balance at Jul. 31, 2019	566,679	$ 18	1,612,786	(2,945)	(1,043,180)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Exercise of stock options (in shares)		1,877
Exercise of stock options	19,815		19,815
Settlement of RSUs (in shares)		1,777
Settlement of RSUs	0
Tax withholding on RSU settlement (in shares)		(632)
Tax withholding on RSU settlement	(39,310)		(39,310)
Employee stock purchase plan (in shares)		277
Employee stock purchase plan	13,309		13,309
Employee stock-based compensation expense	53,677		53,677
Non-employee stock-based compensation expense	36		36
Net loss	(46,598)				(46,598)
Other comprehensive income (loss), net	1,754			1,754
Ending balance (in shares) at Oct. 31, 2019		179,252
Ending balance at Oct. 31, 2019	569,362	$ 18	$ 1,660,313	$ (1,191)	$ (1,089,778)
Increase (Decrease) in Temporary Equity [Roll Forward]
Accretion of preferred stock	$ 0

Condensed Consolidated Statem_3

Condensed Consolidated Statements of Cash Flows (Unaudited) - USD ($) $ in Thousands	9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018
Cash flows from operating activities:
Net loss	$ (160,952)	$ (360,214)
Adjustments to reconcile net loss to net cash used in operating activities
Depreciation and amortization	36,916	26,024
Amortization of deferred contract acquisition and fulfillment costs	49,360	29,889
Amortization of debt discount and transaction costs	19,647	3,147
Non-cash operating lease costs	13,843	0
Stock-based compensation expense	150,799	361,707
Deferred income taxes	42	(7,347)
Other	(2,142)	(2,079)
Changes in operating assets and liabilities
Accounts receivable	15,084	1,366
Contract assets	(7,223)	2,774
Prepaid expenses and other current assets	(2,036)	(2,383)
Deferred contract acquisition and fulfillment costs	(77,800)	(52,545)
Other assets	926	2,002
Accounts payable	2,306	(5,990)
Accrued expenses	7,236	3,610
Accrued compensation	(6,693)	2,171
Contract liabilities	44,309	35,856
Operating lease liabilities	(10,886)	0
Other liabilities	(2,545)	3,961
Net cash provided by operating activities	70,191	41,949
Cash flows from investing activities:
Purchases of marketable securities	(753,934)	0
Maturities of marketable securities	460,710	0
Purchases of strategic investments	(15,500)	0
Cash paid for acquisition, net of acquired cash	0	(218,779)
Purchases of property and equipment	(42,071)	(19,096)
Net cash used in investing activities	(350,795)	(237,875)
Cash flows from financing activities:
Proceeds from issuance of convertible senior notes, net of initial purchasers' discounts and transaction costs	0	560,756
Purchase of capped calls related to issuance of convertible senior notes	0	(67,563)
Proceeds from issuance of common stock in initial public offering, net of underwriting commissions	0	529,305
Payment of tax withholding obligation on RSU settlement	(125,288)	0
Proceeds from exercise of stock options	62,263	15,365
Proceeds from employee stock purchase plan	23,872	0
Payment of deferred offering costs	0	(3,692)
Net cash provided by (used in) financing activities	(39,153)	1,034,171
Effect of foreign exchange on cash, cash equivalents and restricted cash	(310)	(1,181)
Net increase (decrease) in cash, cash equivalents and restricted cash	(320,067)	837,064
Cash, cash equivalents and restricted cash at beginning of period	518,178	257,436
Cash, cash equivalents and restricted cash at end of period	198,111	1,094,500
Supplemental disclosure:
Cash paid for interest	2,852	204
Cash paid for operating lease liabilities	16,313
Cash paid for taxes	1,745	2,718
Non-cash investing and financing activities:
Property and equipment in accounts payable and other accrued liabilities	13,162	4,889
Conversion of redeemable convertible preferred stock to common stock in connection with initial public offering	0	547,854
Conversion of preferred stock warrant to common stock warrant in connection with initial public offering	0	848
Preferred stock accretion	0	353
Recognition of build-to-suit lease	0	$ 2,479
Operating lease right-of-use assets exchanged for lease obligations	58,694
Derecognition of build-to-suit lease	$ 2,479

Summary of Significant Accounti

Summary of Significant Accounting Policies	9 Months Ended
	Oct. 31, 2019
Accounting Policies [Abstract]
Summary of Significant Accounting Policies	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 condensed consolidated financial statements include the accounts of DocuSign, Inc. and our subsidiaries. All intercompany transactions and balances have been eliminated in consolidation. Our condensed consolidated financial statements have been prepared in accordance with United States (“U.S.”) generally accepted accounting principles (“GAAP”) for interim financial information. Certain information and note disclosures normally included in the financial statements prepared in accordance with GAAP have been condensed or omitted pursuant to the applicable rules and regulations of the Securities and Exchange Commission (“SEC”). Therefore, these unaudited interim consolidated financial statements should be read in conjunction with the consolidated financial statements and related notes included in our 2019 Annual Report on Form 10-K. Our condensed consolidated financial statements are unaudited and have been prepared on a basis consistent with that used to prepare the audited annual consolidated financial statements and, in our opinion, include all adjustments of a normal recurring nature necessary for the fair statement of our financial position, results of operations and cash flows. Our condensed consolidated balance sheet as of January 31, 2019 was derived from audited financial statements but does not include all disclosures required by GAAP. The results of operations for the nine months ended October 31, 2019 are not necessarily indicative of the results to be expected for the year ending January 31, 2020 . Our fiscal year ends on January 31. References to fiscal 2020 , for example, are to the fiscal year ending January 31, 2020 . Use of Estimates The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates. Items subject to such estimates and assumptions include those related to the allocation of revenue between recognized and deferred amounts, allowance for bad debts, goodwill, intangible assets, deferred contract acquisition costs, customer benefit period, fair value of financial instruments, valuation of stock-based compensation, valuation of common stock, f air value of the liability and equity components of the convertible notes, whether an arrangement is or contains a lease, the discount rate used for operating leases, and the valuation allowance for deferred income taxes. Significant Accounting Policies Other than described below, there have been no changes to our significant accounting policies described in our 2019 Annual Report on Form 10-K that have had a material impact on our consolidated financial statements and related notes. 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, 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 condensed 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 condensed 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 were classified in “ Other assets—noncurrent ” on our condensed 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 nine months ended October 31, 2019 . We had no such investments as of January 31, 2019 . 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 to the consolidated statements of operations or statements of cash flows. Other Recent Accounting Pronouncements In June 2016, the Financial Accounting Standards Board (“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 ASUs 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 ASUs are effective for interim and annual periods beginning after December 15, 2019. We are evaluating the impact of the adoption of the ASUs on our consolidated financial statements. In August 2018, the FASB issued ASU No. 2018-15, Intangibles—Goodwill and Other—Internal-Use Software (Subtopic 350-40), which aligns the requirements for capitalizing implementation costs incurred in a hosting arrangement that is a service contract with the requirements for capitalizing implementation costs incurred to develop or obtain internal-use software (and hosting arrangements that include an internal use software license). The accounting for the service element of a hosting arrangement that is a service contract is not affected by the amendments in this ASU. The ASU is effective for public business entities for interim and annual periods beginning after December 15, 2019. Early adoption is permitted. We are evaluating the impact of the adoption of the ASU on our consolidated financial statements.

Fair Value Measurements

Fair Value Measurements	9 Months Ended
	Oct. 31, 2019
Fair Value Disclosures [Abstract]
Fair Value Measurements	Fair Value Measurements We carry certain assets at fair value. Fair value is defined as an exit price, representing the amount that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. The three-tier hierarchy for inputs used in measuring fair value, which prioritizes the inputs based on the observability as of the measurement date, is as follows: Level 1 Quoted prices in active markets for identical assets or liabilities; Level 2 Observable inputs other than the quoted prices in active markets for identical assets and liabilities; and Level 3 Unobservable inputs for which there is little or no market data, which require us to develop assumptions of what market participants would use in pricing the asset or liability. The following table summarizes our financial assets that are measured at fair value on a recurring basis during the period: October 31, 2019 (in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Level 1: Cash equivalents Money market funds $ 82,438 $ — $ — $ 82,438 Level 2: Available-for-sale securities Commercial paper 31,415 26 — 31,441 Corporate notes and bonds 368,440 982 (67 ) 369,355 U.S. Treasury securities 135,550 313 (3 ) 135,860 U.S. government agency securities 177,083 181 (57 ) 177,207 Level 2 total 712,488 1,502 (127 ) 713,863 Total $ 794,926 $ 1,502 $ (127 ) $ 796,301 January 31, 2019 (in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Level 1: Cash equivalents Money market funds $ 350,063 $ — $ — $ 350,063 Level 2: Cash equivalents Commercial paper 76,828 — (11 ) 76,817 Corporate notes and bonds 2,998 — — 2,998 U.S. government agency securities 6,491 — — 6,491 Available-for-sale securities Commercial paper 86,655 4 (21 ) 86,638 Corporate notes and bonds 287,496 389 (105 ) 287,780 U.S. Treasury securities 4,982 — (1 ) 4,981 U.S. government agency securities 36,021 7 (4 ) 36,024 Level 2 total 501,471 400 (142 ) 501,729 Total $ 851,534 $ 400 $ (142 ) $ 851,792 Money market funds consist of cash equivalents with original maturities of three months or less at the date of purchase. We use quoted prices in active markets for identical assets to determine the fair value of our Level 1 investments in money market funds. The fair value of our Level 2 investments is determined using pricing based on quoted market prices or alternative market observable inputs . The fair value of our available-for-sale marketable securities as of October 31, 2019 , by remaining contractual maturities, were as follows (in thousands): Due in one year or less $ 456,080 Due in one to two years 257,783 $ 713,863 As of October 31, 2019 , we had a total of 181 available-for-sale securities, none of which were considered to be other-than-temporarily impaired. Convertible Senior Notes As of October 31, 2019 , the estimated fair value of our 0.5% Convertible Senior Notes (the “Notes”) with aggregate principal amount of $575.0 million was $673.5 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 9 for further information.

Revenue and Performance Obligat

Revenue and Performance Obligations	9 Months Ended
	Oct. 31, 2019
Revenue from Contract with Customer [Abstract]
Revenue and Performance Obligations	Revenue and Performance Obligations Subscription revenue is recognized over time and accounted for approximately 95% of our revenue for both the three months ended October 31, 2019 and 2018 . It accounted for approximately 94% and 95% of our revenue for the nine months ended October 31, 2019 and 2018 . The typical subscription term is one to three years . Most of our subscription contracts are noncancelable over the contractual term. Customers typically have the right to terminate their contracts for cause, if we fail to perform. As of October 31, 2019 , the aggregate amount of the transaction price allocated to remaining performance obligations was $673.3 million , which consists of both billed and unbilled consideration that we expect to recognize as subscription revenue. We expect to recognize 54% of the transaction price in the 12 months following October 31, 2019 , in our consolidated statement of operations and comprehensive loss with the remainder recognized thereafter. We do not disclose the transaction price allocated to remaining performance obligations for contracts with a contract term of one year or less. In addition, we do not disclose the transaction price related to revenue from professional services, training services and web revenue as revenue from these sources is recognized within one year. Contract 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 $19.2 million and $11.9 million as of October 31, 2019 and January 31, 2019 , of which $1.2 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 nine months ended October 31, 2019 and 2018 , we recognized revenue of $342.6 million and $238.1 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. The following table represents a rollforward of our deferred contract acquisition costs: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 115,985 $ 77,344 Additions to deferred contract acquisition costs 66,416 51,038 Amortization of deferred contract acquisition costs (42,099 ) (28,561 ) Cumulative translation adjustment (1,188 ) — Ending balance $ 139,114 $ 99,821 October 31, (in thousands) 2019 2018 Deferred contract acquisition costs, current $ 2,866 $ 2,730 Deferred contract acquisitions costs, noncurrent 136,248 97,091 Total $ 139,114 $ 99,821 The following table represents our contract fulfillment costs, which include third-party service fees: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 3,432 $ 3,316 Additions to deferred contract fulfillment costs 11,384 1,507 Amortization of deferred contract fulfillment costs (7,261 ) (1,328 ) Ending balance $ 7,555 $ 3,495 October 31, (in thousands) 2019 2018 Deferred contract fulfillment costs, current $ 4,052 $ 1,042 Deferred contract fulfillment costs, noncurrent 3,503 2,453 Total $ 7,555 $ 3,495 Current deferred contract acquisition and fulfillment costs are included in "Prepaid expense and other current assets" and noncurrent deferred contract fulfillment costs are included in "Other assets—noncurrent" on our consolidated balance sheets.

Property and Equipment, Net

Property and Equipment, Net	9 Months Ended
	Oct. 31, 2019
Property, Plant and Equipment [Abstract]
Property and Equipment, Net	Property and Equipment, Net Property and equipment consisted of the following: (in thousands) October 31, 2019 January 31, 2019 Computer and network equipment $ 64,204 $ 55,233 Software, including capitalized software development costs 34,371 27,959 Furniture and office equipment 12,343 9,511 Leasehold improvements 48,916 41,464 159,834 134,167 Less: Accumulated depreciation (77,094 ) (66,479 ) 82,740 67,688 Work in progress 23,177 8,144 $ 105,917 $ 75,832 Depreciation expense associated with property and equipment was $8.4 million and $6.5 million for the three months ended October 31, 2019 and 2018 , and $23.5 million and $17.9 million for the nine months ended October 31, 2019 and 2018 . As of January 31, 2019 , leasehold improvements include $2.5 million related to the fair value of the Israel leased space that was recorded under the build-to-suit lease guidance. 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 condensed consolidated balance sheet as of October 31, 2019 . Refer to Note 1

Acquisition of SpringCM Inc.

Acquisition of SpringCM Inc.	9 Months Ended
	Oct. 31, 2019
Business Combinations [Abstract]
Acquisition of SpringCM Inc.	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 restricted stock units (“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 will be satisfied upon SpringCM meeting certain revenue targets during the year ending January 31, 2020, and will impact the quantity of shares that will vest. As of October 31, 2019 , the performance-based condition was considered probable of being met. We accounted for the transaction as a business combination using the acquisition method of accounting. We allocated the purchase price to the tangible and identifiable intangible assets acquired and liabilities assumed based on their respective estimated fair values on the acquisition date. Fair values were determined using the valuation performed by management. Excess purchase price consideration was recorded as goodwill and is primarily attributable to the assembled workforce and expanded market opportunities when integrating SpringCM’s capabilities in document generation, redlining, advanced document management and end-to-end agreement workflow with our other offerings. The fair values of the assets acquired and liabilities assumed were determined using the market, income and cost approaches. The following table summarizes the acquisition date fair values of assets acquired and liabilities assumed at the date of acquisition: (in thousands) September 4, 2018 Cash and cash equivalents $ 6,950 Accounts receivable and other assets 10,542 Property and equipment 6,108 Goodwill 159,097 Intangible assets 73,000 Contract liabilities (9,973 ) Other liabilities (12,948 ) Deferred tax liability (7,047 ) $ 225,729 None of the goodwill recognized upon acquisition is deductible for U.S. federal income tax purposes. The estimated useful lives, primarily based on the expected period of benefit to us, and fair values of the identifiable intangible assets at acquisition date were as follows: (in thousands, except years) Estimated Fair Value Expected Useful Life Existing technology $ 11,900 3 years Customer relationships—subscription 54,200 9 years Backlog—subscription 6,400 2 years Tradenames / trademarks 500 1 year Total 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 condensed 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: (in thousands, except per share data) Three Months Ended Nine Months Ended Revenue $ 181,490 $ 517,507 Net loss (57,433 ) (384,917 ) Net loss per share attributable to common stockholders, basic and diluted (0.34 ) (3.10 )

Goodwill and Intangible Assets,

Goodwill and Intangible Assets, Net	9 Months Ended
	Oct. 31, 2019
Goodwill and Intangible Assets Disclosure [Abstract]
Goodwill and Intangible Assets, Net	Goodwill and Intangible Assets, Net The changes in the carrying amount of goodwill for the nine months ended October 31, 2019 , were as follows (in thousands): Balance at January 31, 2019 $ 195,225 Cumulative translation adjustment (201 ) Balance at October 31, 2019 $ 195,024 Intangible assets consisted of the following: As of October 31, 2019 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 1.9 $ 31,594 $ (24,138 ) $ 7,456 $ 31,594 $ (20,747 ) $ 10,847 Tradenames / trademarks 0.5 2,419 (2,319 ) 100 2,419 (1,858 ) 561 Customer contracts & related relationships 7.7 65,782 (17,110 ) 48,672 65,782 (11,168 ) 54,614 Certifications 0.8 6,917 (5,884 ) 1,033 6,917 (4,846 ) 2,071 Maintenance contracts & related relationships 0.6 1,498 (1,328 ) 170 1,498 (1,104 ) 394 Backlog—Subscription 0.9 6,400 (3,705 ) 2,695 6,400 (1,304 ) 5,096 6.5 $ 114,610 $ (54,484 ) 60,126 $ 114,610 $ (41,027 ) 73,583 Cumulative translation adjustment 633 620 Total $ 60,759 $ 74,203 Amortization of finite-lived intangible assets for the three and nine months ended October 31, 2019 and 2018 , was as follows: Three Months Ended October 31, Nine Months Ended October 31, (in thousands) 2019 2018 2019 2018 Cost of subscription revenue $ 1,348 $ 1,632 $ 4,356 $ 4,303 Sales and marketing 2,957 2,257 9,102 3,787 Total $ 4,305 $ 3,889 $ 13,458 $ 8,090 As of October 31, 2019 , future amortization of finite-lived intangibles that will be recorded in cost of revenue and operating expenses is estimated as follows, excluding cumulative translation adjustment: Fiscal Period: (in thousands) 2020, remainder $ 4,260 2021 13,818 2022 8,370 2023 6,023 2024 6,023 Thereafter 21,632 Total $ 60,126

Contract Balances

Contract Balances	9 Months Ended
	Oct. 31, 2019
Revenue from Contract with Customer [Abstract]
Contract Balances	Revenue and Performance Obligations Subscription revenue is recognized over time and accounted for approximately 95% of our revenue for both the three months ended October 31, 2019 and 2018 . It accounted for approximately 94% and 95% of our revenue for the nine months ended October 31, 2019 and 2018 . The typical subscription term is one to three years . Most of our subscription contracts are noncancelable over the contractual term. Customers typically have the right to terminate their contracts for cause, if we fail to perform. As of October 31, 2019 , the aggregate amount of the transaction price allocated to remaining performance obligations was $673.3 million , which consists of both billed and unbilled consideration that we expect to recognize as subscription revenue. We expect to recognize 54% of the transaction price in the 12 months following October 31, 2019 , in our consolidated statement of operations and comprehensive loss with the remainder recognized thereafter. We do not disclose the transaction price allocated to remaining performance obligations for contracts with a contract term of one year or less. In addition, we do not disclose the transaction price related to revenue from professional services, training services and web revenue as revenue from these sources is recognized within one year. Contract 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 $19.2 million and $11.9 million as of October 31, 2019 and January 31, 2019 , of which $1.2 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 nine months ended October 31, 2019 and 2018 , we recognized revenue of $342.6 million and $238.1 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. The following table represents a rollforward of our deferred contract acquisition costs: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 115,985 $ 77,344 Additions to deferred contract acquisition costs 66,416 51,038 Amortization of deferred contract acquisition costs (42,099 ) (28,561 ) Cumulative translation adjustment (1,188 ) — Ending balance $ 139,114 $ 99,821 October 31, (in thousands) 2019 2018 Deferred contract acquisition costs, current $ 2,866 $ 2,730 Deferred contract acquisitions costs, noncurrent 136,248 97,091 Total $ 139,114 $ 99,821 The following table represents our contract fulfillment costs, which include third-party service fees: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 3,432 $ 3,316 Additions to deferred contract fulfillment costs 11,384 1,507 Amortization of deferred contract fulfillment costs (7,261 ) (1,328 ) Ending balance $ 7,555 $ 3,495 October 31, (in thousands) 2019 2018 Deferred contract fulfillment costs, current $ 4,052 $ 1,042 Deferred contract fulfillment costs, noncurrent 3,503 2,453 Total $ 7,555 $ 3,495 Current deferred contract acquisition and fulfillment costs are included in "Prepaid expense and other current assets" and noncurrent deferred contract fulfillment costs are included in "Other assets—noncurrent" on our consolidated balance sheets.

Deferred Contract Acquisition a

Deferred Contract Acquisition and Fulfillment Costs	9 Months Ended
	Oct. 31, 2019
Revenue from Contract with Customer [Abstract]
Deferred Contract Acquisition and Fulfillment Costs	Revenue and Performance Obligations Subscription revenue is recognized over time and accounted for approximately 95% of our revenue for both the three months ended October 31, 2019 and 2018 . It accounted for approximately 94% and 95% of our revenue for the nine months ended October 31, 2019 and 2018 . The typical subscription term is one to three years . Most of our subscription contracts are noncancelable over the contractual term. Customers typically have the right to terminate their contracts for cause, if we fail to perform. As of October 31, 2019 , the aggregate amount of the transaction price allocated to remaining performance obligations was $673.3 million , which consists of both billed and unbilled consideration that we expect to recognize as subscription revenue. We expect to recognize 54% of the transaction price in the 12 months following October 31, 2019 , in our consolidated statement of operations and comprehensive loss with the remainder recognized thereafter. We do not disclose the transaction price allocated to remaining performance obligations for contracts with a contract term of one year or less. In addition, we do not disclose the transaction price related to revenue from professional services, training services and web revenue as revenue from these sources is recognized within one year. Contract 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 $19.2 million and $11.9 million as of October 31, 2019 and January 31, 2019 , of which $1.2 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 nine months ended October 31, 2019 and 2018 , we recognized revenue of $342.6 million and $238.1 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. The following table represents a rollforward of our deferred contract acquisition costs: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 115,985 $ 77,344 Additions to deferred contract acquisition costs 66,416 51,038 Amortization of deferred contract acquisition costs (42,099 ) (28,561 ) Cumulative translation adjustment (1,188 ) — Ending balance $ 139,114 $ 99,821 October 31, (in thousands) 2019 2018 Deferred contract acquisition costs, current $ 2,866 $ 2,730 Deferred contract acquisitions costs, noncurrent 136,248 97,091 Total $ 139,114 $ 99,821 The following table represents our contract fulfillment costs, which include third-party service fees: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 3,432 $ 3,316 Additions to deferred contract fulfillment costs 11,384 1,507 Amortization of deferred contract fulfillment costs (7,261 ) (1,328 ) Ending balance $ 7,555 $ 3,495 October 31, (in thousands) 2019 2018 Deferred contract fulfillment costs, current $ 4,052 $ 1,042 Deferred contract fulfillment costs, noncurrent 3,503 2,453 Total $ 7,555 $ 3,495 Current deferred contract acquisition and fulfillment costs are included in "Prepaid expense and other current assets" and noncurrent deferred contract fulfillment costs are included in "Other assets—noncurrent" on our consolidated balance sheets.

Convertible Senior Notes

Convertible Senior Notes	9 Months Ended
	Oct. 31, 2019
Debt Disclosure [Abstract]
Convertible Senior Notes	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 governed by an indenture (the “Indenture”) between us, as the issuer, and U.S. Bank National Association, as trustee. 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. 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. On or after June 15, 2023, until the close of business on September 13, 2023, holders may convert all or any portion of their Notes at any time regardless of whether the conditions set forth below have been met. Upon conversion, holders will receive cash, shares of our common stock or a combination of cash and shares of our common stock, at our election. Holders of the Notes may convert all or any portion of their Notes at any time prior to the close of business on June 14, 2023, in integral multiples of $1,000 principal amount, only under the following circumstances: • During any fiscal quarter commencing after the fiscal quarter 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. We may redeem for cash or shares all or any portion of the Notes, at our option, at a redemption price equal to 100% of the principal amount of the notes to be redeemed, plus accrued and unpaid interest, beginning on or after September 20, 2021 if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding fiscal quarter is greater than or equal to 130% of the conversion price on each applicable trading day. As of October 31, 2019 , the conditions allowing holders of the Notes to convert have not been met and therefore the Notes are not yet convertible. We account for the Notes as separate liability and equity components. We determined the carrying amount of the liability component as the present value of its cash flows using a discount rate of 6% based on comparable convertible transactions for similar companies. The carrying amount of the equity component representing the conversion option was $134.7 million and was calculated by deducting the carrying value of the liability component from the principal amount of the Notes as a whole. This difference represents a debt discount that is amortized to interest expense over the term of the Notes using the effective interest rate method. The equity component is not remeasured as long as it continues to meet the conditions for equity classification. We allocate transaction costs related to the issuance of the Notes to the liability and equity components using the same proportions as the initial carrying value of the Notes. Transaction costs attributable to the liability component were $10.9 million and are being amortized to interest expense using the effective interest method over the term of the Notes. Transaction costs attributable to the equity component were $3.3 million and are netted with the equity component of the Notes in stockholders’ equity. The net carrying value of the liability component of the Notes was as follows: (in thousands) October 31, 2019 Principal $ 575,000 Less: unamortized debt discount (107,698 ) Less: unamortized transaction costs (8,724 ) Net carrying amount $ 458,578 The net carrying amount of the equity component of the Notes was as follows: (in thousands) October 31, 2019 Proceeds allocated to the conversion option (debt discount) $ 134,667 Less: transaction costs (3,336 ) Net carrying amount $ 131,331 The interest expense recognized related to the Notes was as follows: (in thousands) Three Months Ended October 31, 2019 Nine Months Ended October 31, 2019 Contractual interest expense $ 719 $ 2,157 Amortization of debt discount 6,147 18,175 Amortization of transaction costs 498 1,472 Total $ 7,364 $ 21,804 Capped Calls In connection with the offering of the Notes, we entered into privately-negotiated capped call transactions (“Capped Calls”) with certain counterparties. The Capped Calls each have an initial strike price of approximately $71.50 per share, subject to certain adjustments, which corresponds to the initial conversion price of the Notes. The Capped Calls have initial cap prices of $110.00 per share, subject to certain adjustments. The Capped Calls cover, subject to anti-dilution adjustments, approximately 8.0 million shares of common stock. The Capped Calls are generally intended to reduce or offset the potential dilution to our common stock upon any conversion of the Notes with such reduction or offset, as the case may be, subject to a cap based on the cap price. As the Capped Call transactions are considered indexed to our own stock and are considered equity classified, they are recorded in stockholders’ equity and are not accounted for as derivatives. The cost of $67.6 million incurred in connection with the Capped Calls was recorded as a reduction to additional paid-in capital. Impact on Earnings Per Share The Notes will not have an impact on our diluted earnings per share until the average market price of our common stock exceeds the cap price of $110.00 per share, as we intend and have the ability to settle the principal amount of the Notes in cash upon conversion. We are required under the treasury stock method to compute the potentially dilutive shares of common stock related to the Notes for periods we report net income. However, upon conversion, there will be no economic dilution from the Notes until the average market price of our common stock exceeds the cap price of $110.00 per share, as exercise of the Capped Calls offsets any dilution from the Notes from the conversion price up to the cap price. Capped Calls are excluded from the calculation of diluted earnings per share, as they would be antidilutive under the treasury stock method.

Leases

Leases	9 Months Ended
	Oct. 31, 2019
Leases [Abstract]
Leases	Leases We lease office space and equipment under non-cancelable operating lease agreements that expire at various dates through February 2032 . As of October 31, 2019 , we have no finance leases. The following table is a summary of our operating lease costs: (in thousands) Three Months Ended Nine Months Ended Operating lease cost $ 6,762 $ 19,055 Short-term lease cost 60 474 Variable lease cost and other, net (25 ) 162 Total lease cost $ 6,797 $ 19,691 Future lease payments as of October 31, 2019 , were as follows: Fiscal Period: (in thousands, except years and percentages) 2020, remainder $ 5,872 2021 27,502 2022 28,534 2023 28,978 2024 29,103 Thereafter 80,154 Total undiscounted cash flows $ 200,143 Less: imputed interest (31,038 ) Present value of lease liabilities $ 169,105 Weighted average remaining term (years) 7.9 Weighted average discount rate 4.4 % The future minimum annual lease payments as of January 31, 2019 , related to the outstanding lease agreements were as follows: Fiscal period: (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 As of October 31, 2019 , we had commitments of $ 26.2 million for operating leases with commencement dates subsequent to quarter end. These leases have terms of 8

Commitments and Contingencies

Commitments and Contingencies	9 Months Ended
	Oct. 31, 2019
Commitments and Contingencies Disclosure [Abstract]
Commitments and Contingencies	Commitments and Contingencies As of October 31, 2019 , we had unused letters of credit outstanding associated with our various operating leases totaling $9.9 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 October 31, 2019 , our noncancelable contractual obligations with a remaining term of more than one year were as follows: Fiscal period: (in thousands) 2020, remainder $ 4,097 2021 15,238 2022 12,522 2023 898 2024 943 Thereafter 4,555 Total $ 38,253 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 claim because of our activities. The duration of these indemnification agreements is generally perpetual. The maximum potential amount of future payments we could be required to make under these indemnifications is not determinable. Historically, we have not incurred material costs to defend lawsuits or settle claims related to these indemnification agreements. As a result, we believe the fair value of these indemnification agreements is not material as of October 31, 2019 , and January 31, 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 litigations 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

Stockholders' Equity	9 Months Ended
	Oct. 31, 2019
Equity [Abstract]
Stockholders' Equity	Stockholders' Equity Equity Incentive Plans We maintain three stock-based compensation plans: the 2018 Equity Incentive Plan (the “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 initial public offering (“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. 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 RSUs to its executives on an annual basis. Shares available for grant under the 2011 Plan that were reserved but not issued as of the effective date of the 2018 Plan were added to the reserves of the 2018 Plan. Any shares subject to outstanding awards originally granted under the 2011 Plan that: (i) expire or terminate for any reason prior to exercise or settlement; (ii) are forfeited because of the failure to meet a contingency or condition required to vest such shares or otherwise 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 will be added to the reserves of the 2018 Plan. As of October 31, 2019 , 24.5 million shares were available for future issuance under the 2018 Plan. 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 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 8.5 million shares occurred on February 1, 2019. Stock Options Option activity for the nine months ended October 31, 2019 , was as follows: (in thousands, except years and per share data) Number of Options Outstanding Weighted-Average Exercise Price Per Share Weighted-Average Remaining Contractual Term (Years) Aggregate Intrinsic Value Outstanding at January 31, 2 019 13,648 $ 12.27 5.38 $ 507,371 Exercised (5,746 ) 10.09 Canceled/expired (30 ) 17.67 Outstanding at October 31, 2 019 7,872 $ 13.85 5.40 $ 412,060 Vested and expected to vest at October 31, 2019 7,803 $ 13.81 5.40 $ 408,684 Exercisable at October 31, 2019 6,883 $ 13.30 5.10 $ 364,048 As of October 31, 2019 , our total unrecognized compensation cost related to stock option grants was $7.2 million . We expect to recognize this expense over the remaining weighted-average period of approximately 1.2 years. 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 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 performance-based or market-based vesting conditions. 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. As of October 31, 2019 , we had 0.3 million unvested RSUs subject to performance-based conditions for which the performance condition was deemed probable as of period end and 0.2 million unvested RSUs subject to market-based conditions. RSU activity for the nine months ended October 31, 2019 , 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 5,747 54.03 Vested (5,907 ) 28.66 Canceled (1,853 ) 38.66 Unvested at October 31, 2019 15,129 $ 43.76 As of October 31, 2019 , our total unrecognized compensation cost related to RSUs was $482.8 million . We expect to recognize this expense over the remaining weighted-average period of approximately 2.4 years. 2018 Employee Stock Purchase Plan Our 2018 Employee Stock Purchase Plan (“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 on September 15 and March 15 of each year. In the nine months ended October 31, 2019 , 0.5 million shares of our common stock were purchased under the ESPP. Compensation expense related to the ESPP was $2.4 million and $6.4 million for the three and nine months ended October 31, 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 October 31, 2019 , 5.0 million shares were reserved for future issuance under the ESPP.

Net Loss per Share Attributable

Net Loss per Share Attributable to Common Stockholders	9 Months Ended
	Oct. 31, 2019
Earnings Per Share [Abstract]
Net Loss per Share Attributable to Common Stockholders	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: Three Months Ended October 31, Nine Months Ended October 31, (in thousands, except per share data) 2019 2018 2019 2018 Numerator: Net loss $ (46,598 ) $ (52,813 ) $ (160,952 ) $ (360,214 ) Less: preferred stock accretion — — — (353 ) Net loss attributable to common stockholders $ (46,598 ) $ (52,813 ) $ (160,952 ) $ (360,567 ) Denominator: Weighted-average common shares outstanding 178,314 167,736 175,303 124,343 Net loss per share attributable to common stockholders: Basic and diluted $ (0.26 ) $ (0.31 ) $ (0.92 ) $ (2.90 ) Outstanding potentially dilutive securities that were excluded from the diluted per share calculations because they would have been antidilutive are as follows: October 31, (in thousands) 2019 2018 Stock options 7,872 17,629 RSUs 14,600 18,598 ESPP 273 — Total antidilutive securities 22,745 36,227 The table above does not include 0.5 million and 0.7 million RSUs outstanding as of October 31, 2019 and 2018 , as these RSUs are subject to performance-based vesting conditions that were not considered to be met as of the end of the reporting period.

Income Taxes

Income Taxes	9 Months Ended
	Oct. 31, 2019
Income Tax Disclosure [Abstract]
Income Taxes	Income Taxes Our provision for or benefit from income taxes for interim periods is determined using an estimate of our annual effective tax rate, adjusted for discrete items, if any, that are taken into account in the relevant period. Each quarter, we update our estimate of the annual effective tax rate, and if our estimated tax rate changes, we make a cumulative adjustment. Our income tax provision was $1.0 million and income tax benefit was $5.7 million for the three months ended October 31, 2019 and 2018 . Our income tax provision was $3.6 million and income tax benefit was $3.1 million for the nine months ended October 31, 2019 and 2018 . The provision was primarily due to foreign tax expenses, resulting foreign earnings in certain foreign jurisdictions, partially offset by excess benefits from stock option settlements. We review the likelihood that we will realize the benefit of our deferred tax assets and, therefore, the need for valuation allowances, on a quarterly basis. There is no corresponding income tax benefit recognized with respect to losses incurred and no corresponding income tax expense recognized with respect to earnings generated in jurisdictions with a valuation allowance. This causes variability in our effective tax rate. We maintain a valuation allowance against certain deferred tax assets, including all federal, state, and certain foreign deferred tax assets as a result of uncertainties regarding the realization of the asset balance due to historical losses, the variability of operating results, and uncertainty regarding near term projected results. In the event that we determine the deferred tax assets are realizable based on its assessment of relevant factors, an adjustment to the valuation allowance may increase income in the period such determination is made. As of October 31, 2019 , our gross unrecognized tax benefits totaled $11.4 million , excluding related accrued interest and penalties, all of which would impact the effective tax rate if recognized. Our policy is to account for interest and penalties related to uncertain tax positions as a component of income tax provision. We do not expect to have any significant changes to unrecognized tax benefits during the next twelve months. We are subject to taxation in the U.S. and various state and foreign jurisdictions. Earnings from international activities are subject to local country income tax. The material jurisdictions where we are subject to potential examination by taxing authorities include the U.S., California and Israel. We are currently under an income tax examination by the Israel Tax Authority for tax years 2013 through 2016. We are not currently under audit by the Internal Revenue Service or any similar taxing authority in any other material jurisdiction. We believe that adequate amounts have been reserved in all jurisdictions.

Geographic Information

Geographic Information	9 Months Ended
	Oct. 31, 2019
Segment Reporting [Abstract]
Geographic Information	Geographic Information We operate in one operating and one reportable segment as we only report financial information on an aggregate and consolidated basis to the Chief Executive Officer, who is our chief operating decision maker. Revenue by geography is generally based on the address of the customer as specified in our master subscription agreement. Revenue by geographic area was as follows: Three Months Ended October 31, Nine Months Ended October 31, (in thousands) 2019 2018 2019 2018 U.S. $ 206,439 $ 147,677 $ 576,441 $ 416,034 International 43,063 30,708 122,635 85,203 Total revenue $ 249,502 $ 178,385 $ 699,076 $ 501,237 No single country other than the U.S. had revenue greater than 10% of total revenue for the three and nine months ended October 31, 2019 and 2018 . Our long-lived assets by geographic area, which consist of property and equipment, net and operating lease right-of-use assets, net were as follows: (in thousands) October 31, 2019 January 31, 2019 U.S. $ 155,561 $ 60,625 International 86,983 15,207 Total long-lived assets $ 242,544 $ 75,832

Summary of Significant Accoun_2

Summary of Significant Accounting Policies (Policies)	9 Months Ended
	Oct. 31, 2019
Accounting Policies [Abstract]
Principles of Consolidation	Our condensed consolidated financial statements include the accounts of DocuSign, Inc. and our subsidiaries. All intercompany transactions and balances have been eliminated in consolidation.
Basis of Presentation	Our condensed consolidated financial statements have been prepared in accordance with United States (“U.S.”) generally accepted accounting principles (“GAAP”) for interim financial information. Certain information and note disclosures normally included in the financial statements prepared in accordance with GAAP have been condensed or omitted pursuant to the applicable rules and regulations of the Securities and Exchange Commission (“SEC”). Therefore, these unaudited interim consolidated financial statements should be read in conjunction with the consolidated financial statements and related notes included in our 2019 Annual Report on Form 10-K. Our condensed consolidated financial statements are unaudited and have been prepared on a basis consistent with that used to prepare the audited annual consolidated financial statements and, in our opinion, include all adjustments of a normal recurring nature necessary for the fair statement of our financial position, results of operations and cash flows. Our condensed consolidated balance sheet as of January 31, 2019 was derived from audited financial statements but does not include all disclosures required by GAAP. The results of operations for the nine months ended October 31, 2019 are not necessarily indicative of the results to be expected for the year ending January 31, 2020 .
Fiscal Year	Our fiscal year ends on January 31. References to fiscal 2020 , for example, are to the fiscal year ending January 31, 2020 .
Use of Estimates	The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates. Items subject to such estimates and assumptions include those related to the allocation of revenue between recognized and deferred amounts, allowance for bad debts, goodwill, intangible assets, deferred contract acquisition costs, customer benefit period, fair value of financial instruments, valuation of stock-based compensation, valuation of common stock, f air value of the liability and equity components of the convertible notes, whether an arrangement is or contains a lease, the discount rate used for operating leases, and the valuation allowance for deferred income taxes.
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, 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 condensed 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 condensed 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.
Recently Adopted Accounting Pronouncements and Other Recent 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 to the consolidated statements of operations or statements of cash flows. Other Recent Accounting Pronouncements In June 2016, the Financial Accounting Standards Board (“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 ASUs 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 ASUs are effective for interim and annual periods beginning after December 15, 2019. We are evaluating the impact of the adoption of the ASUs on our consolidated financial statements. In August 2018, the FASB issued ASU No. 2018-15, Intangibles—Goodwill and Other—Internal-Use Software (Subtopic 350-40), which aligns the requirements for capitalizing implementation costs incurred in a hosting arrangement that is a service contract with the requirements for capitalizing implementation costs incurred to develop or obtain internal-use software (and hosting arrangements that include an internal use software license). The accounting for the service element of a hosting arrangement that is a service contract is not affected by the amendments in this ASU. The ASU is effective for public business entities for interim and annual periods beginning after December 15, 2019. Early adoption is permitted. We are evaluating the impact of the adoption of the ASU on our consolidated financial statements.

Fair Value Measurements (Tables

Fair Value Measurements (Tables)	9 Months Ended
	Oct. 31, 2019
Fair Value Disclosures [Abstract]
Summary of assets and liabilities measured at fair value on a recurring basis	The following table summarizes our financial assets that are measured at fair value on a recurring basis during the period: October 31, 2019 (in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Level 1: Cash equivalents Money market funds $ 82,438 $ — $ — $ 82,438 Level 2: Available-for-sale securities Commercial paper 31,415 26 — 31,441 Corporate notes and bonds 368,440 982 (67 ) 369,355 U.S. Treasury securities 135,550 313 (3 ) 135,860 U.S. government agency securities 177,083 181 (57 ) 177,207 Level 2 total 712,488 1,502 (127 ) 713,863 Total $ 794,926 $ 1,502 $ (127 ) $ 796,301 January 31, 2019 (in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Level 1: Cash equivalents Money market funds $ 350,063 $ — $ — $ 350,063 Level 2: Cash equivalents Commercial paper 76,828 — (11 ) 76,817 Corporate notes and bonds 2,998 — — 2,998 U.S. government agency securities 6,491 — — 6,491 Available-for-sale securities Commercial paper 86,655 4 (21 ) 86,638 Corporate notes and bonds 287,496 389 (105 ) 287,780 U.S. Treasury securities 4,982 — (1 ) 4,981 U.S. government agency securities 36,021 7 (4 ) 36,024 Level 2 total 501,471 400 (142 ) 501,729 Total $ 851,534 $ 400 $ (142 ) $ 851,792
Fair value of available-for-sale marketable securities by remaining contractual maturities	The fair value of our available-for-sale marketable securities as of October 31, 2019 , by remaining contractual maturities, were as follows (in thousands): Due in one year or less $ 456,080 Due in one to two years 257,783 $ 713,863

Property and Equipment, Net (Ta

Property and Equipment, Net (Tables)	9 Months Ended
	Oct. 31, 2019
Property, Plant and Equipment [Abstract]
Property and equipment	Property and equipment consisted of the following: (in thousands) October 31, 2019 January 31, 2019 Computer and network equipment $ 64,204 $ 55,233 Software, including capitalized software development costs 34,371 27,959 Furniture and office equipment 12,343 9,511 Leasehold improvements 48,916 41,464 159,834 134,167 Less: Accumulated depreciation (77,094 ) (66,479 ) 82,740 67,688 Work in progress 23,177 8,144 $ 105,917 $ 75,832

Acquisition of SpringCM Inc. (T

Acquisition of SpringCM Inc. (Tables)	9 Months Ended
	Oct. 31, 2019
Business Combinations [Abstract]
Schedule of assets acquired and liabilities assumed	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
Schedule of identifiable intangible assets estimated useful lives	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
Schedule of unaudited pro forma results	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: (in thousands, except per share data) Three Months Ended Nine Months Ended Revenue $ 181,490 $ 517,507 Net loss (57,433 ) (384,917 ) Net loss per share attributable to common stockholders, basic and diluted (0.34 ) (3.10 )

Goodwill and Intangible Asset_2

Goodwill and Intangible Assets, Net (Tables)	9 Months Ended
	Oct. 31, 2019
Goodwill and Intangible Assets Disclosure [Abstract]
Schedule of carrying amount of goodwill	The changes in the carrying amount of goodwill for the nine months ended October 31, 2019 , were as follows (in thousands): Balance at January 31, 2019 $ 195,225 Cumulative translation adjustment (201 ) Balance at October 31, 2019 $ 195,024
Schedule of intangible assets	Intangible assets consisted of the following: As of October 31, 2019 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 1.9 $ 31,594 $ (24,138 ) $ 7,456 $ 31,594 $ (20,747 ) $ 10,847 Tradenames / trademarks 0.5 2,419 (2,319 ) 100 2,419 (1,858 ) 561 Customer contracts & related relationships 7.7 65,782 (17,110 ) 48,672 65,782 (11,168 ) 54,614 Certifications 0.8 6,917 (5,884 ) 1,033 6,917 (4,846 ) 2,071 Maintenance contracts & related relationships 0.6 1,498 (1,328 ) 170 1,498 (1,104 ) 394 Backlog—Subscription 0.9 6,400 (3,705 ) 2,695 6,400 (1,304 ) 5,096 6.5 $ 114,610 $ (54,484 ) 60,126 $ 114,610 $ (41,027 ) 73,583 Cumulative translation adjustment 633 620 Total $ 60,759 $ 74,203
Schedule of amortization of finite-lived intangible assets	Amortization of finite-lived intangible assets for the three and nine months ended October 31, 2019 and 2018 , was as follows: Three Months Ended October 31, Nine Months Ended October 31, (in thousands) 2019 2018 2019 2018 Cost of subscription revenue $ 1,348 $ 1,632 $ 4,356 $ 4,303 Sales and marketing 2,957 2,257 9,102 3,787 Total $ 4,305 $ 3,889 $ 13,458 $ 8,090
Schedule of future amortization of finite-lived intangibles	As of October 31, 2019 , future amortization of finite-lived intangibles that will be recorded in cost of revenue and operating expenses is estimated as follows, excluding cumulative translation adjustment: Fiscal Period: (in thousands) 2020, remainder $ 4,260 2021 13,818 2022 8,370 2023 6,023 2024 6,023 Thereafter 21,632 Total $ 60,126

Deferred Contract Acquisition_2

Deferred Contract Acquisition and Fulfillment Costs (Tables)	9 Months Ended
	Oct. 31, 2019
Revenue from Contract with Customer [Abstract]
Deferred contract costs	The following table represents a rollforward of our deferred contract acquisition costs: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 115,985 $ 77,344 Additions to deferred contract acquisition costs 66,416 51,038 Amortization of deferred contract acquisition costs (42,099 ) (28,561 ) Cumulative translation adjustment (1,188 ) — Ending balance $ 139,114 $ 99,821 October 31, (in thousands) 2019 2018 Deferred contract acquisition costs, current $ 2,866 $ 2,730 Deferred contract acquisitions costs, noncurrent 136,248 97,091 Total $ 139,114 $ 99,821 The following table represents our contract fulfillment costs, which include third-party service fees: Nine Months Ended October 31, (in thousands) 2019 2018 Beginning balance $ 3,432 $ 3,316 Additions to deferred contract fulfillment costs 11,384 1,507 Amortization of deferred contract fulfillment costs (7,261 ) (1,328 ) Ending balance $ 7,555 $ 3,495 October 31, (in thousands) 2019 2018 Deferred contract fulfillment costs, current $ 4,052 $ 1,042 Deferred contract fulfillment costs, noncurrent 3,503 2,453 Total $ 7,555 $ 3,495

Convertible Senior Notes (Table

Convertible Senior Notes (Tables)	9 Months Ended
	Oct. 31, 2019
Debt Disclosure [Abstract]
Schedule of convertible debt	The net carrying value of the liability component of the Notes was as follows: (in thousands) October 31, 2019 Principal $ 575,000 Less: unamortized debt discount (107,698 ) Less: unamortized transaction costs (8,724 ) Net carrying amount $ 458,578 The net carrying amount of the equity component of the Notes was as follows: (in thousands) October 31, 2019 Proceeds allocated to the conversion option (debt discount) $ 134,667 Less: transaction costs (3,336 ) Net carrying amount $ 131,331 The interest expense recognized related to the Notes was as follows: (in thousands) Three Months Ended October 31, 2019 Nine Months Ended October 31, 2019 Contractual interest expense $ 719 $ 2,157 Amortization of debt discount 6,147 18,175 Amortization of transaction costs 498 1,472 Total $ 7,364 $ 21,804

Leases (Tables)

Leases (Tables)	9 Months Ended
	Oct. 31, 2019
Leases [Abstract]
Operating lease costs	The following table is a summary of our operating lease costs: (in thousands) Three Months Ended Nine Months Ended Operating lease cost $ 6,762 $ 19,055 Short-term lease cost 60 474 Variable lease cost and other, net (25 ) 162 Total lease cost $ 6,797 $ 19,691
Future lease payments	Future lease payments as of October 31, 2019 , were as follows: Fiscal Period: (in thousands, except years and percentages) 2020, remainder $ 5,872 2021 27,502 2022 28,534 2023 28,978 2024 29,103 Thereafter 80,154 Total undiscounted cash flows $ 200,143 Less: imputed interest (31,038 ) Present value of lease liabilities $ 169,105 Weighted average remaining term (years) 7.9 Weighted average discount rate 4.4 %
Future minimum annual lease payments	The future minimum annual lease payments as of January 31, 2019 , related to the outstanding lease agreements were as follows: Fiscal period: (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

Commitments and Contingencies (

Commitments and Contingencies (Tables)	9 Months Ended
	Oct. 31, 2019
Commitments and Contingencies Disclosure [Abstract]
Schedule of noncancelable contractual obligations	As of October 31, 2019 , our noncancelable contractual obligations with a remaining term of more than one year were as follows: Fiscal period: (in thousands) 2020, remainder $ 4,097 2021 15,238 2022 12,522 2023 898 2024 943 Thereafter 4,555 Total $ 38,253

Stockholders' Equity (Tables)

Stockholders' Equity (Tables)	9 Months Ended
	Oct. 31, 2019
Equity [Abstract]
Schedule of stock option activity	Option activity for the nine months ended October 31, 2019 , was as follows: (in thousands, except years and per share data) Number of Options Outstanding Weighted-Average Exercise Price Per Share Weighted-Average Remaining Contractual Term (Years) Aggregate Intrinsic Value Outstanding at January 31, 2 019 13,648 $ 12.27 5.38 $ 507,371 Exercised (5,746 ) 10.09 Canceled/expired (30 ) 17.67 Outstanding at October 31, 2 019 7,872 $ 13.85 5.40 $ 412,060 Vested and expected to vest at October 31, 2019 7,803 $ 13.81 5.40 $ 408,684 Exercisable at October 31, 2019 6,883 $ 13.30 5.10 $ 364,048
Schedule of RSU activity	RSU activity for the nine months ended October 31, 2019 , 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 5,747 54.03 Vested (5,907 ) 28.66 Canceled (1,853 ) 38.66 Unvested at October 31, 2019 15,129 $ 43.76

Net Loss per Share Attributab_2

Net Loss per Share Attributable to Common Stockholders (Tables)	9 Months Ended
	Oct. 31, 2019
Earnings Per Share [Abstract]
Schedule of calculation of basic and diluted loss per share	The following table presents the calculation of basic and diluted net loss per share attributable to common stockholders for periods presented: Three Months Ended October 31, Nine Months Ended October 31, (in thousands, except per share data) 2019 2018 2019 2018 Numerator: Net loss $ (46,598 ) $ (52,813 ) $ (160,952 ) $ (360,214 ) Less: preferred stock accretion — — — (353 ) Net loss attributable to common stockholders $ (46,598 ) $ (52,813 ) $ (160,952 ) $ (360,567 ) Denominator: Weighted-average common shares outstanding 178,314 167,736 175,303 124,343 Net loss per share attributable to common stockholders: Basic and diluted $ (0.26 ) $ (0.31 ) $ (0.92 ) $ (2.90 )
Schedule of antidilutive securities	Outstanding potentially dilutive securities that were excluded from the diluted per share calculations because they would have been antidilutive are as follows: October 31, (in thousands) 2019 2018 Stock options 7,872 17,629 RSUs 14,600 18,598 ESPP 273 — Total antidilutive securities 22,745 36,227

Geographic Information (Tables)

Geographic Information (Tables)	9 Months Ended
	Oct. 31, 2019
Segment Reporting [Abstract]
Revenues by geographic area	Revenue by geographic area was as follows: Three Months Ended October 31, Nine Months Ended October 31, (in thousands) 2019 2018 2019 2018 U.S. $ 206,439 $ 147,677 $ 576,441 $ 416,034 International 43,063 30,708 122,635 85,203 Total revenue $ 249,502 $ 178,385 $ 699,076 $ 501,237
Property and equipment by geographic area	Our long-lived assets by geographic area, which consist of property and equipment, net and operating lease right-of-use assets, net were as follows: (in thousands) October 31, 2019 January 31, 2019 U.S. $ 155,561 $ 60,625 International 86,983 15,207 Total long-lived assets $ 242,544 $ 75,832

Summary of Significant Accoun_3

Summary of Significant Accounting Policies - Narrative (Details) - USD ($)	Oct. 31, 2019	Mar. 31, 2019	Feb. 01, 2019	Jan. 31, 2019
Accounting Policies [Abstract]
Equity investments in privately-held companies		$ 15,500,000		$ 0
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Operating lease right-of-use assets	$ 136,627,000
Operating lease liabilities	169,105,000
Derecognition related to build-to-suit asset	(105,917,000)			$ (75,832,000)
Accounting Standards Update 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Operating lease right-of-use assets			$ 93,900,000
Operating lease liabilities			121,800,000
Deferred rent			26,600,000
Israel Leased Property | Other Capitalized Property Plant and Equipment | Accounting Standards Update 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Derecognition related to build-to-suit asset	$ 2,500,000
Derecognition related to build-to-suit liability			$ 2,500,000

Revenue and Performance Oblig_2

Revenue and Performance Obligations - Additional Information (Details) - USD ($) $ in Millions	3 Months Ended	9 Months Ended
	Oct. 31, 2019	Oct. 31, 2019	Oct. 31, 2018
Disaggregation of Revenue [Line Items]
Remaining performance obligations	$ 673.3	$ 673.3
Subscription | Minimum
Disaggregation of Revenue [Line Items]
Contract term		1 year
Subscription | Maximum
Disaggregation of Revenue [Line Items]
Contract term		3 years
Product concentration risk | Revenue | Subscription
Disaggregation of Revenue [Line Items]
Concentration risk percentage	95.00%	94.00%	95.00%

Fair Value Measurements - Asset

Fair Value Measurements - Assets and Liabilities Measured at Fair Value on a Recurring Basis (Details) - USD ($) $ in Thousands	Oct. 31, 2019	Jan. 31, 2019
Cash equivalents
Amortized Cost	$ 197,697	$ 517,811
Available-for-sale securities
Gross Unrealized Gains	1,502	400
Estimated Fair Value	713,863
Total
Amortized Cost	794,926	851,534
Gross Unrealized Losses	(127)	(142)
Estimated Fair Value	796,301	851,792
Level 2
Available-for-sale securities
Amortized Cost	712,488	501,471
Gross Unrealized Gains	1,502	400
Gross Unrealized Losses	(127)	(142)
Estimated Fair Value	713,863	501,729
Commercial paper | Level 2
Available-for-sale securities
Amortized Cost	31,415	86,655
Gross Unrealized Gains	26	4
Gross Unrealized Losses	0	(21)
Estimated Fair Value	31,441	86,638
Corporate notes and bonds | Level 2
Available-for-sale securities
Amortized Cost	368,440	287,496
Gross Unrealized Gains	982	389
Gross Unrealized Losses	(67)	(105)
Estimated Fair Value	369,355	287,780
U.S. Treasury securities | Level 2
Available-for-sale securities
Amortized Cost	135,550	4,982
Gross Unrealized Gains	313	0
Gross Unrealized Losses	(3)	(1)
Estimated Fair Value	135,860	4,981
U.S. government agency securities | Level 2
Available-for-sale securities
Amortized Cost	177,083	36,021
Gross Unrealized Gains	181	7
Gross Unrealized Losses	(57)	(4)
Estimated Fair Value	177,207	36,024
Money market funds | Level 1
Cash equivalents
Amortized Cost	82,438	350,063
Estimated Fair Value	$ 82,438	350,063
Commercial paper | Level 2
Cash equivalents
Amortized Cost		76,828
Gross Unrealized Losses		(11)
Estimated Fair Value		76,817
Corporate notes and bonds | Level 2
Cash equivalents
Amortized Cost		2,998
Estimated Fair Value		2,998
U.S. government agency securities | Level 2
Cash equivalents
Amortized Cost		6,491
Estimated Fair Value		$ 6,491

Revenue and Performance Oblig_3

Revenue and Performance Obligations - Remaining Performance Obligations (Details)	Oct. 31, 2019
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction, Start Date [Axis]: 2019-05-01
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction [Line Items]
Remaining performance obligations, period of recognition	1 year
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction, Start Date [Axis]: 2019-11-01
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction [Line Items]
Remaining performance obligation, percentage	54.00%

Fair Value Measurements - Fair

Fair Value Measurements - Fair Value of Available-for-Sale Marketable Securities by Remaining Contractual Maturities (Details) $ in Thousands	Oct. 31, 2019USD ($)
Fair Value Disclosures [Abstract]
Due in one year or less	$ 456,080
Due in one to two years	257,783
Total available-for-sale securities	$ 713,863

Fair Value Measurements - Narra

Fair Value Measurements - Narrative (Details)	Oct. 31, 2019USD ($)security	Sep. 30, 2018USD ($)
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Number of available-for-sale securities | security	181
Level 2
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Fair value of debt	$ 673,500,000
Convertible Debt | Convertible Senior Notes Due 2023
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Debt interest rate percentage	0.50%
Aggregate principal amount of debt issued	$ 575,000,000	$ 575,000,000

Property and Equipment, Net (De

Property and Equipment, Net (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018	Oct. 31, 2019	Oct. 31, 2018	Jan. 31, 2019
Property, Plant and Equipment [Line Items]
Property and equipment, net	$ 105,917		$ 105,917		$ 75,832
Depreciation expense	8,400	$ 6,500	23,500	$ 17,900
Computer and network equipment
Property, Plant and Equipment [Line Items]
Property, plant and equipment, gross	64,204		64,204		55,233
Software, including capitalized software development costs
Property, Plant and Equipment [Line Items]
Property, plant and equipment, gross	34,371		34,371		27,959
Furniture and office equipment
Property, Plant and Equipment [Line Items]
Property, plant and equipment, gross	12,343		12,343		9,511
Leasehold improvements
Property, Plant and Equipment [Line Items]
Property, plant and equipment, gross	48,916		48,916		41,464
Property and equipment, excluding work in progress
Property, Plant and Equipment [Line Items]
Property, plant and equipment, gross	159,834		159,834		134,167
Less: Accumulated depreciation	(77,094)		(77,094)		(66,479)
Property and equipment, net	82,740		82,740		67,688
Work in progress
Property, Plant and Equipment [Line Items]
Property and equipment, net	$ 23,177		$ 23,177		8,144
Israel Leased Property | Leasehold improvements
Property, Plant and Equipment [Line Items]
Property and equipment, net					$ 2,500

Acquisition of SpringCM Inc. -

Acquisition of SpringCM Inc. - Narrative (Details) - USD ($) $ in Thousands, shares in Millions	Sep. 04, 2018	Oct. 31, 2019	Oct. 31, 2018	Jan. 31, 2019
Business Acquisition [Line Items]
Cash paid to acquire SpringCM, excluding cash acquired		$ 0	$ 218,779
SpringCM Inc.
Business Acquisition [Line Items]
Cash paid to acquire SpringCM, excluding cash acquired	$ 218,800
Portion of cash paid held in escrow	$ 8,200
Period of time held in escrow	18 months
Acquisition costs				$ 1,800
RSUs with vesting conditions | SpringCM Inc.
Business Acquisition [Line Items]
Shares granted to employees (in shares)		0.5
Unrecognized compensation cost, RSUs		$ 26,500

Acquisition of SpringCM Inc. _2

Acquisition of SpringCM Inc. - Assets Acquired and Liabilities Assumed (Details) - USD ($) $ in Thousands	Oct. 31, 2019	Jan. 31, 2019	Sep. 04, 2018
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Net [Abstract]
Goodwill	$ 195,024	$ 195,225
SpringCM Inc.
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Net [Abstract]
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)
Total assets acquired and liabilities assumed			$ 225,729

Acquisition of SpringCM Inc. _3

Acquisition of SpringCM Inc. - Intangible Assets Acquired (Details) - SpringCM Inc. $ in Thousands	Sep. 04, 2018USD ($)
Acquired Finite-Lived Intangible Assets [Line Items]
Estimated Fair Value	$ 73,000
Existing technology
Acquired Finite-Lived Intangible Assets [Line Items]
Estimated Fair Value	$ 11,900
Expected Useful Life	3 years
Customer relationships—subscription
Acquired Finite-Lived Intangible Assets [Line Items]
Estimated Fair Value	$ 54,200
Expected Useful Life	9 years
Backlog—subscription
Acquired Finite-Lived Intangible Assets [Line Items]
Estimated Fair Value	$ 6,400
Expected Useful Life	2 years
Tradenames / trademarks
Acquired Finite-Lived Intangible Assets [Line Items]
Estimated Fair Value	$ 500
Expected Useful Life	1 year

Acquisition of SpringCM Inc. _4

Acquisition of SpringCM Inc. - Pro Forma Results (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended	9 Months Ended
	Oct. 31, 2018	Oct. 31, 2018
Business Acquisition, Pro Forma Information [Abstract]
Revenue	$ 181,490	$ 517,507
Net loss	$ (57,433)	$ (384,917)
Net loss per share attributable to common stockholders, basic and diluted (in usd per share)	$ (0.34)	$ (3.10)

Goodwill and Intangible Asset_3

Goodwill and Intangible Assets, Net - Goodwill (Details) $ in Thousands	9 Months Ended
	Oct. 31, 2019USD ($)
Goodwill [Roll Forward]
Balance at January 31, 2019	$ 195,225
Cumulative translation adjustment	(201)
Balance at October 31, 2019	$ 195,024

Goodwill and Intangible Asset_4

Goodwill and Intangible Assets, Net - Intangible Assets (Details) - USD ($) $ in Thousands	9 Months Ended
	Oct. 31, 2019	Jan. 31, 2019
Finite-Lived Intangible Assets, Net [Abstract]
Weighted-average Remaining Useful Life (Years)	6 years 6 months
Estimated Fair Value	$ 114,610	$ 114,610
Accumulated Amortization	(54,484)	(41,027)
Acquisition-related intangibles, net, excluding cumulative translation adjustment	60,126	73,583
Cumulative translation adjustment	633	620
Acquisition-related Intangibles, Net	$ 60,759	74,203
Existing technology
Finite-Lived Intangible Assets, Net [Abstract]
Weighted-average Remaining Useful Life (Years)	1 year 10 months 24 days
Estimated Fair Value	$ 31,594	31,594
Accumulated Amortization	(24,138)	(20,747)
Acquisition-related intangibles, net, excluding cumulative translation adjustment	$ 7,456	10,847
Tradenames / trademarks
Finite-Lived Intangible Assets, Net [Abstract]
Weighted-average Remaining Useful Life (Years)	15 days
Estimated Fair Value	$ 2,419	2,419
Accumulated Amortization	(2,319)	(1,858)
Acquisition-related intangibles, net, excluding cumulative translation adjustment	$ 100	561
Customer contracts & related relationships
Finite-Lived Intangible Assets, Net [Abstract]
Weighted-average Remaining Useful Life (Years)	7 years 8 months 12 days
Estimated Fair Value	$ 65,782	65,782
Accumulated Amortization	(17,110)	(11,168)
Acquisition-related intangibles, net, excluding cumulative translation adjustment	$ 48,672	54,614
Certifications
Finite-Lived Intangible Assets, Net [Abstract]
Weighted-average Remaining Useful Life (Years)	24 days
Estimated Fair Value	$ 6,917	6,917
Accumulated Amortization	(5,884)	(4,846)
Acquisition-related intangibles, net, excluding cumulative translation adjustment	$ 1,033	2,071
Maintenance contracts & related relationships
Finite-Lived Intangible Assets, Net [Abstract]
Weighted-average Remaining Useful Life (Years)	18 days
Estimated Fair Value	$ 1,498	1,498
Accumulated Amortization	(1,328)	(1,104)
Acquisition-related intangibles, net, excluding cumulative translation adjustment	$ 170	394
Backlog—Subscription
Finite-Lived Intangible Assets, Net [Abstract]
Weighted-average Remaining Useful Life (Years)	27 days
Estimated Fair Value	$ 6,400	6,400
Accumulated Amortization	(3,705)	(1,304)
Acquisition-related intangibles, net, excluding cumulative translation adjustment	$ 2,695	$ 5,096

Goodwill and Intangible Asset_5

Goodwill and Intangible Assets, Net - Amortization (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018	Oct. 31, 2019	Oct. 31, 2018
Finite-Lived Intangible Assets [Line Items]
Amortization of finite-lived intangible assets	$ 4,305	$ 3,889	$ 13,458	$ 8,090
Cost of subscription revenue
Finite-Lived Intangible Assets [Line Items]
Amortization of finite-lived intangible assets	1,348	1,632	4,356	4,303
Sales and marketing
Finite-Lived Intangible Assets [Line Items]
Amortization of finite-lived intangible assets	$ 2,957	$ 2,257	$ 9,102	$ 3,787

Goodwill and Intangible Asset_6

Goodwill and Intangible Assets, Net - Future Amortization (Details) - USD ($) $ in Thousands	Oct. 31, 2019	Jan. 31, 2019
Finite-Lived Intangible Assets, Amortization Expense, Maturity Schedule [Abstract]
2020, remainder	$ 4,260
2021	13,818
2022	8,370
2023	6,023
2024	6,023
Thereafter	21,632
Acquisition-related intangibles, net, excluding cumulative translation adjustment	$ 60,126	$ 73,583

Contract Balances (Details)

Contract Balances (Details) - USD ($) $ in Millions	9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018	Jan. 31, 2019
Revenue from Contract with Customer [Abstract]
Contract assets	$ 19.2		$ 11.9
Contract assets, noncurrent	1.2		$ 1.3
Revenue recognized that was included in contract liability balance at the beginning of the period	$ 342.6	$ 238.1
Payment term	30 days

Deferred Contract Acquisition_3

Deferred Contract Acquisition and Fulfillment Costs (Details) - USD ($) $ in Thousands	9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018	Oct. 31, 2019	Jan. 31, 2019	Oct. 31, 2018	Jul. 31, 2018
Capitalized Contract Cost, Net [Roll Forward]
Amortization of deferred contract acquisition costs	$ (49,360)	$ (29,889)
Deferred contract acquisitions costs, noncurrent			$ 136,248	$ 112,583
Contract acquisition costs
Capitalized Contract Cost, Net [Roll Forward]
Beginning balance	115,985	77,344
Additions to deferred contract acquisition costs	66,416	51,038
Amortization of deferred contract acquisition costs	(42,099)	(28,561)
Cumulative translation adjustment	(1,188)	0
Ending balance	139,114	99,821
Deferred contract acquisition costs, current			2,866			$ 2,730
Deferred contract acquisitions costs, noncurrent			136,248			97,091
Total	115,985	77,344	139,114	115,985	$ 99,821	$ 99,821
Contract fulfillment costs
Capitalized Contract Cost, Net [Roll Forward]
Beginning balance	3,432	3,316
Additions to deferred contract acquisition costs	11,384	1,507
Amortization of deferred contract acquisition costs	(7,261)	(1,328)
Ending balance	7,555	3,495
Deferred contract acquisition costs, current			4,052		1,042
Deferred contract acquisitions costs, noncurrent			3,503		2,453
Total	$ 3,432	$ 3,316	$ 7,555	$ 3,432	$ 3,495

Convertible Senior Notes - Narr

Convertible Senior Notes - Narrative (Details) $ / shares in Units, shares in Millions	1 Months Ended	3 Months Ended	9 Months Ended
	Sep. 30, 2018USD ($)trading_day$ / sharesshares	Oct. 31, 2018USD ($)	Oct. 31, 2019USD ($)	Oct. 31, 2018USD ($)
Debt Conversion [Line Items]
Proceeds from issuance of debt			$ 0	$ 560,756,000
Costs incurred for capped calls		$ 67,563,000		$ 67,563,000
Convertible Senior Notes Due 2023 | Convertible Debt
Debt Conversion [Line Items]
Aggregate principal amount of debt issued	$ 575,000,000		575,000,000
Additional principal amount purchased	75,000,000
Proceeds from issuance of debt	$ 560,800,000
Conversion rate	0.013986
Conversion price (in usd per share) | $ / shares	$ 71.50
Percentage of principal amount redeemed	100.00%
Trading days | trading_day	20
Consecutive trading days | trading_day	30
Percentage of conversion price	130.00%
Equity component of conversion option			134,667,000
Transaction costs attributable to liability component			10,900,000
Transaction costs attributable to equity components			$ 3,336,000
Capped Calls
Debt Conversion [Line Items]
Conversion price (in usd per share) | $ / shares	$ 71.50
Initial cap price (in usd per share) | $ / shares	$ 110
Shares covered by capped calls (in shares) | shares	8
Costs incurred for capped calls	$ 67,600,000
Conversion Covenant One | Convertible Senior Notes Due 2023 | Convertible Debt
Debt Conversion [Line Items]
Trading days | trading_day	20
Consecutive trading days | trading_day	30
Percentage of conversion price	130.00%
Conversion Covenant Two | Convertible Senior Notes Due 2023 | Convertible Debt
Debt Conversion [Line Items]
Trading days | trading_day	5
Consecutive trading days | trading_day	10
Percentage of conversion price	98.00%
Measurement Input, Discount Rate | Convertible Senior Notes Due 2023 | Convertible Debt
Debt Conversion [Line Items]
Discount rate			0.06

Convertible Senior Notes - Carr

Convertible Senior Notes - Carrying Value of Liability Component (Details) - Convertible Senior Notes Due 2023 - Convertible Debt $ in Thousands	Oct. 31, 2019USD ($)
Debt Instrument [Line Items]
Principal	$ 575,000
Less: unamortized debt discount	(107,698)
Less: unamortized transaction costs	(8,724)
Net carrying amount	$ 458,578

Convertible Senior Notes - Ca_2

Convertible Senior Notes - Carrying Amount of Equity Component (Details) - Convertible Debt - Convertible Senior Notes Due 2023 $ in Thousands	Oct. 31, 2019USD ($)
Debt Instrument [Line Items]
Proceeds allocated to the conversion option (debt discount)	$ 134,667
Less: transaction costs	(3,336)
Net carrying amount	$ 131,331

Convertible Senior Notes - Inte

Convertible Senior Notes - Interest Expense (Details) - Convertible Debt - Convertible Senior Notes Due 2023 - USD ($) $ in Thousands	3 Months Ended	9 Months Ended
	Oct. 31, 2019	Oct. 31, 2019
Debt Instrument [Line Items]
Contractual interest expense	$ 719	$ 2,157
Amortization of debt discount	6,147	18,175
Amortization of transaction costs	498	1,472
Total	$ 7,364	$ 21,804

Leases - Narrative (Details)

Leases - Narrative (Details) $ in Millions	Jul. 31, 2019contract	Oct. 31, 2019USD ($)
Leases [Abstract]
Number of lease contracts | contract	0
Operating lease commitments not yet commenced | $		$ 26.2
Terms of lease		8 years

Leases - Operating Lease Costs

Leases - Operating Lease Costs (Details) - USD ($) $ in Thousands	3 Months Ended	9 Months Ended
	Oct. 31, 2019	Oct. 31, 2019
Leases [Abstract]
Operating lease cost	$ 6,762	$ 19,055
Short-term lease cost	60	474
Variable lease cost and other, net	(25)	162
Total lease cost	$ 6,797	$ 19,691

Leases - Future Lease Payments

Leases - Future Lease Payments (Details) - USD ($) $ in Thousands	Oct. 31, 2019	Jan. 31, 2019
Future lease payments due:
2020, remainder	$ 5,872
2021	27,502
2022	28,534
2023	28,978
2024	29,103
Thereafter	80,154
Total undiscounted cash flows	200,143
Less: imputed interest	(31,038)
Present value of lease liabilities	$ 169,105
Weighted average remaining term (years)	7 years 10 months 24 days
Weighted average discount rate	4.40%
Future minimum annual lease payments:
2020		$ 22,198
2021		22,617
2022		22,556
2023		23,173
2024		23,373
Thereafter		34,634
Total minimum lease payments		$ 148,551

Commitments and Contingencies -

Commitments and Contingencies - Narrative (Details) $ in Millions	Oct. 31, 2019USD ($)
Commitments and Contingencies Disclosure [Abstract]
Letters of credit outstanding	$ 9.9

Commitments and Contingencies_2

Commitments and Contingencies - Future Purchase Obligations (Details) $ in Thousands	Oct. 31, 2019USD ($)
Purchase Obligation, Fiscal Year Maturity [Abstract]
2020, remainder	$ 4,097
2021	15,238
2022	12,522
2023	898
2024	943
Thereafter	4,555
Total	$ 38,253

Stockholders' Equity - Narrativ

Stockholders' Equity - Narrative (Details) shares in Thousands, $ in Thousands	Apr. 26, 2018USD ($)	Oct. 31, 2019USD ($)planshares	Oct. 31, 2019USD ($)planshares	Oct. 31, 2018USD ($)	Jan. 31, 2019shares	Feb. 01, 2019shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of stock-based compensation plans | plan		3	3
Unrecognized compensation cost, options | $		$ 7,200	$ 7,200
Employee stock purchase plan, compensation expense | $			$ 150,799	$ 361,707
Stock options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, remaining weighted-average period for recognition			1 year 2 months 12 days
RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Vesting percentage			25.00%
Unrecognized compensation cost, remaining weighted-average period for recognition			2 years 4 months 24 days
Service period			4 years
Accelerated share based compensation expense | $	$ 262,800
Unvested subject to performance based conditions (in shares)		15,129	15,129		17,142
Shares granted (in shares)			5,747
Unrecognized compensation cost, RSUs | $		$ 482,800	$ 482,800
Performance-based Restricted Stock Units
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unvested subject to performance based conditions (in shares)		300	300
Restricted Stock Units with Market-based Conditions
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unvested subject to performance based conditions (in shares)		200	200
ESPP
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Employee stock purchase plan, shares purchased (in shares)			500
Employee stock purchase plan, compensation expense | $		$ 2,400	$ 6,400
2018 Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Reserved for future issuance (in shares)		24,500	24,500
Annual increase in shares reserved, percentage of total shares			5.00%
Number of shares reserved for future issuance						8,500
2018 ESPP
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Reserved for future issuance (in shares)		5,000	5,000		3,800
Annual increase in shares reserved, percentage of total shares					1.00%
Employee contribution, maximum percentage of earnings					15.00%
Employee stock purchase plan, purchase price of common stock, percent of market price					85.00%
Employee stock purchase plan offering period			6 months

Stockholders' Equity - Stock Op

Stockholders' Equity - Stock Option Activity (Details) $ / shares in Units, shares in Thousands, $ in Thousands	9 Months Ended	12 Months Ended
	Oct. 31, 2019USD ($)$ / sharesshares	Jan. 31, 2019USD ($)$ / sharesshares
Number of Options Outstanding
Beginning balance (in shares) | shares	13,648
Options exercised (in shares) | shares	(5,746)
Options canceled/expired (in shares) | shares	(30)
Ending balance (in shares) | shares	7,872	13,648
Vested and expected to vest (in shares) | shares	7,803
Exercisable (in shares) | shares	6,883
Weighted-Average Exercise Price Per Share
Beginning balance (in usd per share) | $ / shares	$ 12.27
Options exercised (in usd per share) | $ / shares	10.09
Options canceled/expired (in usd per share) | $ / shares	17.67
Ending balance (in usd per share) | $ / shares	13.85	$ 12.27
Vested and expected to vest (in usd per share) | $ / shares	13.81
Exercisable (in usd per share) | $ / shares	$ 13.30
Weighted-Average Remaining Contractual Term
Balance	5 years 4 months 24 days	5 years 4 months 17 days
Vested and expected to vest	5 years 4 months 24 days
Exercisable	5 years 1 month 6 days
Aggregate Intrinsic Value
Balance | $	$ 412,060	$ 507,371
Vested and expected to vest | $	408,684
Exercisable | $	$ 364,048

Stockholders' Equity - RSU Acti

Stockholders' Equity - RSU Activity (Details) - RSUs shares in Thousands	9 Months Ended
	Oct. 31, 2019$ / sharesshares
Number of Units
Unvested at beginning of period (in shares) | shares	17,142
Granted (in shares) | shares	5,747
Vested (in shares) | shares	(5,907)
Canceled (in shares) | shares	(1,853)
Unvested at end of period (in shares) | shares	15,129
Weighted-Average Grant Date Fair Value
Unvested at beginning of period (in usd per share) | $ / shares	$ 34.56
Granted (in usd per share) | $ / shares	54.03
Vested (in usd per share) | $ / shares	28.66
Canceled (in usd per share) | $ / shares	38.66
Unvested at end of period (in usd per share) | $ / shares	$ 43.76

Net Loss per Share Attributab_3

Net Loss per Share Attributable to Common Stockholders - Calculation of basic and diluted net loss per share (Details) - USD ($) $ / shares in Units, shares in Thousands, $ in Thousands	3 Months Ended		9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018	Oct. 31, 2019	Oct. 31, 2018
Numerator:
Net loss	$ (46,598)	$ (52,813)	$ (160,952)	$ (360,214)
Less: preferred stock accretion	0	0	0	(353)
Net loss attributable to common stockholders	$ (46,598)	$ (52,813)	$ (160,952)	$ (360,567)
Denominator:
Weighted-average common shares outstanding (in shares)	178,314	167,736	175,303	124,343
Net loss per share attributable to common stockholders:
Basic and diluted (in usd per share)	$ (0.26)	$ (0.31)	$ (0.92)	$ (2.90)

Net Loss per Share Attributab_4

Net Loss per Share Attributable to Common Stockholders - Antidilutive Securities (Details) - shares shares in Thousands	9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	22,745	36,227
Stock options
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	7,872	17,629
RSUs
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	14,600	18,598
ESPP
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	273	0

Net Loss per Share Attributab_5

Net Loss per Share Attributable to Common Stockholders - Narrative (Details) - shares shares in Millions	Oct. 31, 2019	Oct. 31, 2018
RSUs with vesting conditions
IPO, Sale of Stock [Line Items]
RSUs outstanding (in shares)	0.5	0.7

Income Taxes (Details)

Income Taxes (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Oct. 31, 2019	Oct. 31, 2018	Oct. 31, 2019	Oct. 31, 2018
Income Tax Disclosure [Abstract]
Provision for (benefit from) income taxes	$ 1,038	$ (5,712)	$ 3,552	$ (3,059)
Uncertain tax benefits	$ 11,400		$ 11,400

Geographic Information (Details

Geographic Information (Details) $ in Thousands	3 Months Ended		9 Months Ended
	Oct. 31, 2019USD ($)	Oct. 31, 2018USD ($)	Oct. 31, 2019USD ($)segment	Oct. 31, 2018USD ($)	Jan. 31, 2019USD ($)
Revenues from External Customers and Long-Lived Assets [Line Items]
Number of operating segments | segment			1
Number of reportable segments | segment			1
Total revenue	$ 249,502	$ 178,385	$ 699,076	$ 501,237
Total long-lived assets	242,544		242,544		$ 75,832
U.S.
Revenues from External Customers and Long-Lived Assets [Line Items]
Total revenue	206,439	147,677	576,441	416,034
Total long-lived assets	155,561		155,561		60,625
International
Revenues from External Customers and Long-Lived Assets [Line Items]
Total revenue	43,063	$ 30,708	122,635	$ 85,203
Total long-lived assets	$ 86,983		$ 86,983		$ 15,207

Uncategorized Items - q32010q.h

Label	Element	Value
Accounting Standards Update 2016-02 [Member]
Cumulative Effect of New Accounting Principle in Period of Adoption	us-gaap_CumulativeEffectOfNewAccountingPrincipleInPeriodOfAdoption	$ (48,000)
Accounting Standards Update 2016-02 [Member] | Retained Earnings [Member]
Cumulative Effect of New Accounting Principle in Period of Adoption	us-gaap_CumulativeEffectOfNewAccountingPrincipleInPeriodOfAdoption	$ (48,000)