DOCUSIGN, INC. 10-K

ITEM 7A. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK We are exposed to market risks in the ordinary course of our business. Market risk represents the risk of loss that may impact our financial position due to adverse changes in financial market prices and rates. Our market risk exposure is primarily the result of fluctuations in foreign currency exchange and interest rates. Interest Rate Risk As of January 31, 2022, we had cash, cash equivalents and investments totaling $897.8 million, which consisted primarily of bank deposits, money market funds, commercial paper, corporate notes and bonds and U.S. Treasury and government agency securities. Interest-earning instruments carry a degree of interest rate risk. Our investment portfolio is composed of highly rated securities and limits the amount of credit exposure to any one issuer. A hypothetical 100 basis point increase in interest rates would result in an approximate $2.5 million decrease of the fair value of our investment portfolio as of January 31, 2022. Such losses would only be realized if we sold the investments prior to maturity. We do not enter into investments for trading or speculative purposes and have not used any derivative financial instruments to manage our interest rate risk exposure. We had no exposure to changes in interest rates from debt obligations at January 31, 2022 as our 2023 Notes and 2024 Notes were issued at fixed rates of 0.5% and 0.0%, respectively. The fair value of the Notes changes when the market price of our stock fluctuates or interest rates change. However, we carry the Notes at face value less unamortized discount on our balance sheet and present the fair value for required disclosure purposes only. Foreign Currency Exchange Risk Our reporting currency is the U.S. dollar, and the functional currency of each of our subsidiaries is either its local currency or the U.S. dollar, depending on the circumstances. The assets and liabilities of each of our subsidiaries are translated into U.S. dollars at exchange rates in effect at each balance sheet date. Operations accounts are translated using the average exchange rate for the relevant period. A strengthening or weakening of the U.S. dollar against the other currencies may negatively or positively affect our operating results as expressed in U.S. dollars. Foreign currency translation adjustments are accounted for as a component of “Accumulated other comprehensive income (loss)” within “Stockholders’ equity”. Gains or losses due to remeasurements of transactions denominated in foreign currencies are included in “Interest income and other income, net” in our consolidated statements of operations and comprehensive loss. We have not engaged in the hedging of foreign currency transactions to date, although we may choose to do so in the future. We do not believe that an immediate 10% increase or decrease in the relative value of the U.S. dollar to other currencies would have a material effect on our operating results. DocuSign, Inc.| 2022 Form 10-K | 59 ITEM 8. CONSOLIDATED FINANCIAL STATEMENTS Index Report of Independent Registered Public Accounting Firm (PC AO B ID 238 ) 61 Consolidated Financial Statements 63 Consolidated Balance Sheets as of January 31, 2022 and 2021 63 Consolidated Statements of Operations and Comprehensive Loss for the Years Ended January 31, 2022 , 2021 and 2020 64 Consolidated Statements of Stockholders’ Equity for the Years Ended January 31, 2022 , 2021 and 2020 65 Consolidated Statements of Cash Flows for the Years Ended January 31, 2022 , 2021 and 2020 67 Notes to Consolidated Financial Statements 69 Note 1 Summary of Significant Accounting Policies 69 Note 2 Revenue and Performance Obligations 78 Note 3 Fair Value Measurements 79 Note 4 Property and Equipment, Net 81 Note 5 Acquisitions 81 Note 6 Goodwill and Intangible Assets, Net 83 Note 7 Deferred Contract Acquisition and Fulfillment Costs 85 Note 8 Debt 85 Note 9 Leases 89 Note 10 Commitments and Contingencies 90 Note 11 Stockholders' Equity 91 Note 12 Net Loss Per Share Attributable to Common Stockholders 94 Note 13 Employee Benefit Plan 94 Note 14 Income Taxes 94 Note 15 Geographic Information 98 Note 16 Subsequent Events 98 DocuSign, Inc.| 2022 Form 10-K | 60 Report of Independent Registered Public Accounting Firm To the Board of Directors and Stockholders of DocuSign, Inc. Opinions on the Financial Statements and Internal Control over Financial Reporting We have audited the accompanying consolidated balance sheets of DocuSign, Inc. and its subsidiaries (the “Company”) as of January 31, 2022 and 2021, and the related consolidated statements of operations and comprehensive loss, of stockholders’ equity and of cash flows for each of the three years in the period ended January 31, 2022, including the related notes (collectively referred to as the “consolidated financial statements”). We also have audited the Company's internal control over financial reporting as of January 31, 2022, based on criteria established in Internal Control - Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (COSO). In our opinion, the consolidated financial statements referred to above present fairly, in all material respects, the financial position of the Company as of January 31, 2022 and 2021, and the results of its operations and its cash flows for each of the three years in the period ended January 31, 2022 in conformity with accounting principles generally accepted in the United States of America. Also in our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of January 31, 2022, based on criteria established in Internal Control - Integrated Framework (2013) issued by the COSO. Changes in Accounting Principles As discussed in Note 1 to the consolidated financial statements, the Company changed the manner in which it accounts for convertible debt effective February 1, 2021 and the manner in which it accounts for leases effective February 1, 2019. Basis for Opinions The Company's management is responsible for these consolidated financial statements, for maintaining effective internal control over financial reporting, and for its assessment of the effectiveness of internal control over financial reporting, included in Management’s Annual Report on Internal Control over Financial Reporting appearing under Item 9A. Our responsibility is to express opinions on the Company’s consolidated financial statements and on the Company's internal control over financial reporting based on our audits. We are a public accounting firm registered with the Public Company Accounting Oversight Board (United States) (PCAOB) and are required to be independent with respect to the Company in accordance with the U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB. We conducted our audits in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audits to obtain reasonable assurance about whether the consolidated financial statements are free of material misstatement, whether due to error or fraud, and whether effective internal control over financial reporting was maintained in all material respects. Our audits of the consolidated financial statements included performing procedures to assess the risks of material misstatement of the consolidated financial statements, whether due to error or fraud, and performing procedures that respond to those risks. Such procedures included examining, on a test basis, evidence regarding the amounts and disclosures in the consolidated financial statements. Our audits also included evaluating the accounting principles used and significant estimates made by management, as well as evaluating the overall presentation of the consolidated financial statements. Our audit of internal control over financial reporting included obtaining an understanding of internal control over financial reporting, assessing the risk that a material weakness exists, and testing and evaluating the design and operating effectiveness of internal control based on the assessed risk. Our audits also included performing such other procedures as we considered necessary in the circumstances. We believe that our audits provide a reasonable basis for our opinions. Definition and Limitations of Internal Control over Financial Reporting A company’s internal control over financial reporting is a process designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles. A company’s internal control over financial reporting includes those policies and procedures that (i) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the transactions and dispositions of the assets of the company; (ii) provide reasonable assurance that transactions are recorded as necessary to permit preparation of financial statements in accordance with generally accepted accounting principles, and that receipts and expenditures of the company are being made only in accordance with authorizations of management and directors of the company; and (iii) provide reasonable assurance regarding prevention or timely DocuSign, Inc.| 2022 Form 10-K | 61 detection of unauthorized acquisition, use, or disposition of the company’s assets that could have a material effect on the financial statements. Because of its inherent limitations, internal control over financial reporting may not prevent or detect misstatements. Also, projections of any evaluation of effectiveness to future periods are subject to the risk that controls may become inadequate because of changes in conditions, or that the degree of compliance with the policies or procedures may deteriorate. Critical Audit Matters The critical audit matter communicated below is a matter arising from the current period audit of the consolidated financial statements that was communicated or required to be communicated to the audit committee and that (i) relates to accounts or disclosures that are material to the consolidated financial statements and (ii) involved our especially challenging, subjective, or complex judgments. The communication of critical audit matters does not alter in any way our opinion on the consolidated financial statements, taken as a whole, and we are not, by communicating the critical audit matter below, providing a separate opinion on the critical audit matter or on the accounts or disclosures to which it relates. Revenue Recognition - Identifying and Evaluating Terms and Conditions in Contracts As described in Note 1 to the consolidated financial statements, revenue recognition is determined by management through the following steps: (i) identification of the contract, or contracts, with the customer; (ii) identification of the performance obligations in the contract; (iii) determination of the transaction price; (iv) allocation of the transaction price to the performance obligation in the contract; and (v) recognition of the revenue when, or as, the Company satisfies a performance obligation. Management applies significant judgment in identifying and evaluating any terms and conditions in contracts which may impact revenue recognition. For the year ended January 31, 2022, the Company’s revenue was $2.11 billion. The principal considerations for our determination that performing procedures relating to revenue recognition, specifically identifying and evaluating terms and conditions in contracts, is a critical audit matter are the significant judgment by management in identifying and evaluating terms and conditions, especially non-standard terms, in contracts that impact revenue recognition. This in turn led to significant auditor judgment and effort in performing procedures and evaluating audit evidence to determine whether terms and conditions were appropriately identified and evaluated by management. Addressing the matter involved performing procedures and evaluating audit evidence in connection with forming our overall opinion on the consolidated financial statements. These procedures included testing the effectiveness of controls relating to the revenue recognition process, including controls related to the identification and evaluation of terms and conditions that impact the determination of revenue recognition. These procedures also included, among others, testing the completeness and accuracy of management’s identification and evaluation of the specific terms and conditions in contracts with customers by examining revenue contracts on a test basis and testing management’s process for identifying and evaluating the terms and conditions in contracts, including management’s determination of the impact of those terms and conditions on revenue recognition. /s/ PricewaterhouseCoopers LLP San Francisco, California March 25, 2022 We have served as the Company’s auditor since 2009, which includes periods before the Company became subject to SEC reporting requirements. DocuSign, Inc.| 2022 Form 10-K | 62 DOCUSIGN, INC. CONSOLIDATED BALANCE SHEETS January 31, (in thousands, except per share data) 2022 2021 Assets Current assets Cash and cash equivalents $ 509,059 $ 566,055 Investments—current 293,763 207,450 Accounts receivable, net of allowance for doubtful accounts of $ 5,807 and $ 5,362 as of January 31, 2022 and 2021 440,950 323,570 Contract assets—current 12,588 16,883 Prepaid expenses and other current assets 63,236 48,390 Total current assets 1,319,596 1,162,348 Investments—noncurrent 94,938 92,717 Property and equipment, net 184,664 165,039 Operating lease right-of-use assets 126,021 159,352 Goodwill 355,058 350,151 Intangible assets, net 98,816 121,828 Deferred contract acquisition costs—noncurrent 311,835 260,130 Other assets—noncurrent 50,337 24,942 Total assets $ 2,541,265 $ 2,336,507 Liabilities and Equity Current liabilities Accounts payable $ 52,804 $ 37,367 Accrued expenses and other current liabilities 91,377 66,566 Accrued compensation 160,163 156,158 Convertible senior notes—current — 20,469 Contract liabilities—current 1,029,891 779,642 Operating lease liabilities—current 37,404 32,971 Total current liabilities 1,371,639 1,093,173 Convertible senior notes, net—noncurrent 718,487 693,219 Contract liabilities—noncurrent 16,725 16,492 Operating lease liabilities—noncurrent 126,340 165,704 Deferred tax liability—noncurrent 9,316 6,464 Other liabilities—noncurrent 23,255 32,328 Total liabilities 2,265,762 2,007,380 Commitments and contingencies (Note 10) Convertible senior notes (Note 8) — 3,390 Stockholders’ equity Preferred stock, $ 0.0001 par value; 10,000 shares authorized, 0 shares issued and outstanding as of January 31, 2022 and 2021 — — Common stock, $ 0.0001 par value; 500,000 shares authorized, 198,834 shares outstanding as of January 31, 2022; 500,000 shares authorized, 192,807 shares outstanding as of January 31, 2021 20 19 Treasury stock, at cost: 7 shares as of January 31, 2022; 5 shares as of January 31, 2021 ( 1,532 ) ( 1,048 ) Additional paid-in capital 1,720,013 1,702,254 Accumulated other comprehensive income (loss) ( 4,809 ) 4,964 Accumulated deficit ( 1,438,189 ) ( 1,380,452 ) Total stockholders’ equity 275,503 325,737 Total liabilities and equity $ 2,541,265 $ 2,336,507 The accompanying notes are an integral part of these consolidated financial statements. DocuSign, Inc.| 2022 Form 10-K | 63 DOCUSIGN, INC. CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS Year Ended January 31, (in thousands, except per share data) 2022 2021 2020 Revenue: Subscription $ 2,037,272 $ 1,381,397 $ 918,463 Professional services and other 69,941 71,650 55,508 Total revenue 2,107,213 1,453,047 973,971 Cost of revenue: Subscription 343,661 259,992 163,931 Professional services and other 122,790 104,066 79,303 Total cost of revenue 466,451 364,058 243,234 Gross profit 1,640,762 1,088,989 730,737 Operating expenses: Sales and marketing 1,076,527 798,625 591,379 Research and development 393,362 271,522 185,552 General and administrative 232,757 192,697 147,315 Total operating expenses 1,702,646 1,262,844 924,246 Loss from operations ( 61,884 ) ( 173,855 ) ( 193,509 ) Interest expense ( 6,443 ) ( 30,799 ) ( 29,254 ) Loss on extinguishment of debt — ( 33,752 ) — Interest income and other income, net 1,413 8,914 19,207 Loss before provision for income taxes ( 66,914 ) ( 229,492 ) ( 203,556 ) Provision for income taxes 3,062 13,775 4,803 Net loss $ ( 69,976 ) $ ( 243,267 ) $ ( 208,359 ) Net loss per share attributable to common stockholders, basic and diluted $ ( 0.36 ) $ ( 1.31 ) $ ( 1.18 ) Weighted-average number of shares used in computing net loss per share attributable to common stockholders, basic and diluted 196,675 185,760 176,704 Other comprehensive income (loss): Foreign currency translation gains (losses), net of tax $ ( 7,935 ) $ 7,468 $ ( 573 ) Unrealized gains (losses) on investments, net of tax ( 1,838 ) ( 831 ) 865 Other comprehensive income (loss) ( 9,773 ) 6,637 292 Comprehensive loss $ ( 79,749 ) $ ( 236,630 ) $ ( 208,067 ) Stock-based compensation expense included in costs and expenses: Cost of revenue—subscription $ 31,152 $ 20,793 $ 12,882 Cost of revenue—professional services and other 27,347 21,865 15,703 Sales and marketing 186,759 131,041 94,863 Research and development 108,523 65,890 43,211 General and administrative 54,761 47,288 39,745 The accompanying notes are an integral part of these consolidated financial statements. DocuSign, Inc.| 2022 Form 10-K | 64 DOCUSIGN, INC. CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY Common Stock Additional Paid-In Capital Treasury Stock Accumulated Other Comprehensive Income (Loss) Accumulated Deficit Total Stockholders’ Equity (in thousands) Shares Amount Balances at January 31, 2019 169,303 $ 17 $ 1,545,088 $ — $ ( 1,965 ) $ ( 928,778 ) $ 614,362 Exercise of stock options 6,737 1 72,176 — — — 72,177 Settlement of restricted stock units 4,706 — — — — — — Tax withholding on net share settlement of restricted stock units — — ( 166,504 ) — — — ( 166,504 ) Employee stock purchase plan 508 — 23,872 — — — 23,872 Employee stock-based compensation expense — — 210,535 — — — 210,535 Net loss — — — — — ( 208,359 ) ( 208,359 ) Cumulative impact of Topic 842 adoption — — — — — ( 48 ) ( 48 ) Other comprehensive income, net — — — — 292 — 292 Balances at January 31, 2020 181,254 18 1,685,167 — ( 1,673 ) ( 1,137,185 ) 546,327 Settlement of convertible senior notes due in 2023 4,698 1 ( 31,933 ) — — — ( 31,932 ) Reclassification to mezzanine equity for convertible senior notes due in 2023 — — ( 3,390 ) — — — ( 3,390 ) Equity component of issued convertible senior notes due in 2024 — — 63,268 — — — 63,268 Purchase of capped calls related to issuance of convertible senior notes due in 2024 — — ( 31,395 ) — — — ( 31,395 ) Issuance of common stock as consideration for acquisition 247 — 48,361 — — — 48,361 Exercise of stock options 2,072 — 24,305 — — — 24,305 Settlement of restricted stock units 4,072 — — — — — — Tax withholding on net share settlement of restricted stock units and employee stock purchase plan — — ( 376,542 ) ( 1,048 ) — — ( 377,590 ) Employee stock purchase plan 464 — 29,859 — — — 29,859 Employee stock-based compensation expense — — 294,554 — — — 294,554 Net loss — — — — — ( 243,267 ) ( 243,267 ) Other comprehensive income, net — — — — 6,637 — 6,637 Balances at January 31, 2021 192,807 $ 19 $ 1,702,254 $ ( 1,048 ) $ 4,964 $ ( 1,380,452 ) $ 325,737 The accompanying notes are an integral part of these consolidated financial statements. DocuSign, Inc.| 2022 Form 10-K | 65 DOCUSIGN, INC. CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (Continued) Common Stock Additional Paid-In Capital Treasury Stock Accumulated Other Comprehensive Income (Loss) Accumulated Deficit Total Stockholders’ Equity (in thousands) Shares Amount Balances at January 31, 2021 192,807 19 1,702,254 ( 1,048 ) 4,964 ( 1,380,452 ) 325,737 Cumulative impact of Accounting Standards Update 2020-06 adoption — — ( 86,144 ) — — 12,239 ( 73,905 ) Settlement of convertible senior notes due in 2023 749 — ( 873 ) — — — ( 873 ) Exercise of stock options 1,693 — 23,729 — — — 23,729 Settlement of restricted stock units and employee stock purchase plan 5,071 1 ( 1 ) — — — — Tax withholding on net share settlement of restricted stock units and employee stock purchase plan ( 1,760 ) — ( 388,915 ) ( 484 ) — — ( 389,399 ) Employee stock purchase plan 264 — 46,077 — — — 46,077 Charitable donation of common stock 10 — 3,000 — — — 3,000 Employee stock-based compensation expense — — 420,886 — — — 420,886 Net loss — — — — — ( 69,976 ) ( 69,976 ) Other comprehensive loss, net — — — — ( 9,773 ) — ( 9,773 ) Balances at January 31, 2022 198,834 $ 20 $ 1,720,013 $ ( 1,532 ) $ ( 4,809 ) $ ( 1,438,189 ) $ 275,503 The accompanying notes are an integral part of these consolidated financial statements. DocuSign, Inc.| 2022 Form 10-K | 66 DOCUSIGN, INC. CONSOLIDATED STATEMENTS OF CASH FLOWS Year Ended January 31, (in thousands) 2022 2021 2020 Cash flows from operating activities: Net loss $ ( 69,976 ) $ ( 243,267 ) $ ( 208,359 ) Adjustments to reconcile net loss to net cash provided by operating activities Depreciation and amortization 81,913 71,090 50,182 Amortization of deferred contract acquisition and fulfillment costs 144,442 99,384 69,747 Amortization of debt discount and transaction costs 5,098 28,001 26,389 Loss on extinguishment of debt — 33,752 — Operating cash flow related to repayments of convertible senior notes — ( 75,165 ) — Non-cash operating lease costs 26,819 26,728 19,435 Stock-based compensation expense 408,542 286,877 206,404 Deferred income taxes 1,369 ( 2,410 ) 1,287 Other 9,871 ( 210 ) ( 1,741 ) Changes in operating assets and liabilities Accounts receivable ( 117,380 ) ( 73,913 ) ( 63,293 ) Contract assets 4,893 1,912 ( 1,508 ) Prepaid expenses and other current assets ( 7,074 ) ( 1,155 ) ( 3,142 ) Deferred contract acquisition and fulfillment costs ( 207,393 ) ( 208,510 ) ( 115,723 ) Other assets ( 16,389 ) ( 6,006 ) 1,538 Accounts payable 12,148 12,128 3,849 Accrued expenses and other liabilities 10,828 37,155 9,353 Accrued compensation 1,128 64,586 5,636 Contract liabilities 250,482 267,750 130,266 Operating lease liabilities ( 32,854 ) ( 21,773 ) ( 14,624 ) Net cash provided by operating activities 506,467 296,954 115,696 Cash flows from investing activities: Cash paid for acquisition, net of acquired cash ( 6,388 ) ( 180,370 ) — Purchases of marketable securities ( 384,128 ) ( 164,989 ) ( 861,252 ) Sales of marketable securities 7,569 28,986 — Maturities of marketable securities 283,184 488,538 627,309 Purchases of strategic and other investments ( 1,750 ) ( 8,541 ) ( 15,500 ) Purchases of property and equipment ( 61,396 ) ( 82,395 ) ( 72,046 ) Net cash (used in) provided by investing activities ( 162,909 ) 81,229 ( 321,489 ) Cash flows from financing activities: Proceeds from issuance of convertible senior notes, net of initial purchasers' discounts and transaction costs — 677,370 — Purchase of capped calls related to issuance of convertible senior notes — ( 31,395 ) — Repayments of convertible senior notes ( 77,906 ) ( 384,199 ) — Payment of revolving credit facility costs — ( 2,453 ) — Payment of tax withholding obligation on RSU settlement and ESPP purchase ( 386,521 ) ( 372,463 ) ( 166,504 ) Proceeds from exercise of stock options 23,729 24,305 72,177 Proceeds from employee stock purchase plan 46,077 29,859 23,872 Net cash (used in) provided by financing activities ( 394,621 ) ( 58,976 ) ( 70,455 ) Effect of foreign exchange on cash, cash equivalents and restricted cash ( 5,594 ) 5,646 ( 447 ) Net increase (decrease) in cash, cash equivalents and restricted cash ( 56,657 ) 324,853 ( 276,695 ) Cash, cash equivalents and restricted cash at beginning of period 566,336 241,483 518,178 Cash, cash equivalents and restricted cash at end of period $ 509,679 $ 566,336 $ 241,483 The accompanying notes are an integral part of these consolidated financial statements. DocuSign, Inc.| 2022 Form 10-K | 67 DOCUSIGN, INC. CONSOLIDATED STATEMENTS OF CASH FLOWS (Continued) Year Ended January 31, (in thousands) 2022 2021 2020 Supplemental disclosure: Cash paid for interest $ 349 $ 78,040 $ 2,852 Cash paid for operating lease liabilities 40,552 35,176 22,034 Cash paid for income taxes 6,940 3,503 1,970 Non-cash investing and financing activities: Property and equipment in accounts payable and accrued expenses and other current liabilities $ 11,285 $ 3,903 $ 14,082 Operating lease right-of-use assets exchanged for lease obligations 2,749 30,816 77,391 Fair value of shares issued as consideration for acquisition — 48,361 — Fair value of shares issued as part of the repayments of convertible senior notes 174,230 1,233,990 — Derecognition of build-to-suit lease — — 2,479 The accompanying notes are an integral part of these consolidated financial statements. DocuSign, Inc.| 2022 Form 10-K | 68 DOCUSIGN, INC. NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Note 1 . 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, sign, act on and manage agreements, thereby simplifying and accelerating the process of doing business. Basis of Presentation and Principles of Consolidation Our consolidated financial statements include those of DocuSign, Inc. and our subsidiaries. All intercompany accounts and transactions have been eliminated in consolidation. The accompanying consolidated financial statements have been prepared in accordance with United States generally accepted accounting principles (“GAAP”). Our fiscal year ends on January 31. References to fiscal 2022, for example, are to the fiscal year ended January 31, 2022. Certain prior year amounts have been reclassified to conform to current year presentation. These amounts were not material to any of the periods presented. Use of Estimates The preparation of financial statements in conformity with U.S. GAAP requires management to make estimates and assumptions in the consolidated financial statements and notes thereto. Significant items subject to such estimates and assumptions made by management include, but are not limited to, the determination of: • the average period of benefit associated with deferred contract acquisition costs and fulfillment costs; • the valuation of strategic investments; • the fair value of certain stock awards issued; • the f air value of the liability and equity components of convertible notes; • the useful life and recoverability of long-lived assets; • the discount rate used for operating leases; and • the recognition, measurement and valuation of deferred income taxes. Since the emergence of the COVID-19 pandemic in March 2020, we have undertaken measures to protect our employees, partners and customers, including providing the majority of our employees the option to work remotely until at least January 31, 2023. However, there can be no assurance that these measures will be effective, that we will be able to adopt new measures as needed or that we will be able to discontinue these measures without adversely affecting our business operations. In addition, the COVID-19 pandemic and related recent developments (including the emergence of new coronavirus variants, the actions undertaken to contain the virus or mitigate its impacts, including actions mandated by governments and health authorities and changing public health directives or restrictions, vaccine efficacy against COVID-19 variants, current or future travel restrictions and how quickly and to what extent normal global economic and operating conditions can or will resume) have created and may continue to create significant uncertainty in global financial markets, which may decrease technology spending, depress demand for our products and harm our business and results of operations. As of the date of issuance of the financial statements, we are not aware of any specific event or circumstance that would require us to update our estimates or judgments or revise the carrying value of our assets or liabilities, except for certain subleases that resulted in an impairment of $ 5.1 million on operating lease right-of-use assets recorded during the twelve months ended January 31, 2022. These estimates may change as new events occur and additional information is obtained, which could be recognized in the consolidated financial statements as soon as they become known. Actual results could differ from those estimates and any such differences may be material to our financial statements. DocuSign, Inc.| 2022 Form 10-K | 69 Concentration of Credit Risk Our financial instruments that are exposed to concentrations of credit risk consist primarily of cash, cash equivalents, marketable securities and accounts receivable. Although we deposit our cash with multiple financial institutions, the deposits, at times, may exceed federally insured limits. We have not experienced any losses on our deposits of cash and cash equivalents. Cash equivalents consist of money market funds, which are invested through financial institutions in the U.S. Management believes that the institutions are financially stable and, accordingly, minimal credit risk exists. No customer individually accounted for more than 10% of our revenues in the years ended January 31, 2022, 2021 and 2020 or for more than 10% of our accounts receivable as of January 31, 2022 and 2021. We perform ongoing credit evaluations of our customers, do not require collateral and maintain allowances for potential credit losses on customers’ accounts using the expected loss model. Revenue Recognition We recognize revenue when a customer obtains control of promised services. We apply significant judgment in identifying and evaluating any terms and conditions in contracts which may impact revenue recognition. The amount of revenue recognized reflects the consideration that we expect to be entitled to receive in exchange for these services. To achieve the core principle of this standard, we apply the following steps: 1. Identification of the contract, or contracts, with the customer We consider the terms and conditions of the contract and our customary business practices in identifying our contracts under ASC 606. We determine we have a contract with a customer when the contract is approved, we can identify each party’s rights regarding the services to be transferred, we can identify the payment terms for the services, we have determined the customer has the ability and intent to pay and the contract has commercial substance. At contract inception we evaluate whether two or more contracts should be combined and accounted for as a single contract and whether the combined or single contract includes more than one performance obligation. We apply judgment in determining the customer’s ability and intent to pay, which is based on a variety of factors, including the customer’s historical payment experience or, in the case of a new customer, credit and financial information pertaining to the customer. 2. Identification of the performance obligations in the contract Performance obligations promised in a contract are identified based on the services and the products that will be transferred to the customer that are both capable of being distinct, whereby the customer can benefit from the service either on its own or together with other resources that are readily available from third parties or from us, and are distinct in the context of the contract, whereby the transfer of the services and the products is separately identifiable from other promises in the contract. Our performance obligations consist of (i) subscription services, (ii) professional services, (iii) on-premises solutions, and (iv) maintenance and support for on-premises solutions. 3. Determination of the transaction price The transaction price is determined based on the consideration to which we expect to be entitled in exchange for transferring services to the customer. Variable consideration is included in the transaction price if, in our judgment, it is probable that a significant future reversal of cumulative revenue under the contract will not occur. None of our contracts contain a significant financing component. 4. Allocation of the transaction price to the performance obligation in the contract If the contract contains a single performance obligation, the entire transaction price is allocated to the single performance obligation. Contracts that contain multiple performance obligations require an allocation of the transaction price to each performance obligation based on a relative standalone selling price ("SSP"). 5. Recognition of the revenue when, or as, we satisfy a performance obligation Revenue is recognized at the time the related performance obligation is satisfied by transferring the control of the promised service to a customer. Revenue is recognized as control of the service is transferred to the customer, in an amount that reflects the consideration that we expect to receive in exchange for those services. We generate all our revenue from contracts with customers. DocuSign, Inc.| 2022 Form 10-K | 70 Subscription Revenue We generate revenue primarily from sales of subscriptions to access our software platform and related subscriptions of our customers. Our subscription revenue is driven by our go-to-market model, which includes a combination of direct sales, partner-assisted sales and web-based self-service purchasing. Subscription arrangements with customers do not provide the customer with the right to take possession of our software operating platform at any time. Instead, customers are granted continuous access to our software platform over the contractual period. A time-elapsed method is used to measure progress because we transfer control evenly over the contractual period. Accordingly, the fixed consideration related to subscription revenue is generally recognized on a straight-line basis over the contract term beginning on the date access to our software platform is provided. Professional Services and Other Revenue Professional services and other revenue consists of fees associated with consulting and training services from assisting customers in implementing and expanding the use of our software platform. These services are generally distinct from subscription services. Professional services do not result in significant customization of the subscription service. Revenue from professional services provided on a time and materials basis is recognized as the services are performed. Other revenue includes amounts derived from the sale of our on-premises solutions, which are recognized upon passage of control, which occurs upon shipment of the product. The maintenance and support on the on-premises solutions is a stand-ready obligation to perform this service over the term of the arrangement and, as a result, is accounted for ratably over the term of the arrangement. Contracts with Multiple Performance Obligations Most of our contracts with customers contain multiple performance obligations that are distinct and accounted for separately. The transaction price is allocated to the separate performance obligations on a relative SSP basis. We determine SSP for our performance obligations based on our observable inputs, such as standalone sales and historical contract pricing. SSP is consistent with our overall pricing objectives, taking into consideration the type of subscription services and professional and other services. Variable Consideration Revenue from sales is recorded at the net sales price, which is the transaction price, and includes estimates of variable consideration. The amount of variable consideration that is included in the transaction price is constrained and is included in the net sales price only to the extent that it is probable that a significant reversal in the amount of the cumulative revenue will not occur when the uncertainty is resolved. If our services do not meet certain service level commitments, our customers are entitled to receive service credits, and in certain cases, refunds, each representing a form of variable consideration. We have historically not experienced any significant incidents affecting the defined levels of reliability and performance as required by our subscription contracts. Accordingly, the amount of any estimated refunds related to these agreements in the consolidated financial statements is not material during the periods presented. Deferred Contract Acquisition Costs We capitalize sales commissions, certain parts of the company bonus and associated payroll taxes paid to internal sales personnel that are incremental to the acquisition of customer contracts as deferred contract acquisition costs in "Prepaid expenses and other current assets" and "Deferred contract acquisition costs—noncurrent" on our consolidated balance sheets. We determine whether costs should be deferred based on our sales compensation plans, if the commissions are in fact incremental and would not have occurred absent the customer contract. These deferred commissions are amortized on a straight-line basis over the periods of benefit, commensurate with the pattern of revenue recognition. Commissions paid for renewal of a subscription contract are not considered commensurate with the commissions paid for the acquisition of the initial subscription contract given the substantive difference in commission rates between new and renewal contracts. The period of benefit for commissions paid for the acquisition of the initial subscription contract, of five years , is determined by taking into consideration our initial estimated customer life and the technological life of our software platform and related significant features. The period of benefit for renewal subscription contracts, of two years , is determined by considering the average contractual term for renewal contracts. DocuSign, Inc.| 2022 Form 10-K | 71 Commissions paid on professional services contracts are amortized over the period of benefit, being the period the associated revenue is earned as the commissions paid on new and renewal professional services contracts are commensurate with each other. Amortization of deferred contract acquisition costs is primarily included in the “Sales and marketing” expense in the consolidated statements of operations and comprehensive loss. We periodically review these deferred costs to determine whether events or changes in circumstances have occurred that could impact the period of benefit of these deferred contract acquisition costs. There were no material impairment losses recorded during the periods presented. Deferred Contract Fulfillment Costs We capitalize third-party costs to fulfill contracts with a customer in “Prepaid expenses and other current assets” and “Other assets—noncurrent” on our consolidated balance sheets. We amortize these costs on a straight-line basis consistent with the ratable revenue recognition of the performance obligations in the associated contracts. Cost of Revenue “Subscription” cost of revenue primarily consists of personnel and related costs to support our software platform, amortization expense associated with capitalized internally-developed software and technology-related intangible assets, property and equipment depreciation, allocated overhead expenses, merchant processing fees and server hosting costs. “Professional services and other” cost of revenue consists primarily of personnel costs for our professional services delivery team, travel-related costs and allocated overhead. Advertising Advertising costs are expensed as incurred and are included in “Sales and marketing” expense in our consolidated statements of operations and comprehensive loss. Advertising expense was $ 115.7 million, $ 78.6 million and $ 41.6 million in the years ended January 31, 2022, 2021 and 2020. Research and Development Research and development costs are expensed as incurred and consist primarily of personnel costs, including salaries, bonuses and benefits, and stock-based compensation. Stock-Based Compensation Compensation cost for stock-based awards issued to employees, including stock options, employee stock purchase plan (“ESPP”) purchase rights and restricted stock units (“RSUs”), is measured at fair value on the date of grant and recognized over the service period, generally on a straight-line basis. The fair value of stock options and ESPP purchase rights is estimated on the date of grant using a Black-Scholes option-pricing model. The fair value of RSUs is estimated on the date of grant based on the fair value of our underlying common stock. From time to time, we grant RSUs that also include performance-based or market-based conditions. For RSUs granted with a market condition, we use a lattice model simulation analysis to value the RSUs. Compensation expense for RSUs granted prior to January 31, 2018, is recognized on a graded basis over the requisite service period. Such RSUs contain a performance condition in the form of a specified liquidity event which was satisfied upon the effectiveness of our registration statement on Form S-1 (“IPO Registration Statement”) on April 26, 2018. RSUs granted after January 31, 2018, generally vest only on the satisfaction of service-based condition. Compensation expense for RSUs granted with a market or a performance condition is recognized on a graded vesting basis over the requisite service period. The amount of compensation expense related to the RSUs granted with a performance condition is determined after assessing the probability of achieving requisite performance criteria. We recognize compensation expense related to shares issued pursuant to the 2018 ESPP on a straight-line basis over the offering period of six months . DocuSign, Inc.| 2022 Form 10-K | 72 Compensation expense is recognized net of forfeitures that are estimated at the time of grant and revised in subsequent periods if actual forfeitures differ from those estimates. We capitalize stock-based compensation costs incurred as a result of qualifying internally-developed software development activities. We may elect to issue shares on the settlement dates net of the statutory tax withholding requirements to be paid by us on behalf of our employees. In these instances, we record the liability for withholding amounts to be paid by us as treasury stock or as a reduction to additional paid-in capital, and include these payments as a reduction of cash flows from financing activities. Income Taxes We use the asset and liability method of accounting for income taxes. Under this method, income tax expense is recognized for the amount of taxes payable or refundable for the current year. In addition, deferred tax assets and liabilities are recognized for expected future tax consequences of temporary differences between the financial reporting and tax basis of assets and liabilities, and for operating losses and tax credit carryforwards. We record a valuation allowance to reduce our deferred tax assets to an amount for which realization is more likely than not. Foreign Currency The functional currency of our foreign entities and branches is generally the local currency. Monetary assets and liabilities and transactions denominated in currencies other than an entity's functional currency are remeasured into its functional currency using current exchange rates at each balance sheet date. Nonmonetary assets and liabilities are not remeasured. We recognize gains and losses from such adjustments within “Interest income and other income, net” in the consolidated statements of operations and comprehensive loss in the period of occurrence. We present our financial statements in U.S. dollars. Adjustments resulting from translating foreign functional currency financial statements into U.S. dollars are recorded as a separate component on our consolidated statements of comprehensive loss, net of tax. All assets and liabilities denominated in a foreign currency are translated at the exchange rate on the balance sheet date. Revenues and expenses are translated at the average exchange rate during the period. Equity transactions are translated using the historical exchange rate. Net Loss Per Share Attributable to Common Stockholders In periods when we have net income, we compute basic and diluted net loss per share in conformity with the two-class method required for participating securities. The undistributed earnings are allocated between common stock and participating securities as if all earnings had been distributed during the period presented. We consider any shares issued on the early exercise of stock options subject to repurchase to be participating securities because holders of such shares have non-forfeitable dividend rights in the event a dividend is paid on common stock. The holders of early exercised shares do not have a contractual obligation to share in our losses. As such, our net losses in all the years presented were not allocated to these participating securities. Basic net loss per share attributable to common stockholders is computed by dividing the net loss attributable to common stockholders by the weighted-average number of shares of common stock outstanding during the period. Diluted net loss per share attributable to common stockholders is computed by giving effect to all potential shares of common stock, including shares underlying our convertible senior notes, unvested RSUs, early exercised or outstanding stock options, ESPP purchase rights, convertible preferred stock, and warrants to purchase common stock and convertible preferred stock, to the extent they are dilutive. Since we have reported net losses for all periods presented, dilutive common shares are not assumed to have been issued as their effect would have been antidilutive. Therefore, diluted net loss per share attributable to common stockholders is the same as basic net loss per share attributable to common stockholders. Cash and Cash Equivalents Cash and cash equivalents consist of money market funds, highly liquid investments with original maturities of three months or less at the date of purchase and deposits with financial institutions and are carried at fair value. DocuSign, Inc.| 2022 Form 10-K | 73 Investments Investments in marketable securities consist of commercial paper, corporate notes and bonds, as well as U.S. Treasury and government agency securities. Management determines the appropriate classification of investments at the time of purchase and reevaluates such determination at each balance sheet date. Marketable securities are classified as available-for-sale and are carried at fair value in the consolidated balance sheet and are classified as short-term or long-term based on their remaining contractual maturities. We evaluate our investments with unrealized loss positions at the individual security level to determine whether the unrealized loss was related to credit or noncredit factors. We consider whether a credit loss exists based on the extent of the unrealized loss position, any adverse conditions specifically related to the security or the issuer's operating environment, pay structure of the security, the issuer's payment history and any changes in the issuer's credit rating. Estimated credit losses are determined using a discounted cash flow model and recorded as an allowance, with changes in expected credit losses on our investments recorded in “Interest income and other income, net” in the consolidated statements of operations and comprehensive loss. Unrealized gains and losses related to noncredit factors are reflected in “Accumulated other comprehensive income (loss)” on the consolidated balance sheets. Prior to February 1, 2020, we evaluated our investments to assess whether those with unrealized loss positions were other than temporarily impaired. We considered impairments to be other than temporary if they were related to deterioration in credit risk or if it is likely we will sell the securities before the recovery of their cost basis. Realized gains and losses and declines in value judged to be other than temporary were determined based on the specific identification method and reported in “Interest income and other income, net” in the consolidated statements of operations and comprehensive loss. Strategic Investments Our strategic investments consist of non-marketable equity investments in privately-held companies and investment companies in which we do not have a controlling interest or significant influence. We have elected to apply the measurement alternative for equity investments in privately-held companies 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. We have elected to measure our equity investments in investment companies that do not have readily determinable fair values based on the investment’s net asset value. An impairment loss is recorded when an event or circumstance indicates a decline in value has occurred. As of January 31, 2022 and 2021, we held equity investments in privately-held companies totaling $ 12.4 million and $ 6.0 million that are classified in “Other assets—noncurrent” on our consolidated balance sheets. Restricted Cash Restricted cash consists of certificates of deposits collateralizing our operating lease agreements for office space and cash withheld from employees to fund claims and program expenses related to the Voluntary Disability Plans in California and Washington. The following table illustrates the reconciliation of cash, cash equivalents, and restricted cash shown in the consolidated statements of cash flows as of January 31, 2022, 2021, and 2020: January 31, (in thousands) 2022 2021 2020 Cash and cash equivalents $ 509,059 $ 566,055 $ 241,203 Restricted cash included in prepaid expense and other current assets 280 — 280 Restricted cash included in other assets - noncurrent 340 281 — Total cash, cash equivalents, and restricted cash $ 509,679 $ 566,336 $ 241,483 DocuSign, Inc.| 2022 Form 10-K | 74 Fair Value of Financial Instruments We measure assets and liabilities at fair value based on an expected exit price, which represents the amount that would be received on the sale of an asset or paid to transfer a liability in an orderly transaction between market participants. As such, fair value may be based on assumptions that market participants would use in pricing an asset or liability. The authoritative guidance on fair value measurements establishes a consistent framework for measuring fair value on either a recurring or nonrecurring basis whereby inputs, used in valuation techniques, are assigned a hierarchical level. The following are the hierarchical levels of inputs to measure fair value: Level 1 Observable inputs that reflect quoted prices (unadjusted) for identical assets or liabilities in active markets. Level 2 Inputs reflect quoted prices for identical assets or liabilities in markets that are not active; quoted prices for similar assets or liabilities in active markets; inputs other than quoted prices that are observable for the assets or liabilities; or inputs that are derived principally from or corroborated by observable market data by correlation or other means. Level 3 Unobservable inputs reflecting our own assumptions incorporated in valuation techniques used to determine fair value. These assumptions are required to be consistent with market participant assumptions that are reasonably available Assets and liabilities are classified in their entirety based on the lowest level of input that is significant to the fair value measurement. Our assessment of the significance of a particular input to the fair value measurement requires judgment and may affect the placement of assets and liabilities being measured within the fair value hierarchy. The carrying values of cash, accounts receivable and accounts payable approximate their respective fair values due to the short period of time to maturity, receipt or payment. Accounts Receivable and Allowance for Doubtful Accounts Accounts receivable primarily consist of amounts billed currently due from customers. Our accounts receivable are subject to collection risk. Gross accounts receivable are reduced for this risk by an allowance for doubtful accounts. This allowance is for estimated losses resulting from the inability of our customers to make required payments. Our allowance for doubtful accounts includes balances that are specifically identified for adequacy based on a regular evaluation of such factors as age of the receivable balance, current economic conditions, credit quality of the customer, and past collection experience. We also include in our allowance for doubtful accounts an estimate for future credit losses, based on historical experience, which is recorded in the period in which we invoice our customers starting February 1, 2020. We do not have any off-balance-sheet credit exposure related to our customers. We do not typically offer right of refund in our contracts and do not require collateral from our customers. Changes in the allowance for doubtful accounts were not material in all periods presented. Property and Equipment Property and equipment, including costs incurred to bring to the location and condition necessary for intended use, are recorded at cost and depreciated over their estimated useful lives using the straight-line method and the following estimated useful lives: Estimated Useful Life Computer and network equipment 3 years Software, including capitalized software development costs 3 - 5 years Furniture and office equipment 3 - 4 years Leasehold improvements Lesser of lease term and 10 years Disposals are removed at cost less accumulated depreciation, and any gain or loss from disposition is reflected in the statement of operations and comprehensive loss in the year of disposition. Additions and improvements that increase the value or extend the life of an asset are capitalized. Maintenance and repairs are expensed as incurred. DocuSign, Inc.| 2022 Form 10-K | 75 Leases On February 1, 2019, we adopted Accounting Standards Update (“ASU”) No. 2016-02, Leases (Topic 842) using the modified retrospective approach and applied the related optional practical expedients. 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. We do not recognize right-of-use assets and liabilities for leases with a term of twelve months or less. Additionally, we do not separate nonlease components from the associated lease components for our office leases and certain other asset classes. The total consideration includes fixed payments and contractual escalation provisions. We are responsible for maintenance, insurance, property taxes and other variable payments, which are expensed as incurred. Our leases include options to renew or terminate. We include the option to renew or terminate in our determination of the lease term when the option is deemed to be reasonably assured to be exercised. Operating leases are classified in “Operating lease right-of-use assets”, “Operating lease liabilities—current”, and “Operating lease liabilities—noncurrent” on our consolidated balance sheets. Operating lease expense is recognized on a straight-line basis over the expected lease term and included in “Loss from operations” in our consolidated statements of operations and comprehensive loss. Goodwill Goodwill represents the excess of the purchase price over the fair value of net assets acquired in business combinations accounted for using the acquisition method of accounting and is not amortized. We test goodwill for impairment at least annually, in the fourth quarter of each year, or as events occur or circumstances change that would more likely than not reduce the fair value of a reporting unit below its carrying amount. Such events and changes may include: significant changes in performance relative to expected operating results, significant changes in asset use, significant negative industry or economic trends, and changes in our business strategy. Our test for goodwill impairment starts with a qualitative assessment to determine whether it is necessary to perform the quantitative goodwill impairment test. If qualitative factors indicate that the fair value of the reporting unit is more likely than not less than its carrying amount, then a quantitative goodwill impairment test is performed. For the purposes of impairment testing, we have determined that we have one operating segment and one reporting unit. We performed qualitative assessment for the fiscal year ended January 31, 2022, and concluded that it is more likely than not that the fair value of the reporting unit significantly exceeds its carrying value. There was no impairment of goodwill recorded in the years ended January 31, 2021 and 2020. Intangible Assets Intangible assets with finite lives are amortized using the straight-line method over their estimated useful lives. The estimated useful lives of intangible assets, estimated based on our expected period of benefit, are as follows: Estimated Useful Life Existing technology 3 - 5 years Customer contracts & related relationships 5 - 10 years Other (1) 1 - 5 years (1) Includes certifications, maintenance contracts and related relationships, subscription backlog and tradenames and trademarks DocuSign, Inc.| 2022 Form 10-K | 76 We evaluate the estimated remaining useful lives of intangible assets and other long-lived assets to assess whether a revision to the remaining periods of amortization is required. Impairment of Long-Lived Assets We review long-lived assets, including property and equipment and intangible assets, for impairment whenever events or changes in business circumstances indicate that the carrying amount of the asset group may not be fully recoverable. An impairment loss is recognized when estimated undiscounted future cash flows expected to result from the use of the asset and its eventual disposition are less than its carrying amount. We recognized an impairment of $ 5.1 million on operating lease right-of-use assets as part of General and administrative expense during the year ended January 31, 2022. There was no impairment recognized in the other periods presented. Software Development and Cloud Computing Arrangement Implementation Costs We capitalize qualifying internally-developed software development costs incurred during the application development stage, as long as it is probable the project will be completed and the software will be used to perform the function intended. Capitalization of such costs ceases once the project is substantially complete and ready for its intended use. Capitalized software development costs are included in “Property and equipment, net” on our consolidated balance sheets and are amortized on a straight-line basis over their expected useful lives of approximately three to five years . We also capitalize qualifying implementation costs under cloud computing arrangements (“CCA”). Capitalization of such costs ceases once the software of the hosting arrangement is ready for its intended use. The CCA implementation costs balance was $ 22.6 million and $ 4.3 million as of January 31, 2022 and 2021, and is included in “Other assets—noncurrent” on our consolidated balance sheets and amortized on a straight-line basis over the term of the associated hosting arrangement. Business Combinations We account for our acquisitions using the acquisition method of accounting, which requires, among other things, allocation of the fair value of purchase consideration to the tangible and intangible assets acquired and liabilities assumed at their estimated fair values on the acquisition date. The excess of the fair value of purchase consideration over the values of these identifiable assets and liabilities is recorded as goodwill. Management’s estimates of fair value are based upon assumptions believed to be reasonable, but which are inherently uncertain. During the measurement period, not to exceed one year from the date of acquisition, we may record adjustments to the assets acquired and liabilities assumed, with a corresponding offset to goodwill if new information is obtained related to facts and circumstances that existed as of the acquisition date. After the measurement period, any subsequent adjustments are reflected in the consolidated statements of operations and comprehensive loss. Acquisition costs, such as legal and consulting fees, are expensed as incurred. Segments Operating segments are defined as components of an entity for which separate financial information is available and that is regularly reviewed by our Chief Operating Decision Maker (“CODM”) in deciding how to allocate resources to an individual segment and in assessing performance. Our Chief Executive Officer is our CODM. Our CODM reviews financial information presented on a consolidated basis for purposes of making operating decisions, allocating resources, and evaluating financial performance. As such, we have determined that we operate in one operating and one reportable segment. Convertible Debt Prior to February 1, 2021, we accounted for our convertible debt instruments 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 based on comparable convertible transactions for similar companies. The carrying amount of the equity component representing the conversion option was calculated by deducting the fair value of the liability component from the principal amount of the convertible debt instruments as a whole. This difference represented a debt discount that was amortized to interest expense over the term of the convertible debt instruments using the effective interest rate method. The equity component was not remeasured as long as it continued to meet the conditions for equity classification. DocuSign, Inc.| 2022 Form 10-K | 77 The transaction costs incurred related to the issuance of the convertible debt instruments were allocated to the liability and equity components based on their relative initial carrying value of the convertible debt instruments. Transaction costs attributable to the liability component were being amortized to interest expense over the respective terms of the convertible debt instruments, and transaction costs attributable to the equity component were netted against the equity component of the convertible debt instruments in stockholders’ equity. Effective February 1, 2021, we account for our convertible debt instruments as a single liability measured at its amortized cost. See “Recently Adopted Accounting Pronouncements” below. At issuance, the carrying amount is calculated as the proceeds, net of initial purchasers’ discounts and transaction costs. The difference between the principal amount and carrying value is amortized to interest expense over the term of the convertible debt instruments using the effective interest rate method. At settlement, the carrying amount of the liability is derecognized and the excess of the cash consideration, if any, over the carrying amount is recorded as a reduction to additional paid-in capital. Capped calls entered into in connection with the offering of the convertible debt instruments are considered indexed to our own stock and are considered equity classified. They are recorded in stockholders’ equity and are not accounted for as derivatives. The cost incurred in connection with the capped calls was recorded as a reduction to additional paid-in capital. Legal Contingencies We evaluate contingent liabilities including threatened or pending litigation and make provisions for such liabilities when it is both probable that a loss has been incurred and its amount can be reasonably estimated. We periodically assess the likelihood of any adverse judgments or outcomes from potential claims or legal proceedings, as well as potential ranges of probable losses, when the outcomes of the claims or proceedings are probable and reasonably estimable. A determination of the amount of the liabilities required, if any, for these contingencies is made after the analysis of each separate matter. Recently Adopted Accounting Pronouncements On February 1, 2021, we early adopted ASU No. 2020-06, Debt—Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging—Contracts in Entity’s Own Equity (Subtopic 815-40) using the modified retrospective approach. This ASU removes separation models for convertible debt with a cash conversion feature and convertible instruments with a beneficial conversion feature. Such convertible debt is accounted for as a single liability measured at its amortized cost and convertible preferred stock will be accounted for as a single equity instrument measured at its historical cost, as long as no other features require bifurcation and recognition as derivatives. The ASU also requires the if-converted method to be used for convertible instruments and the effect of potential share settlement be included in the diluted earnings per share calculation when an instrument may be settled in cash or shares. The adoption of the ASU using the modified retrospective method resulted in: • an increase of $ 77.3 million to the total carrying value of our convertible senior notes to reflect the full principal amount of the convertible notes outstanding net of issuance costs, • reductions of $ 86.1 million to additional paid-in capital and $ 3.4 million to mezzanine equity to remove the equity component separately recorded for the conversion features associated with the convertible notes, and • a cumulative-effect adjustment of $ 12.2 million to the beginning balance of accumulated deficit as of February 1, 2021. Note 2. Revenue Subscription revenue is recognized over time and accounted for approximately 97 %, 95 % and 94 % of our revenue for the years ended January 31, 2022, 2021 and 2020. Performance Obligations As of January 31, 2022, the amount of the transaction price allocated to remaining performance obligations for contracts greater than one year was $ 1.6 billion. We expect to recognize 53 % of the transaction price allocated to remaining performance obligations within the 12 months following January 31, 2022 in our consolidated statement of operations and comprehensive loss. DocuSign, Inc.| 2022 Form 10-K | 78 Contract Balances Contract assets represent amounts for which we have recognized revenue, pursuant to our revenue recognition policy, for contracts that have not yet been invoiced to our customers where there is a remaining performance obligation, typically for multi-year arrangements. Total contract assets were $ 12.6 million and $ 17.5 million as of January 31, 2022 and 2021. The change in contract assets reflects the difference in timing between our satisfaction of remaining performance obligations and our contractual right to bill our customers. Contract liabilities consist of deferred revenue and include payments received in advance of performance under the contract. Such amounts are generally recognized as revenue over the contractual period. For the years ended January 31, 2022 , 2021 and 2020, we recognized revenue of $ 773.7 million , $ 499.5 million and $ 374.8 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. Note 3 . Fair Value Measurements The following table summarizes our financial assets that are measured at fair value on a recurring basis: January 31, 2022 (in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Level 1: Cash equivalents (1) Money market funds $ 110,716 $ — $ — $ 110,716 Level 2: Cash equivalents (1) Commercial paper 3,499 — — 3,499 Available-for-sale securities Commercial paper 126,371 1 ( 175 ) 126,197 Corporate notes and bonds 243,840 — ( 1,296 ) 242,544 U.S. governmental securities 20,036 — ( 76 ) 19,960 Level 2 total 393,746 1 ( 1,547 ) 392,200 Total $ 504,462 $ 1 $ ( 1,547 ) $ 502,916 DocuSign, Inc.| 2022 Form 10-K | 79 January 31, 2021 (in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Level 1: Cash equivalents (1) Money market funds $ 284,312 $ — $ — $ 284,312 Level 2: Available-for-sale securities Commercial paper 42,048 1 ( 23 ) 42,026 Corporate notes and bonds 199,277 375 ( 67 ) 199,585 U.S. government securities 58,050 12 ( 6 ) 58,056 Level 2 total 299,375 388 ( 96 ) 299,667 Level 3: Available-for-sale securities Corporate notes and bonds 500 — — 500 Total $ 584,187 $ 388 $ ( 96 ) $ 584,479 (1) Included in "cash and cash equivalents" in our consolidated balance sheets as of January 31, 2022 and 2021, in addition to cash of $ 394.9 million and $ 281.7 million We use quoted prices in active markets for identical assets to determine the fair value of our Level 1 investments. The fair value of our Level 2 investments is determined using pricing based on quoted market prices or alternative market observable inputs . The fair value of our Level 3 investments is determined based on an income approach using unobservable inputs. The fair value of our available-for-sale securities as of January 31, 2022, by remaining contractual maturities, were as follows (in thousands): Due in one year or less $ 293,763 Due in one to two years 94,938 $ 388,701 As of January 31, 2022 and 2021, securities in an unrealized loss position were, individually and in aggregate, not material. An allowance for credit losses was deemed unnecessary for these securities, given the extent of the unrealized loss positions as well as the issuers' high credit ratings and consistent payment history. We had no liabilities measured at fair value on a recurring basis as of January 31, 2022 and 2021. Strategic Investments During the year ended January 31, 2022, investments in equity securities without readily determinable fair values increased by $ 4.8 million due to adjustments related to observable price changes that occurred primarily during the three months ended April 30, 2021. During the year ended January 31, 2021, there were no material observable price changes. Convertible Senior Notes 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—noncurrent” and “Convertible senior notes—current.” Refer to Note 8 for further information. DocuSign, Inc.| 2022 Form 10-K | 80 January 31, (in thousands) 2022 2021 0.5 % Convertible Senior Notes due in 2023 Aggregate principal amount $ 37,099 $ 115,000 Fair value amount 65,440 373,928 0.0 % Convertible Senior Notes due in 2024 Aggregate principal amount $ 690,000 $ 690,000 Fair value amount 656,363 725,100 Note 4 . Property and Equipment, Net Property and equipment, net consisted of the following: January 31, (in thousands) 2022 2021 Computer and network equipment $ 127,799 $ 102,163 Software, including capitalized software development costs 82,537 56,858 Furniture and office equipment 20,939 21,682 Leasehold improvements 79,811 79,892 311,086 260,595 Less: Accumulated depreciation ( 170,261 ) ( 121,029 ) 140,825 139,566 Work in progress 43,839 25,473 $ 184,664 $ 165,039 Depreciation and amortization expenses associated with property and equipment was $ 57.1 million, $ 45.5 million and $ 32.5 million in the years ended January 31, 2022, 2021 and 2020. This included amortization expense related to capitalized internally-developed software costs of $ 10.3 million, $ 6.2 million and $ 4.1 million in the respective years . We capitalized $ 39.0 million, $ 29.3 million and $ 17.1 million of internally developed software costs, including $ 9.8 million, $ 7.2 million and $ 4.1 million of capitalized stock-based compensation in the years ended January 31, 2022, 2021 and 2020. Note 5. Acquisitions Acquisition of Seal Software Group Limited On May 1, 2020, we completed the acquisition of Seal Software Group Limited (“Seal”), a contract analytics and artificial intelligence (“AI”) technology provider headquartered in Walnut Creek, California. The acquisition allows us to integrate Seal's technology comprehensively across the DocuSign Agreement Cloud to deliver increased functionality to companies using the Agreement Cloud to prepare, sign, act on and manage agreements. Under the terms of the purchase agreement, we paid $ 184.7 million in cash, net of cash acquired, transaction costs and working capital adjustments, for Seal’s outstanding stock. Prior to the acquisition, we held a $ 15.0 million minority investment in Seal’s outstanding stock. As of the acquisition, the fair value of our minority interest, calculated as the difference between the total acquisition consideration and the portion attributable to third party Seal shareholders, approximated the carrying value. Additionally, to certain continuing employees of Seal, we granted restricted stock units with service and performance conditions covering up to 0.1 million shares of our common stock with an aggregate grant date fair value of $ 11.4 million that will be accounted for as a post-acquisition compensation expense over the vesting period. The performance-based condition was based on Seal meeting certain bookings targets for the year ended January 31, 2021 and that performance condition was not met. DocuSign, Inc.| 2022 Form 10-K | 81 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 income and cost approaches. Excess purchase price consideration was recorded as goodwill and is primarily attributable to the assembled workforce and expanded market opportunities when integrating Seal’s AI and analytics capabilities within our existing product offering. The following table summarizes the acquisition date fair values of assets acquired and liabilities assumed at the date of acquisition: (in thousands) As Adjusted Cash and cash equivalents $ 729 Accounts receivable 9,654 Contract assets 5,813 Prepaid expense and other assets 4,829 Property and equipment 915 Goodwill 115,848 Intangible assets 83,700 Right-of-use Assets 3,130 Accounts payable ( 854 ) Accrued compensation ( 2,697 ) Contract liabilities ( 7,745 ) Accrued expenses and other liabilities ( 5,852 ) Lease liabilities ( 3,126 ) Deferred tax liability—noncurrent ( 3,891 ) $ 200,453 $ 5.3 million of the goodwill recognized upon acquisition is deductible for U.K. income tax purposes, where Seal is registered. No amount of the goodwill recognized upon acquisition is deductible for U.S. federal income tax purposes. The estimated useful lives of intangible assets, 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 Weighted Average Useful Life Existing technology $ 37,400 5 years Customer relationships—subscription 41,700 10 years Backlog—subscription 4,600 2 years Total intangible assets $ 83,700 7.3 years In the year ended January 31, 2021, we incurred acquisition costs of $ 6.2 million. These costs included legal, accounting fees and other costs directly related to the acquisition of Seal and are recognized within operating expenses in our consolidated statements of operations. In the year ended January 31, 2021, we recognized revenues from Seal of $ 16.3 million and net losses of $ 20.1 million, excluding the impact of acquired intangible asset amortization. The results of operations of Seal were included in our consolidated statements of operations from the acquisition date. The following unaudited pro forma information has been prepared for illustrative purposes only and assumes the acquisition occurred on February 1, 2019. It includes pro forma adjustments related to the amortization of acquired intangible assets, share-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, 2019, or of future results of operations: DocuSign, Inc.| 2022 Form 10-K | 82 Year Ended January 31, (in thousands) (unaudited) 2021 2020 Revenue $ 1,464,424 $ 1,001,809 Net loss ( 246,819 ) ( 262,968 ) Net loss per share attributable to common stockholders, basic and diluted $ ( 1.33 ) $ ( 1.49 ) Acquisition of Liveoak Technologies, Inc. On July 6, 2020, we completed the acquisition of Liveoak Technologies, Inc. (“Liveoak”), a virtual customer engagement and business platform based in Austin, Texas. The company’s platform includes several technologies specific to remote agreements, such as video conferencing, video identity verification, collaborative form-filling, an integration with DocuSign eSignature, and a detailed audit trail. The acquisition enables us to leverage Liveoak’s technology and expertise to accelerate the launch of DocuSign Notary, a new product for remote online notarization, where signers and the notary public are in different places. The consideration to acquire Liveoak’s outstanding stock was $ 48.4 million, which consisted primarily of the fair value of our common stock issued and the fair value of stock options issued to substitute vested Liveoak options. We recorded approximately $ 39.9 million of goodwill which is primarily attributed to the assembled workforce and expanded market opportunities for integrating Liveoak’s technology with our existing product offering. No goodwill recognized upon acquisition was deductible for U.S. federal income tax purposes. In the year ended January 31, 2021, we incurred costs of $ 1.8 million directly related to the acquisition of Liveoak. These costs are recognized within operating expenses in our consolidated statements of operations. We included the results of operations of Liveoak in our consolidated statements of operations from the acquisition date. These results, including pro forma information, were not material to our consolidated statements of operations for the year ended January 31, 2021 . Note 6 . Goodwill and Intangible Assets, Net The changes in the carrying amount of goodwill were as follows (in thousands): Balance at January 31, 2020 $ 194,882 Additions—Seal 114,663 Additions—Liveoak 39,892 Foreign currency translation 714 Balance at January 31, 2021 350,151 Additions—Seal 1,185 Additions—Clause 4,100 Foreign currency translation ( 378 ) Balance at January 31, 2022 $ 355,058 DocuSign, Inc.| 2022 Form 10-K | 83 Intangible assets consisted of the following: As of January 31, 2022 As of January 31, 2021 (in thousands, except years) Weighted-average Remaining Useful Life (Years) Acquisition-related Intangibles, Gross Accumulated Amortization Acquisition-related Intangibles, Net Acquisition-related Intangibles, Gross Accumulated Amortization Acquisition-related Intangibles, Net Existing technology 3.1 $ 76,194 $ ( 47,307 ) $ 28,887 $ 72,994 $ ( 35,613 ) $ 37,381 Customer contracts & related relationships 7.0 110,082 ( 39,911 ) 70,171 110,082 ( 29,393 ) 80,689 Other 0.3 22,534 ( 21,959 ) 575 22,534 ( 19,356 ) 3,178 5.8 $ 208,810 $ ( 109,177 ) 99,633 $ 205,610 $ ( 84,362 ) 121,248 Cumulative translation adjustment ( 817 ) 580 Total $ 98,816 $ 121,828 Amortization of finite-lived intangible assets was as follows: Year Ended January 31, (in thousands) 2022 2021 2020 Cost of subscription revenue $ 11,670 $ 11,052 $ 5,704 Sales and marketing 13,100 14,566 12,013 Total $ 24,770 $ 25,618 $ 17,717 As of January 31, 2022, future amortization of finite-lived intangible assets that will be recorded in cost of revenue and operating expenses is estimated as follows, excluding cumulative translation adjustment: Fiscal Period Amount (in thousands) 2023 $ 20,706 2024 19,375 2025 18,798 2026 12,655 2027 10,518 Thereafter 17,581 Total $ 99,633 DocuSign, Inc.| 2022 Form 10-K | 84 Note 7 . Deferred Contract Acquisition and Fulfillment Costs The following table represents a rollforward of our deferred contract acquisition and fulfillment costs: Year Ended January 31, (in thousands) 2022 2021 Deferred Contract Acquisition Costs Beginning balance $ 262,519 $ 155,697 Additions to deferred contract acquisition costs 169,322 185,970 Amortization of deferred contract acquisition costs ( 112,931 ) ( 81,132 ) Cumulative translation adjustment ( 3,752 ) 1,984 Ending balance $ 315,158 $ 262,519 Deferred Contract Fulfillment Costs Beginning balance $ 12,506 $ 8,218 Additions to deferred contract fulfillment costs 38,071 22,540 Amortization of deferred contract fulfillment costs ( 31,489 ) ( 18,252 ) Ending balance $ 19,088 $ 12,506 Note 8. Debt Convertible Senior Notes In September 2018, we issued $ 575.0 million in aggregate principal amount of the 0.5 % Convertible Senior Notes due in 2023, which included the initial purchasers’ exercise in full of their option to purchase an additional $ 75.0 million aggregate principal amount of the 2023 Notes. The net proceeds from the issuance of the 2023 Notes were $ 560.8 million after deducting the initial purchasers’ discounts and transaction costs. In January 2021, we issued $ 690.0 million in aggregate principal amount of the 0 % Convertible Senior Notes due in 2024, which included the initial purchasers’ exercise in full of their option to purchase an additional $ 90.0 million aggregate principal amount of the 2024 Notes. The net proceeds from the issuance of the 2024 Notes were $ 677.3 million after deducting the initial purchasers’ discounts and transaction costs. The Notes are senior unsecured obligations and rank senior in right of payment to any of our indebtedness that is expressly subordinated in right of payment to the Notes; equal in right of payment to any of our unsecured indebtedness then existing and future liabilities that are not so subordinated; effectively junior in right of payment to any of our secured indebtedness, to the extent of the value of the assets securing such indebtedness; and structurally junior to all indebtedness and other liabilities (including trade payables) of our subsidiaries. Upon conversion of the Notes, holders will receive cash, shares of our common stock or a combination of cash and shares of our common stock, at our election. The 2023 Notes are governed by an indenture dated September 18, 2018 (the “2018 Indenture”). The 2024 Notes are governed by an indenture dated January 15, 2021 (the “2021 Indenture,” and together with the 2018 Indenture, the “Indentures”). The Indentures are between us, as the issuer, and U.S. Bank National Association, as trustee. The Indentures do 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 2023 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 on the 2023 Notes is payable semi-annually in arrears on March 15 and September 15 of each year. The Notes are subject to additional interest in certain events of default. The 2024 Notes mature on January 15, 2024 unless earlier repurchased by us or earlier converted in accordance with their terms prior to the maturity date. DocuSign, Inc.| 2022 Form 10-K | 85 Conversion terms The 2023 Notes have an initial conversion rate of 13.9860 shares of our common stock per $1,000 principal amount of the 2023 Notes, which is equal to an initial conversion price of approximately $ 71.50 per share of our common stock. The 2024 Notes have an initial conversion rate of 2.3796 shares of our common stock per $1,000 principal amount of the 2024 Notes, which is equal to an initial conversion price of approximately $ 420.24 per share of our common stock. The initial conversation rates are subject to adjustment in some events. Following certain corporate events that occur prior to the maturity date or, with respect to the 2023 Notes, 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” as defined within the respective Indentures, 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, if any. No such corporate events have occurred as of January 31, 2022. Holders of the 2023 Notes may convert all or any portion of their 2023 Notes at any time on or after June 15, 2023, until the close of business on September 13, 2023. Prior to the close of business on the business day immediately preceding June 15, 2023, holders of the 2023 Notes may convert all or any portion of their 2023 Notes, in integral multiples of $1,000 principal amount, only under the following circumstances (the “2023 Notes conversion conditions”): • During any fiscal quarter commencing after the fiscal quarter ending on January 31, 2019 (and only during such fiscal quarter), if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding fiscal quarter is greater than or equal to 130 % of the conversion price on each applicable trading day; • During the 5 -business day period after any 10 consecutive trading day period (the “measurement period”) in which the trading price as defined in the 2018 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 2018 Indenture. Based upon the reported sales price of our common stock, the 2023 Notes became convertible on August 1, 2020 and continued to be convertible through January 31, 2022. Holders of the 2024 Notes may convert all or any portion of their 2024 Notes at any time on or after October 15, 2023, until the close of business on September 15, 2024. Prior to the close of business on the business day immediately preceding October 15, 2023, holders of the 2024 Notes may convert all or any portion of their 2024 Notes, in integral multiples of $1,000 principal amount, only under the following circumstances (the “2024 Notes conversion conditions”): • During any fiscal quarter commencing after the fiscal quarter ending on April 30, 2021 (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 2021 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; or • Upon the occurrence of specified corporate events described in the 2021 Indenture. As of January 31, 2022, the 2024 Notes conversion conditions described above were not met and therefore the 2024 Notes are not yet convertible. Redemption terms We may redeem for cash or shares all or any portion of the 2023 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. We may not redeem the 2024 Notes prior to the maturity date. DocuSign, Inc.| 2022 Form 10-K | 86 Repurchases of the 2023 Notes In connection with our issuance of the 2024 Notes in the prior year, we used a portion of the proceeds to repurchase $ 460.0 million aggregate principal amount of the 2023 Notes in privately negotiated transactions for an aggregate consideration of $ 1.7 billion, consisting of $ 459.2 million in cash and 4.7 million shares of our common stock with a value of $ 1.2 billion, a non-cash financing activity. We recorded an extinguishment loss of $ 33.8 million as a result of the transaction. In our consolidated statement of cash flows, the cash paid to repurchase the 2023 Notes was bifurcated into two components: the portion of the repayment attributable to accreted interest related to debt discount is classified as cash outflows from operating activities, and the portion of the repayment attributable to the principal is classified as cash outflows from financing activities. Conversions of the 2023 Notes In January 2021, certain holders of the 2023 Notes exercised their option to convert $ 23.9 million aggregate amount of the principal of the 2023 Notes. As the principal was settled in cash in March 2021, we reclassified $ 20.5 million of the carrying value to “Convertible senior notes—current” and $ 3.4 million, representing the difference between the aggregate principal and the carrying value, to mezzanine equity from permanent equity on our consolidated balance sheet as of January 31, 2021. We accounted for early conversions and settlements of the 2023 Notes during the year ended January 31, 2022 under ASU 2020-06. Refer to Note 1 for further discussion of early adoption. During the year ended January 31, 2022, we settled $ 77.9 million aggregate amount of the principal of 2023 Notes, for aggregate consideration of $ 252.1 million, consisting of $ 77.9 million in cash and 0.7 million shares of our common stock with a value of $ 174.2 million. The $ 0.9 million excess of the cash consideration over the corresponding carrying value was recorded as a reduction to additional paid-in capital. As of January 31, 2022, we had not received conversion notices on our 2023 Notes. DocuSign, Inc.| 2022 Form 10-K | 87 Net Carrying Amounts of the Liability and Equity Components January 31, (in thousands) 2022 2021 2023 Notes (effective interest rate of 5.9 %): Principal $ 575,000 $ 575,000 Less: extinguishment or conversion ( 537,901 ) ( 460,000 ) Unpaid principal 37,099 115,000 Less: unamortized debt discount — ( 15,116 ) Less: unamortized transaction costs ( 303 ) ( 1,224 ) Net carrying value of current and noncurrent liability component $ 36,796 $ 98,660 Proceeds allocated to the conversion option (debt discount) $ 134,667 Less: extinguishment or conversion ( 31,933 ) Less: transaction costs ( 3,336 ) Net carrying value of mezzanine and permanent equity component $ 99,398 Excess of if-converted value over principal $ 28,159 $ 259,578 2024 Notes (effective interest rate of 3.8 %): Principal $ 690,000 $ 690,000 Less: unamortized debt discount — ( 63,619 ) Less: unamortized transaction costs ( 8,309 ) ( 11,353 ) Net carrying value of noncurrent liability component $ 681,691 $ 615,028 Proceeds allocated to the conversion option (debt discount) $ 64,453 Less: transaction costs ( 1,185 ) Net carrying value of permanent equity component $ 63,268 Excess of if-converted value over principal $ — $ — Interest expense recognized related to the Notes was as follows: Year Ended January 31, (in thousands) 2022 2021 2020 Contractual interest expense $ 168 $ 2,773 $ 2,865 Amortization of debt discount — 25,828 24,411 Amortization of transaction costs 4,544 2,173 1,978 Total $ 4,712 $ 30,774 $ 29,254 Capped Calls To minimize the potential economic dilution to our common stock upon conversion of the Notes, we entered into privately-negotiated capped call transactions ("Capped Calls") with certain counterparties. DocuSign, Inc.| 2022 Form 10-K | 88 The capped call transactions were as follows: (in thousands, except per share amounts) 2023 Notes 2024 Notes Aggregate cost of capped calls $ 67,563 $ 31,395 Initial strike price per share (1) $ 71.50 $ 420.24 Initial cap price per share (1) $ 110.00 $ 525.30 Shares of our common stock covered by the capped calls (1) 8,042 1,642 (1) Subject to adjustments for certain events, such as merger events and tender offers, and anti-dilution adjustments Impact on Loss Per Share Upon adoption of ASU 2020-06 on February 1, 2021, in periods when we have net income, the shares of our common stock subject to the Notes outstanding during the period are included in our diluted earnings per share under the if-converted method. Prior to the adoption of ASU 2020-06, had we had net income, the shares of our common stock subject to the Notes outstanding during the period would have been included in our diluted earnings per share. In the fourth quarter of 2021, share settlement was presumed leading to the application of the if-converted method. In periods before that, cash settlement was presumed and shares subject to the Notes would have been included under the treasury stock method. Capped Calls are excluded from the calculation of diluted earnings per share, as they would be antidilutive. However, upon conversion, there will be no economic dilution from the Notes unless the market price of our common stock exceeds the cap prices listed above in the Capped Calls section, as exercise of the Capped Calls offsets any dilution from the Notes from the conversion price up to the cap price. As of January 31, 2022 and January 31, 2021, the market price of our common stock exceeded the $ 110.00 per share cap price associated with the 2023 Notes but not the $ 525.30 cap price associated with the 2024 notes; therefore, the 2023 Notes would have caused economic dilution if converted as of January 31, 2022 and January 31, 2021. Revolving Credit Facility In January 2021, we entered into a credit agreement with a syndicate of banks. The credit agreement extended a senior secured revolving credit facility to us in an aggregate principal amount of $ 500.0 million, which amount may be increased by an additional $ 250.0 million subject to the terms of the credit agreement. We may use the proceeds of future borrowings under the credit facility to finance working capital, capital expenditures and for other general corporate purposes, including permitted acquisitions. The facility matures in January 2026 and requires us to comply with customary affirmative and negative covenants. We were in compliance with all covenants as of January 31, 2022. As of January 31, 2022, there were no outstanding borrowings under the revolving credit facility. The facility is subject to customary fees for loan facilities of this type, including ongoing commitment fees at a rate between 0.25 % and 0.30 % per annum on the daily undrawn balance. Note 9. Leases We lease offices under noncancelable operating lease agreements that expire at various dates through the end of February 2032. As of January 31, 2022, we had no finance leases. Some of our operating leases contain escalation provisions for adjustments in the consumer price index. Operating lease expense for the fiscal years ended January 31, 2022 , 2021 and 2020 was $ 34.4 million, $ 34.0 million and $ 26.5 million. DocuSign, Inc.| 2022 Form 10-K | 89 Future lease payments under noncancelable operating leases as of January 31, 2022, were as follows: Fiscal Period: Amount (in thousands) 2023 $ 43,502 2024 39,699 2025 30,497 2026 19,683 2027 17,491 Thereafter 33,228 Total undiscounted cash flows $ 184,100 Less: imputed interest ( 20,356 ) Present value of lease liabilities $ 163,744 The weighted average remaining lease terms as of January 31, 2022 and 2021 were 5.7 years and 6.6 years. The discount rates for operating leases as of January 31, 2022 and 2021 were both 4.3 %. Note 10 . Commitments and Contingencies As of January 31, 2022, we had unused letters of credit outstanding associated with our various operating leases totaling $ 7.3 million. We have entered into certain noncancelable contractual arrangements that require future purchases of goods and services. These arrangements primarily relate to cloud infrastructure support and sales and marketing activities. As of January 31, 2022, our future noncancelable minimum payments due under these contractual obligations with a remaining term of more than one year were as follows: Fiscal Period: Amount (in thousands) 2023 $ 67,538 2024 52,983 2025 18,553 2026 9,397 2027 2,694 Thereafter 2,016 Total $ 153,181 Indemnification We enter into indemnification provisions under our agreements with customers and other companies in the ordinary course of business, including business partners, contractors and parties performing our research and development. Pursuant to these arrangements, we agree to indemnify and defend the indemnified party for certain claims and related losses suffered or incurred by the indemnified party from actual or threatened third-party claims because of our activities. The duration of these indemnification agreements is generally perpetual. The maximum potential amount of future payments we could be required to make under these indemnification clauses or agreements is not determinable. Historically, we have not incurred material costs to defend lawsuits or settle claims related to these indemnification agreements. As a result, we believe the fair value of these indemnification agreements is not material as of January 31, 2022 and 2021 . 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. DocuSign, Inc.| 2022 Form 10-K | 90 Claims and Litigation From time to time, we may be subject to legal proceedings, claims and litigation made against us in the ordinary course of business. All legal costs associated with litigation are expensed as incurred. We believe the final outcome of these matters, including the case described below, will not have a material adverse effect on our business, consolidated financial position, results of operations or cash flows. DocuSign, Inc. Securities Litigation On February 8, 2022, a putative securities class action was filed in the U.S. District Court for the Northern District of California, captioned Weston v. DocuSign, Inc., et al., Case No. 3:22-cv-00824, naming DocuSign and certain of our current and former officers as defendants. The complaint purports to allege claims under Sections 10(b) and 20(a) of the Securities Exchange Act of 1934, and Rule 10b-5 promulgated thereunder, based on allegedly false and misleading statements about our business and prospects during the course of the COVID-19 pandemic. The suit is purportedly brought on behalf of purchasers of our securities between June 4, 2020 and December 2, 2021. We are not yet required to respond to the complaint, but believe it is devoid of merit. An earlier action alleging similar claims against the same defendants, captioned Collins v. DocuSign, Inc., et al., Case No. 3:22-cv-00851, filed in the Eastern District of New York and subsequently transferred to the Northern District of California, was voluntarily dismissed on February 14, 2022. Note 11. Stockholders' Equity Common Stock Reserved for Future Issuance We have reserved the following shares of common stock, on an as-if converted basis, for future issuance as follows: January 31, (in thousands) 2022 2021 RSUs outstanding 7,993 10,962 Options issued and outstanding 3,105 4,798 Remaining shares available for future issuance under the Equity Incentive Plans 42,199 32,901 Remaining shares available for future issuance under the ESPP 7,993 6,329 Total shares of common stock reserved 61,290 54,990 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 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. 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. 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. Additionally, any shares subject to outstanding awards originally granted under the 2011 Plan that: (i) expire or terminate for any reason prior to exercise or settlement; (ii) are forfeited because of the failure to meet a contingency or condition required to vest such shares or otherwise returned to DocuSign, Inc.; or (iii) are reacquired, withheld (or not issued) to satisfy a tax withholding obligation in connection with an award or to satisfy the purchase price or exercise price of a stock award are added to the reserves of the 2018 Plan. The 2018 Plan permits the granting of incentive stock options, nonstatutory stock options, stock appreciation rights, restricted stock awards, restricted stock unit awards, performance stock awards, performance cash awards and other stock awards. RSUs granted under the 2018 Plan generally vest over a four-year period, either quarterly or with 25 % DocuSign, Inc.| 2022 Form 10-K | 91 vesting at the end of one year and the remainder quarterly thereafter. Additionally, the Company grants performance-based and market-based RSUs to its executives on an annual basis. Shares available for grant under the 2018 Plan for the year ended January 31, 2022 was as follows: (in thousands) Year Ended January 31, 2022 Available at beginning of fiscal year 32,901 Awards authorized 9,641 Shares granted ( 3,391 ) Shares cancelled/expired 1,289 Shares withheld for taxes 1,759 Available at end of fiscal year 42,199 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 9.9 million shares occurre d o n February 1, 2022. RSUs The majority of RSUs granted after January 31, 2018 vest upon the satisfaction of a service-based vesting condition. From time to time, we may also grant RSUs that are subject to either a performance-based or market-based vesting condition. The performance-based conditions will be satisfied upon satisfaction of certain financial performance targets. The market-based conditions will be satisfied if certain milestones based on our common stock price or relative total shareholder return are met. The weighted-average grant date fair value for RSUs granted during the years ended January 31, 2022, 2021 and 2020 was $ 226.20 , $ 144.80 and $ 56.05 per share. The total grant date fair value of RSUs vested during the years ended January 31, 2022, 2021 and 2020 was $ 367.1 million, $ 282.3 million and $ 223.0 million. RSU activity for the year ended January 31, 2022 was as follows: (in thousands, except per share data) Number of Units Weighted-Average Grant Date Fair Value Unvested at January 31, 2021 10,586 $ 83.98 Granted 3,391 226.20 Vested ( 4,845 ) 75.77 Canceled ( 1,289 ) 108.48 Unvested at January 31, 2022 7,843 $ 146.52 As of January 31, 2022, our total unrecognized compensation cost related to RSUs was $ 875.8 million. We expect to recognize this expense over the remaining weighted-average period of approximately 2.2 years. We have $ 55.7 million and $ 46.2 million of unvested RSUs that are subject to market-based vesting conditions as of January 31, 2022 and 2021. We calculated the fair value of the RSU with market conditions using lattice model simulation analysis based on the following assumptions: Year Ended January 31, 2022 2021 2020 Risk-free interest rate 0.30 % 0.22 % 1.87 % Expected dividend yield — % — % — % Expected life (in years) 3.0 3.0 3.0 Expected volatility 46 % 40 % 35 % Weighted-average grant date fair value per share $ 331.26 $ 206.54 $ 45.14 DocuSign, Inc.| 2022 Form 10-K | 92 Stock Options There were no options granted during the years ended January 31, 2022, 2021 and 2020 . Option activity for the year ended January 31, 2022 was as follows: (in thousands, except per share data and years) Number of Options Weighted-Average Exercise Price Per Share Weighted-Average Remaining Contractual Term (Years) Aggregate Intrinsic Value Outstanding at January 31, 2021 4,798 $ 15.55 5.03 $ 1,042,879 Issued as consideration for acquisition — — Exercised ( 1,693 ) 13.97 Canceled/expired — — Outstanding at January 31, 2022, all vested and exercisable 3,105 $ 16.41 4.45 $ 339,286 As of January 31, 2022, there was no remaining unrecognized compensation cost related to stock option grants. The aggregate intrinsic value of options exercised during the years ended January 31, 2022, 2021 and 2020 was $ 391.2 million, $ 302.4 million and $ 325.7 million. The total grant date fair value of options vested during the years ended January 31, 2022, 2021 and 2020 was $ 0.3 million, $ 7.5 million and $ 10.5 million. 2018 Employee Stock Purchase Plan During the year ended January 31, 2019, our board of directors adopted, and our stockholders approved the ESPP. In April 2018, the ESPP went into effect upon the effectiveness of our IPO Registration Statement. The ESPP allows eligible employees to purchase shares of our common stock at a discounted price by accumulating funds, normally through payroll deductions, of up to 15 % of their earnings. The purchase price for common stock under the ESPP is equal to 85 % of the fair market value of our common stock on the first or last day of the offering period, whichever is lower. The ESPP provides for separate six-month offering periods that begin in the first and third quarter of each year. We calculated the fair value of the ESPP purchase right using the Black-Scholes option-pricing model, based on the following assumptions: Year Ended January 31, 2022 2021 2020 Risk-free interest rate 0.04 % - 0.06 % 0.11 % - 0.17 % 1.92 % Expected dividend yield — % — % — % Expected life of purchase right (in years) 0.5 0.5 0.5 Expected volatility 43 % - 58 % 47 % - 58 % 39 % - 52 % Weighted-average grant date fair value per share $ 205.71 - $ 265.12 $ 90.15 - $ 221.20 $ 14.88 - $ 18.56 The expected term for the ESPP purchase rights is based on the duration of the offering period. Estimated volatility for ESPP purchase rights is based on the historical volatility of our common stock price. The interest rate is derived from government bonds with a similar term to the ESPP purchase right granted. We have not declared, nor do we expect to declare dividends. Compensation expense related to the ESPP was $ 18.6 million, $ 12.6 million and $ 8.9 million for the years ended January 31, 2022, 2021 and 2020. The number of shares reserved under the ESPP will automatically increase on the first day of each fiscal year, starting on February 1, 2019 and continuing through February 1, 2028, in an amount equal to the lesser of (i) 1 % of the total number of shares of our common stock outstanding on January 31 of the preceding fiscal year, (ii) 3.8 million shares, or (iii) a lesser number of shares determined by our board of directors. As of January 31, 2022, 8.0 million shares of common stock were reserved for issuance under the ESPP. DocuSign, Inc.| 2022 Form 10-K | 93 Note 12 . Net Loss per Share Attributable to Common Stockholders The following table presents the calculation of basic and diluted net loss per share attributable to common stockholders for periods presented: Year Ended January 31, (in thousands, except per share data) 2022 2021 2020 Numerator: Net loss attributable to common stockholders $ ( 69,976 ) $ ( 243,267 ) $ ( 208,359 ) Denominator: Weighted-average common shares outstanding 196,675 185,760 176,704 Net loss per share attributable to common stockholders: Basic and diluted $ ( 0.36 ) $ ( 1.31 ) $ ( 1.18 ) Outstanding potentially dilutive securities that were excluded from the diluted per share calculations because they would have been antidilutive are as follows: January 31, (in thousands) 2022 2021 2020 RSUs 7,843 10,586 13,555 Stock options 3,105 4,798 6,882 ESPP 287 130 274 Convertible senior notes 2,161 3,250 788 Total antidilutive securities 13,396 18,764 21,499 Note 13. Employee Benefit Plan We have a qualified defined contribution plan under Section 401(k) of the Internal Revenue Code (the “Plan”). This Plan covers substantially all employees who meet minimum age and service requirements and allows participants to defer a portion of their annual compensation on a pre-tax basis. In the fourth quarter of fiscal 2019, we began to match 50 % of each participant’s contribution up to a maximum of 6 % of the participant’s base salary and commissions paid during the period. During the year ended January 31, 2022, 2021 and 2020, we recognized expenses of $ 25.5 million, $ 18.9 million and $ 11.0 million related to matching contributions. Note 14 . Income Taxes The domestic and foreign components of pre-tax loss were as follows: Year Ended January 31, (in thousands) 2022 2021 2020 U.S. $ ( 93,356 ) $ ( 240,175 ) $ ( 228,476 ) International 26,442 10,683 24,920 Loss before income taxes $ ( 66,914 ) $ ( 229,492 ) $ ( 203,556 ) DocuSign, Inc.| 2022 Form 10-K | 94 The components of our income tax provision (benefit) were as follows: Year Ended January 31, (in thousands) 2022 2021 2020 Current Federal $ ( 931 ) $ ( 35 ) $ — State ( 108 ) 269 239 Foreign 3,407 15,951 3,277 Total current 2,368 16,185 3,516 Deferred Federal 213 ( 243 ) — State 184 5 ( 43 ) Foreign 297 ( 2,172 ) 1,330 Total deferred 694 ( 2,410 ) 1,287 Provision for income taxes $ 3,062 $ 13,775 $ 4,803 The reconciliation of the statutory federal income tax rate to our effective tax rate was as follows: Year Ended January 31, (in percentage) 2022 2021 2020 U.S statutory rate 21.0 % 21.0 % 21.0 % State taxes 2.1 2.7 3.5 Foreign tax rate differential ( 3.4 ) 0.1 0.5 Increase (decrease) unrecognized tax benefit 1.0 ( 5.6 ) — Stock-based compensation 309.6 87.1 47.2 Change in valuation allowance ( 386.4 ) ( 118.4 ) ( 80.3 ) Research and development credits 58.2 9.1 8.2 Lapse of Statute of Limitations 1.4 — — Other deferred adjustment ( 9.9 ) ( 1.1 ) — Other 1.8 ( 0.9 ) ( 2.4 ) Effective tax rate ( 4.6 ) % ( 6.0 ) % ( 2.3 ) % DocuSign, Inc.| 2022 Form 10-K | 95 The significant components of net deferred tax balances were as follows: January 31, (in thousands) 2022 2021 Deferred tax assets Net operating loss carryforwards $ 891,414 $ 682,872 Accruals and reserves 15,566 14,744 Stock-based compensation 35,319 30,377 Operating lease liability 29,644 36,148 Research and development credits 99,353 60,386 Other 27,405 14,398 Total deferred tax assets 1,098,701 838,925 Less: Valuation allowance ( 999,191 ) ( 723,767 ) Deferred tax assets, net of valuation allowance 99,510 115,158 Deferred tax liabilities Operating lease right-of-use asset ( 21,038 ) ( 27,654 ) Deferred contract acquisition costs ( 74,727 ) ( 61,432 ) Convertible debt — ( 18,854 ) Acquired intangibles ( 1,006 ) ( 11,939 ) Other ( 9,721 ) ( 893 ) Total deferred tax liabilities ( 106,492 ) ( 120,772 ) Net deferred tax liabilities $ ( 6,982 ) $ ( 5,614 ) We intend to invest substantially all of our foreign subsidiary earnings, as well as our capital in our foreign subsidiaries, indefinitely outside of the U.S. in those jurisdictions in which we would incur significant, additional costs upon repatriation of such amounts. Therefore, no deferred tax liabilities for foreign withholding taxes have been recorded relating to the earnings of our foreign subsidiaries. In the years ended January 31, 2022, 2021 and 2020, total stock-based compensation expense was $ 408.5 million, $ 286.9 million and $ 206.4 million. Recognized tax benefits on total stock-based compensation expense, which are reflected in the "Provision for income taxes" in the consolidated statements of operations and comprehensive loss, were $ 1.6 million, $ 2.2 million and $ 1.0 million in the years ended January 31, 2022, 2021 and 2020. As of January 31, 2022, we had accumulated net operating loss carryforwards of $ 3.7 billion for federal and $ 1.8 billion for state. Of the federal net operating losses, $ 3.2 billion is carried forward indefinitely, but is limited to 80% of taxable income. The remaining federal and state net operating loss carryforwards will begin to expire in 2024 and 2023, respectively. As of January 31, 2022, we also had total foreign net operating loss carryforwards of $ 43.0 million, which do not expire under local law. As of January 31, 2022, we had accumulated U.S. research tax credits of $ 108.5 million for federal and $ 26.8 million for state. The U.S. federal research tax credits will begin to expire in 2033. The U.S. state research tax credits do not expire. Available net operating losses may be subject to annual limitations due to ownership change limitations provided by the Internal Revenue Code, as amended (the "Code"), and similar state provisions. Under Section 382 of the Code, substantial changes in our ownership and the ownership of acquired companies may limit the amount of net operating loss carryforwards that are available to offset taxable income. Our ability to carry forward our federal and state net operating losses is limited due to an ownership change that occurred in a prior fiscal year. This limitation has been accounted for in calculating the available net operating loss carryforwards. The foreign jurisdictions in which we operate may have similar provisions that may limit our ability to use net operating loss carryforwards incurred by entities that we have acquired. Additional limitations on the use of these tax attributes could occur in the event of possible disputes arising in examination from various taxing authorities. DocuSign, Inc.| 2022 Form 10-K | 96 A reconciliation of the beginning and ending balance of total unrecognized tax benefits was as follows: January 31, (in thousands) 2022 2021 Unrecognized tax benefits balance at February 1 $ 33,779 $ 12,885 Gross increase for tax positions of prior years 5,287 2,012 Gross decrease for tax positions of prior years ( 1,513 ) — Gross increase for tax positions of current year 9,176 18,882 Unrecognized tax benefits balance at January 31 $ 46,729 $ 33,779 As of January 31, 2022, the Company had $ 46.7 million of unrecognized tax benefits, of which $ 15.0 million could affect the Company’s effective tax rate, if recognized. The remainder of the unrecognized tax benefits would not affect the effective tax rate due to a significant portion of the unrecognized tax benefit being recorded as a reduction in our gross deferred tax asset, offset by a reduction in our valuation allowance. A significant portion of the unrecognized tax benefit was recorded as a reduction in our gross deferred tax assets, offset by a reduction in our valuation allowance. We have net uncertain tax positions of $ 16.2 million, $ 16.7 million and $ 3.3 million included in other liabilities on our consolidated balance sheet as of January 31, 2022, 2021 and 2020. We do not expect our gross unrecognized tax benefit to change significantly within the next 12 months. We recognize interest and penalties related to uncertain tax positions in provision for income taxes. As of January 31, 2022, accrued interest and penalties was $ 1.3 million. Our tax years from inception in 2003 through January 31, 2022, remain subject to examination by the U.S. and California, as well as various other jurisdictions. We are under examination by the Israeli Tax Authorities for the period January 1, 2016 through January 31, 2021. The Company believes that it has reserved adequate amounts for these jurisdictions. We recognize valuation allowances on deferred tax assets if it is more likely than not that some or all the deferred tax assets will not be realized. Due to our history of losses in the U.S., the net cumulative U.S. deferred tax assets have been fully offset by a valuation allowance. The valuation allowance increased by $ 275.4 million in the year ended January 31, 2022 and by $ 278.0 million in the year ended January 31, 2021. The following table represents the rollforward of our valuation allowance: Year Ended January 31, (in thousands) 2022 2021 2020 Beginning balance $ 723,767 $ 445,746 $ 282,141 Valuation allowance charged to income tax provision 256,017 269,135 163,605 Valuation allowance from acquisitions — 9,354 — Convertible senior notes settled — 14,985 — Convertible senior notes issued — ( 15,453 ) — Adoption of ASU 2020-06 19,407 — — Ending balance $ 999,191 $ 723,767 $ 445,746 DocuSign, Inc.| 2022 Form 10-K | 97 Note 15 . Geographic Information We operate in one operating segment and one reportable segment as we only report financial information on an aggregate and consolidated basis to the Chief Executive Officer, who is our CODM. Revenue by geography is based on the address of the customer as specified in our master subscription agreement. Revenue by geographic area was as follows: Year Ended January 31, (in thousands) 2022 2021 2020 U.S. $ 1,625,966 $ 1,166,004 $ 802,480 International 481,247 287,043 171,491 Total revenue $ 2,107,213 $ 1,453,047 $ 973,971 No single country other than the U.S. had revenue greater than 10% of total revenue in the years ended January 31, 2022, 2021 and 2020. Our long-lived assets by geographic area, which consist of property and equipment, net and operating lease right-of-use assets were as follows: January 31, (in thousands) 2022 2021 U.S. $ 218,048 $ 221,549 Ireland 55,061 66,670 All other countries 37,576 36,172 Total long-lived assets $ 310,685 $ 324,391 Note 16 . Subsequent Events In March 2022, our Board of Directors authorized a stock repurchase program of up to $ 200 million of our outstanding common stock. The program has no minimum purchase commitment and no mandated end date. The repurchase program may be suspended or discontinued at any time at our discretion. The timing and the amount of any repurchased common stock will be determined by management based on its evaluation of market conditions and other factors. ITEM 9. CHANGES IN AND DISAGREEMENTS WITH ACCOUNTANTS ON ACCOUNTING AND FINANCIAL DISCLOSURE None.