APPIAN CORP 10-K

Item 8. Financial Statements and Supplementary Data INDEX TO CONSOLIDATED FINANCIAL STATEMENTS Consolidated Financial Statements: Page Report of Independent Registered Public Accounting Firm ( BDO USA, LLP ; McLean, Virginia ; PCAOB ID # 243 ) 60 Consolidated Balance Sheets 64 Consolidated Statements of Operations 65 Consolidated Statements of Comprehensive Loss 66 Consolidated Statements of Changes in Stockholders' Equity 67 Consolidated Statements of Cash Flows 68 Notes to Consolidated Financial Statements 69 59 Report of Independent Registered Public Accounting Firm Shareholders and Board of Directors Appian Corporation McLean, Virginia Opinion on the Consolidated Financial Statements We have audited the accompanying consolidated balance sheets of Appian Corporation (the “Company”) as of December 31, 2022 and 2021, the related consolidated statements of operations, comprehensive loss, changes in stockholders’ equity, and cash flows for each of the three years in the period ended December 31, 2022, and the related notes (collectively referred to as the “consolidated financial statements”). In our opinion, the consolidated financial statements present fairly, in all material respects, the financial position of the Company at December 31, 2022 and 2021, and the results of its operations and its cash flows for each of the three years in the period ended December 31, 2022, in conformity with accounting principles generally accepted in the United States of America. We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (“PCAOB”), the Company's internal control over financial reporting as of December 31, 2022, based on criteria established in Internal Control – Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (“COSO”) and our report dated February 16, 2023 expressed an unqualified opinion thereon. Basis for Opinion These consolidated financial statements are the responsibility of the Company’s management. Our responsibility is to express an opinion on the Company’s consolidated financial statements based on our audits. We are a public accounting firm registered with the 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 audit to obtain reasonable assurance about whether the consolidated financial statements are free of material misstatement, whether due to error or fraud. Our audits 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. We believe that our audits provide a reasonable basis for our opinion. Critical Audit Matter 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: (1) relates to accounts or disclosures that are material to the consolidated financial statements and (2) involved our especially challenging, subjective, or complex judgments. The communication of the critical audit matter 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 for Multiple Performance Obligations As discussed in Note 3 to the consolidated financial statements, certain of the Company's revenue contracts contain multiple performance obligations that might include cloud subscriptions, term license subscriptions, maintenance and support and professional services. The Company accounts for individual products and services separately if they are capable of being distinct and are distinct within the context of the contract. In such cases, the transaction price is allocated to the distinct performance obligations based on their relative standalone selling price or residual approach and revenue is recognized when control of the distinct performance obligation is transferred. 60 We identified the identification of distinct performance obligations and the determination of standalone selling prices as a critical audit matter. Auditing these elements of revenue recognition was especially challenging due to the significant judgment involved in assessing the completeness of the distinct performance obligations in arrangements containing multiple performance obligations. In addition, the evaluation of the reasonableness of the range of prices used to establish the standalone selling price for maintenance and support and professional services was complex, which directly affects the amount of cloud and term license subscriptions revenue recognized using the residual approach. The primary procedures we performed to address this critical audit matter included: • Testing the design and operating effectiveness of internal controls over the Company's revenue recognition process including controls over: (i) the identification of distinct performance obligations, and (ii) the determination of standalone selling prices for the distinct performance obligations. • Testing a sample of revenue contracts and underlying order documents to evaluate management’s identification of distinct performance obligations. • Evaluating the reasonableness of management’s analysis supporting the standalone selling prices by tracing, on a sample basis, revenue transactions to the underlying source documents and recalculating the mathematical accuracy of the analysis. /s/ BDO USA, LLP We have served as the Company's auditor since 2013. McLean, Virginia February 16, 2023 61 Report of Independent Registered Public Accounting Firm Shareholders and Board of Directors Appian Corporation McLean, Virginia Opinion on Internal Control over Financial Reporting We have audited Appian Corporation’s (the “Company’s”) internal control over financial reporting as of December 31, 2022, based on criteria established in Internal Control – Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (the “COSO criteria”). In our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of December 31, 2022, based on the COSO criteria . We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (“PCAOB”), the consolidated balance sheets of the Company as of December 31, 2022 and 2021, the related consolidated statements of operations, comprehensive loss, changes in stockholders’ equity, and cash flows for each of the three years in the period ended December 31, 2022, and the related notes and our report dated February 16, 2023 expressed an unqualified opinion thereon. Basis for Opinion The Company’s management is responsible for maintaining effective internal control over financial reporting and for its assessment of the effectiveness of internal control over financial reporting, included in the accompanying Item 9A, Management’s Annual Report on Internal Control over Financial Reporting. Our responsibility is to express an opinion on the Company’s internal control over financial reporting based on our audit. We are a public accounting firm registered with the PCAOB and are required to be independent with respect to the Company in accordance with U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB. We conducted our audit of internal control over financial reporting in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audit to obtain reasonable assurance about whether effective internal control over financial reporting was maintained in all material respects. Our audit 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 audit also included performing such other procedures as we considered necessary in the circumstances. We believe that our audit provides a reasonable basis for our opinion. 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 (1) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the transactions and dispositions of the assets of the company; (2) 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 (3) provide reasonable assurance regarding prevention or timely 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. /s/ BDO USA, LLP 62 McLean, Virginia February 16, 2023 63 APPIAN CORPORATION AND SUBSIDIARIES CONSOLIDATED BALANCE SHEETS (in thousands, except share and per share data) As of December 31, 2022 2021 Assets Current assets Cash and cash equivalents $ 148,132 $ 100,796 Short-term investments and marketable securities 47,863 55,179 Accounts receivable, net of allowance of $ 2,125 and $ 1,400 , respectively 165,964 130,049 Deferred commissions, current 30,196 24,668 Prepaid expenses and other current assets 28,093 26,781 Restricted cash, current 2,249 791 Total current assets 422,497 338,264 Property and equipment, net of accumulated depreciation of $ 18,864 and $ 14,106 , respectively 41,855 36,913 Long-term investments — 12,044 Goodwill 26,349 27,795 Intangible assets, net of accumulated amortization of $ 2,715 and $ 1,260 , respectively 5,251 7,144 Operating right-of-use assets 37,248 27,897 Deferred commissions, net of current portion 55,788 49,017 Deferred tax assets 1,940 1,025 Restricted cash, net of current portion — 2,373 Other assets 3,286 2,047 Total assets $ 594,214 $ 504,519 Liabilities and Stockholders’ Equity Current liabilities Accounts payable $ 7,997 $ 5,766 Accrued expenses 12,227 15,483 Accrued compensation and related benefits 40,718 35,126 Deferred revenue, current 194,768 150,169 Debt, current 2,740 — Operating lease liabilities, current 8,681 8,110 Other current liabilities 3,121 1,067 Total current liabilities 270,252 215,721 Long-term debt 115,379 — Operating lease liabilities 57,225 48,784 Deferred revenue 5,556 2,430 Deferred tax liabilities 102 209 Other non-current liabilities — 3,458 Total liabilities 448,514 270,602 Commitments and contingent liabilities (see Note 4 and Note 14) Stockholders’ equity Class A common stock—par value $ 0.0001 ; 500,000,000 shares authorized and 41,320,091 shares issued and outstanding as of December 31, 2022; 500,000,000 shares authorized and 39,964,298 shares issued and outstanding as of December 31, 2021 4 4 Class B common stock—par value $ 0.0001 ; 100,000,000 shares authorized and 31,497,796 shares issued and outstanding as of December 31, 2022; 100,000,000 shares authorized and 31,497,796 shares issued and outstanding as of December 31, 2021 3 3 Additional paid-in capital 561,390 497,128 Accumulated other comprehensive loss ( 7,246 ) ( 5,687 ) Accumulated deficit ( 408,451 ) ( 257,531 ) Total stockholders’ equity 145,700 233,917 Total liabilities and stockholders’ equity $ 594,214 $ 504,519 The accompanying notes are an integral part of these consolidated financial statements. 64 APPIAN CORPORATION AND SUBSIDIARIES CONSOLIDATED STATEMENTS OF OPERATIONS (in thousands, except share and per share data) Year Ended December 31, 2022 2021 2020 Revenue Subscriptions $ 340,152 $ 263,738 $ 198,710 Professional services 127,839 105,521 105,863 Total revenue 467,991 369,259 304,573 Cost of revenue Subscriptions 36,005 27,330 20,826 Professional services 97,301 76,763 67,940 Total cost of revenue 133,306 104,093 88,766 Gross profit 334,685 265,166 215,807 Operating expenses Sales and marketing 220,374 167,852 130,316 Research and development 139,210 97,517 70,241 General and administrative 120,111 83,704 53,152 Total operating expenses 479,695 349,073 253,709 Operating loss ( 145,010 ) ( 83,907 ) ( 37,902 ) Other non-operating expense (income) Other expense (income), net 3,545 3,584 ( 5,786 ) Interest expense 1,673 372 478 Total other non-operating expense (income) 5,218 3,956 ( 5,308 ) Loss before income taxes ( 150,228 ) ( 87,863 ) ( 32,594 ) Income tax expense 692 778 883 Net loss $ ( 150,920 ) $ ( 88,641 ) $ ( 33,477 ) Net loss per share: Basic and diluted $ ( 2.08 ) $ ( 1.25 ) $ ( 0.48 ) Weighted average common shares outstanding: Basic and diluted 72,455,175 71,036,490 69,050,565 The accompanying notes are an integral part of these consolidated financial statements. 65 APPIAN CORPORATION AND SUBSIDIARIES CONSOLIDATED STATEMENTS OF COMPREHENSIVE LOSS (in thousands) Year Ended December 31, 2022 2021 2020 Net loss $ ( 150,920 ) $ ( 88,641 ) $ ( 33,477 ) Comprehensive loss, net of income taxes Foreign currency translation adjustments ( 1,559 ) ( 677 ) ( 4,703 ) Unrealized losses on available-for-sale securities — — ( 22 ) Total other comprehensive loss, net of income taxes $ ( 152,479 ) $ ( 89,318 ) $ ( 38,202 ) The accompanying notes are an integral part of these consolidated financial statements. 66 APPIAN CORPORATION AND SUBSIDIARIES CONSOLIDATED STATEMENTS OF CHANGES IN STOCKHOLDERS' EQUITY (in thousands, except share data) Common Stock Additional Paid-In Capital Accumulated Other Comprehensive Loss Accumulated Deficit Total Stockholders' Equity Shares Amount Balance December 31, 2019 67,468,022 $ 6 $ 340,929 $ ( 285 ) $ ( 135,413 ) $ 205,237 Net loss — — — — ( 33,477 ) ( 33,477 ) Issuance of common stock from public offering, net of issuance costs 1,931,206 1 107,914 — — 107,915 Issuance of common stock to directors 7,942 — — — — — Vesting of restricted stock units 270,609 — — — — — Exercise of stock options 1,001,411 — 6,376 — — 6,376 Stock-based compensation expense — — 15,279 — — 15,279 Other comprehensive loss — — — ( 4,725 ) — ( 4,725 ) Balance December 31, 2020 70,679,190 7 470,498 ( 5,010 ) ( 168,890 ) 296,605 Net loss — — — — ( 88,641 ) ( 88,641 ) Issuance of common stock to directors 4,950 — — — — — Vesting of restricted stock units 354,130 — — — — — Exercise of stock options 423,824 — 2,786 — — 2,786 Stock-based compensation expense — — 23,844 — — 23,844 Other comprehensive loss — — — ( 677 ) — ( 677 ) Balance December 31, 2021 71,462,094 7 497,128 ( 5,687 ) ( 257,531 ) 233,917 Net loss — — — — ( 150,920 ) ( 150,920 ) Issuance of common stock to directors 14,928 — — — — — Vesting of restricted stock units 403,648 — — — — — Exercise of stock options 937,217 — 25,432 — — 25,432 Stock-based compensation expense — — 38,830 — — 38,830 Other comprehensive loss — — — ( 1,559 ) — ( 1,559 ) Balance December 31, 2022 72,817,887 $ 7 $ 561,390 $ ( 7,246 ) $ ( 408,451 ) $ 145,700 The accompanying notes are an integral part of these consolidated financial statements. 67 APPIAN CORPORATION AND SUBSIDIARIES CONSOLIDATED STATEMENTS OF CASH FLOWS (in thousands) Year Ended December 31, 2022 2021 2020 Cash flows from operating activities: Net loss $ ( 150,920 ) $ ( 88,641 ) $ ( 33,477 ) Adjustments to reconcile net loss to net cash used by operating activities: Stock-based compensation 38,830 23,844 15,279 Depreciation and amortization of intangible assets 7,297 5,743 5,851 Bad debt expense 1,298 410 984 Amortization of debt issuance costs 43 — — Loss on disposal of property and equipment 3 79 22 Change in fair value of available-for-sale securities — — 22 Deferred income taxes ( 1,089 ) ( 498 ) ( 184 ) Changes in assets and liabilities: Accounts receivable ( 37,922 ) ( 33,904 ) ( 33,559 ) Prepaid expenses and other assets ( 2,027 ) 2,094 3,740 Deferred commissions ( 12,298 ) ( 21,588 ) ( 8,575 ) Accounts payable and accrued expenses ( 3,289 ) 11,467 ( 4,238 ) Accrued compensation and related benefits 6,582 12,598 11,801 Other current and non-current liabilities ( 264 ) ( 444 ) 3,681 Deferred revenue 47,534 33,378 27,626 Operating lease assets and liabilities ( 329 ) 1,544 3,407 Net cash used by operating activities ( 106,551 ) ( 53,918 ) ( 7,620 ) Cash flows from investing activities: Proceeds from investments 84,642 120,593 — Purchases of investments ( 65,283 ) ( 41,870 ) ( 145,968 ) Purchases of property and equipment ( 9,095 ) ( 6,058 ) ( 1,251 ) Payments for acquisitions, net of cash acquired — ( 30,729 ) ( 6,138 ) Net cash provided by (used by) investing activities 10,264 41,936 ( 153,357 ) Cash flows from financing activities: Proceeds from borrowings 120,000 — — Payments for debt issuance costs ( 1,940 ) — — Debt repayments ( 625 ) — — Proceeds from exercise of common stock options 25,432 2,786 6,376 Proceeds from public offerings, net of underwriting discounts — — 108,260 Payments of costs related to public offerings — — ( 346 ) Principal payments on finance leases — — ( 3,822 ) Net cash provided by financing activities 142,867 2,786 110,468 Effect of foreign exchange rate changes on cash, cash equivalents, and restricted cash ( 159 ) 694 3,216 Net increase (decrease) in cash, cash equivalents, and restricted cash 46,421 ( 8,502 ) ( 47,293 ) Cash, cash equivalents, and restricted cash at beginning of period 103,960 112,462 159,755 Cash, cash equivalents, and restricted cash at end of period $ 150,381 $ 103,960 $ 112,462 Supplemental cash flow information: Cash paid for interest $ 1,671 $ 323 $ 165 Cash paid for income taxes $ 1,239 $ 1,505 $ 1,182 Supplemental non-cash investing and financing information: Accrued capital expenditures $ 1,774 $ 379 $ — The accompanying notes are an integral part of these consolidated financial statements. 68 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 1. Organization and Description of Business Appian Corporation (together with its subsidiaries, “Appian,” the “Company,” “we,” or “our”) is a software company that automates business processes. The Appian Platform includes everything you need to design, automate, and optimize even the most complex processes, from start to finish. The world's most innovative organizations trust Appian to improve their workflows, unify data, and optimize operations—resulting in better growth and superior customer experiences. We are headquartered in McLean, Virginia and operate both in the U.S. and internationally including Australia, Canada, France, Germany, India, Italy, Japan, Mexico, the Netherlands, Singapore, Spain, Sweden, Switzerland, and the United Kingdom. 2. Accounting Policies Basis of Presentation The accompanying consolidated financial statements and footnotes have been prepared in accordance with accounting principles generally accepted in the United States (“U.S. GAAP”) as contained in the Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”). Use of Estimates The preparation of our consolidated financial statements in conformity with U.S. GAAP requires us to make estimates and judgments that affect the amounts reported in these consolidated financial statements and accompanying notes. Although we believe the estimates we use are reasonable, due to the inherent uncertainty involved in making these estimates, actual results reported in future periods could differ from those estimates. Significant estimates embedded in the consolidated financial statements include, but are not limited to, revenue recognition, income taxes and the related valuation allowance, costs to obtain a contract with a customer, and stock-based compensation. Principles of Consolidation The accompanying consolidated financial statements include the accounts of Appian and its wholly-owned subsidiaries. All intercompany accounts and transactions have been eliminated in consolidation. Segment Reporting Operating segments are defined as components of an enterprise for which discrete financial information is available that is evaluated regularly by the chief operating decision maker (“CODM”) for purposes of allocating resources and evaluating financial performance. We have determined our CODM is our Chief Executive Officer. We operate one operating and reportable segment, representing our consolidated business that helps organizations build applications and workflows rapidly with our low-code platform to maximize their resources and improve business results. Our reportable segment determination is based on our management and internal reporting structure, the nature of the subscriptions and services we offer, and the financial information evaluated regularly by our CODM. Revenue Recognition Refer to Note 3 for a detailed discussion on specific revenue recognition principles related to our major revenue streams. 69 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Concentration of Credit and Customer Risk Our financial instruments exposed to concentration of credit and customer risk consist primarily of cash, cash equivalents, restricted cash, accounts receivable, and our short- and long-term investments. Deposits held with banks may exceed the amount of insurance provided on such deposits; however, we believe the financial institutions holding our cash deposits are financially sound and, accordingly, minimal credit risk exists with respect to these balances. With regard to our customers, credit evaluation and account monitoring procedures are used to minimize the risk of loss. Revenue generated from government agencies represented 19.2 %, 19.6 %, and 18.1 % of our revenue for the years ended December 31, 2022, 2021, and 2020, respectively, of which the top three U.S. federal government agencies generated 4.5 %, 5.6 %, and 6.6 % of our revenue for the years ended December 31, 2022, 2021, and 2020, respectively. Additionally, 33.5 %, 34.0 %, and 33.8 % of our revenue during the years ended December 31, 2022, 2021, and 2020, respectively, was generated from international customers. Cash, Cash Equivalents, and Restricted Cash We consider all highly liquid investments with original maturities of three months or less at the date of purchase, as well as overnight repurchase agreements, to be cash equivalents. Restricted cash consists of cash designated to settle an escrow liability stemming from our acquisition of Lana Labs GmbH (“Lana Labs”). The remaining balance as of December 31, 2022 is due on August 11, 2023. The following table presents a reconciliation of cash, cash equivalents, and restricted cash as presented in the consolidated statements of cash flows (in thousands): Year Ended December 31, 2022 2021 2020 Cash and cash equivalents $ 148,132 $ 100,796 $ 112,462 Restricted cash, current 2,249 791 — Restricted cash, non-current — 2,373 — Total cash, cash equivalents, and restricted cash $ 150,381 $ 103,960 $ 112,462 Accounts Receivable and Allowance for Doubtful Accounts Accounts receivable are stated at realizable value, net of an allowance for doubtful accounts. The allowance for doubtful accounts is based on our assessment of the collectability of accounts and incorporates an estimation of expected lifetime credit losses on our receivables. We regularly review the composition of the accounts receivable aging, historical bad debts, changes in payment patterns, customer creditworthiness, and current economic trends. If the financial condition of our customers were to deteriorate, resulting in their inability to make required payments, additional provisions for doubtful accounts would be required and would increase bad debt expense. Activity in the allowance for doubtful accounts was as follows (in thousands): Year Ended December 31, 2022 2021 2020 Beginning balance $ 1,400 $ 1,400 $ 600 Additions 1,298 410 984 Less: Write-offs, net of recoveries ( 573 ) ( 410 ) ( 184 ) Ending balance $ 2,125 $ 1,400 $ 1,400 70 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Assets Recognized from the Costs to Obtain a Contract with a Customer We capitalize incremental costs of obtaining a contract with a customer, which consists of sales commissions paid to our sales team. These costs are recorded as deferred commissions in the consolidated balance sheets. Costs to obtain a contract for a new customer or upsell are amortized over an estimated economic life of five years as sales commissions on initial sales are not commensurate with sales commissions on contract renewals. We determine the estimated economic life based on both qualitative and quantitative factors such as customer attrition, expected renewals, product life cycles, and contractual terms. We periodically review the carrying amount of deferred contract acquisition costs to determine whether events or changes in circumstances have occurred that could impact the estimated economic life. Commissions paid relating to contract renewals are deferred and amortized over the related renewal period. Costs to obtain a contract for professional services arrangements are expensed as incurred as the contractual period of our professional services arrangements are one year or less. Amortization associated with deferred commissions is recorded to sales and marketing expense in our consolidated statements of operations. The following table summarizes the activity of costs to obtain a contract with a customer for the years ended December 31, 2022, and 2021 (in thousands): Year Ended December 31, 2022 2021 Beginning balance $ 73,685 $ 52,097 Additional contract costs deferred 49,816 51,283 Amortization of deferred contract costs ( 37,517 ) ( 29,695 ) Ending balance $ 85,984 $ 73,685 Commission expense was $ 39.4 million, $ 32.4 million, and $ 23.3 million for the years ended December 31, 2022, 2021, and 2020, respectively. Property and Equipment Property and equipment are stated at cost less accumulated depreciation. Depreciation is computed using the straight-line method over the estimated useful lives of the assets. Significant additions or improvements extending the useful life of an asset are capitalized, while repairs and maintenance costs which do not significantly improve the related assets or extend their useful lives are charged to expense as incurred. The following table outlines the useful lives of our major asset categories: Asset Category Useful Life (in years) Computer software 3 Computer hardware 3 Equipment 5 Office furniture and fixtures 10 Leasehold improvements (a) (a) - Leasehold improvements have an estimated useful life of the shorter of the useful life of the assets or the lease term. Business Combinations We account for business combinations using the acquisition method of accounting as of the business combination date. Under this method, we allocate the fair value of purchase consideration to identifiable tangible and intangible assets acquired and liabilities assumed at their estimated fair values on the acquisition date. The excess of the consideration transferred over the fair value of the identifiable net assets acquired is recorded as goodwill and represents the future economic benefits expected to arise from other intangible assets acquired that do not qualify for separate recognition, including assembled workforce, non-contractual relationships, and expected future synergies. Determining the fair value of assets acquired and liabilities assumed requires us to use significant judgments and estimates, including the selection of valuation methodologies, estimates of future revenue, costs, and cash flows, and discount rates. 71 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS During the measurement period, which can be up to one year from the acquisition date, these estimates may be refined, as necessary, and we may record adjustments to the fair value of tangible and intangible assets acquired and liabilities assumed, with the corresponding offset to goodwill. Upon the conclusion of the measurement period or the final determination of the fair value of assets acquired or liabilities assumed, whichever comes first, any subsequent adjustments are recorded to our consolidated statements of operations. Acquisition related expenses and post-acquisition integration costs are recognized separately from the business combination and are expensed as incurred. Impairment of Long-Lived Assets Long-lived tangible assets and intangible assets with definite useful lives are reviewed for impairment whenever events or changes in circumstances indicate the carrying amount of an asset may not be recoverable through undiscounted cash flows from the use of the assets. If such assets are considered to be impaired, the assets are written down to their estimated fair value. Goodwill is accounted for at the segment level and allocated to, and tested for impairment at, a level referred to as the reporting unit. We have determined our one segment consists of a single reporting unit. We test for impairment annually on the first day of our fourth quarter or between annual tests if events or changes in circumstances indicate the fair value of our reporting unit may be below its carrying amount. We have the option to qualitatively assess whether it is more likely than not the fair value our reporting unit is less than its carrying value. If we elect to perform a qualitative assessment and conclude it is more likely than not the fair value of the reporting unit is equal to or greater than its carrying value, no further assessment of that reporting unit’s goodwill is necessary; otherwise, goodwill must be tested for impairment. In 2022, we elected to not perform the optional qualitative assessment of goodwill and instead performed the quantitative impairment test. When performing the quantitative test, we determine the fair value of the reporting unit and compare it to the carrying amount, including goodwill. If the carrying amount of the reporting unit exceeds the fair value of the reporting unit, the reporting unit’s goodwill is impaired, and we must recognize an impairment loss for the difference between the carrying amount and the fair value of the reporting unit. We estimate the fair value of our reporting unit using a market-based valuation methodology, which is primarily based on our consolidated market capitalization plus a reasonable control premium. In the fourth quarter of 2022, we completed our annual goodwill impairment test for our reporting unit, and the results of the test indicated the estimated fair value of our reporting unit significantly exceeded the carrying value. Investments and Fair Value of Financial Instruments Refer to Note 17 for a detailed discussion on our policies specific to investments and determining fair value. Stock-Based Compensation We account for stock-based compensation expense related to stock-based awards based on the estimated fair value of the award on the grant date. We calculate the fair value of stock options containing only a service condition using the Black-Scholes option pricing model. The fair value of restricted stock units (“RSUs”) is based on the closing market price of our common stock on the Nasdaq Global Market on the date of grant. For service-based awards such as RSUs, stock-based compensation expense is recognized on a straight-line basis over the requisite service period. For awards that contain market conditions, compensation expense is measured using a Monte Carlo simulation and is recognized using the accelerated attribution method over the derived service period based on the expected market performance as of the grant date. We account for forfeitures as they occur rather than estimating expected forfeitures. Refer to Note 11 for additional information related to stock-based compensation. Leases We combine and account for lease and non-lease components as a single lease component for leases of our facilities. The discount rates related to the our lease liabilities are based on estimates of our incremental borrowing rate on a secured basis, as the discount rates implicit in our lease agreements cannot be readily determined. 72 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Basic and Diluted Loss per Common Share We compute net loss per common share using the two-class method required for multiple classes of common stock and participating securities. The rights, including the liquidation and dividend rights, of the Class A common stock and Class B common stock are substantially identical, other than voting and conversion rights. Accordingly, the Class A common stock and Class B common stock share equally in our net losses. Basic net loss per common share is computed by dividing net loss by the weighted-average number of shares of common stock outstanding during the period. Diluted net loss per common share is computed by dividing net loss attributable to common stockholders by the weighted-average number of shares of common stock outstanding during the period increased by common shares that could be issued upon the conversion or exercise of other outstanding securities to the extent those additional common shares would be dilutive. The dilutive effect of potentially dilutive securities is reflected in diluted net loss per share by application of the treasury stock method. Income Taxes We use the asset and liability method of accounting for income taxes in which deferred tax assets and liabilities are recognized for the future tax consequences attributable to differences between the consolidated financial statement carrying amounts of existing assets and liabilities and their respective tax bases. We measure deferred tax assets and liabilities using enacted tax rates expected to apply to taxable income in the years in which those temporary differences are expected to be recoverable or settled. We recognize the effect on deferred tax assets and liabilities of a change in tax rates as income and expense in the period that includes the enactment date. A valuation allowance is established if it is more likely than not that all or a portion of the deferred tax asset will not be realized. Our tax positions are subject to income tax audits by multiple tax jurisdictions throughout the world. We recognize the tax benefit of an uncertain tax position only if it is more likely than not the position is sustainable upon examination by the taxing authority. We measure the tax benefit recognized as the largest amount of benefit which is more likely than not to be realized upon settlement with the taxing authority. We recognize penalties and interest related to unrecognized tax benefits as income tax expense. We calculate the current and deferred income tax provision based on estimates and assumptions that could differ from the actual results reflected in income tax returns filed in subsequent years and record adjustments based on filed income tax returns when identified. The amount of income taxes paid is subject to examination by U.S. federal, state, and foreign tax authorities. The estimate of the potential outcome of any uncertain tax issue is subject to our assessment of relevant risks, facts, and circumstances existing at that time. To the extent the assessment of such tax position changes, we record the change in estimate in the period in which we make that determination. Foreign Currency Our operations located outside of the United States where the local currency is the functional currency are translated into U.S. dollars using the current rate method. Results of operations are translated at the average rate of exchange for the period. Assets and liabilities are translated at the closing rates on the balance sheet date. Gains and losses on translation of these accounts are accumulated and reported as a separate component of stockholders’ equity and other comprehensive loss. Gains and losses on foreign currency transactions are recognized in the accompanying consolidated statements of operations as a component of Other expense (income), net. Gains and losses from transactions denominated in foreign currencies resulted in net transaction losses of $ 6.1 million, net transaction losses of $ 3.7 million, and net transaction gains of $ 4.3 million for the years ended December 31, 2022, 2021, and 2020, respectively. Research and Development Research and development expenses include payroll, employee benefits, and other headcount-related costs associated with product development. Our product utilizes a common codebase, whether accessed by customers via the cloud or via an on-premises installation. Since our software is sold and licensed externally, we consider our software as external-use software for purposes of applying the capitalized software development guidance. Product development costs are expensed as incurred until 73 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS technological feasibility has been established, which is defined as the completion of all planning, designing, coding, and testing activities necessary to establish products that meet design specifications including functions, features, and technical performance requirements. We have determined technological feasibility for our software products is reached shortly before they are released for sale. Costs incurred after technological feasibility is established are not significant, and accordingly we expense all research and development costs when incurred. Advertising Expenses We expense advertising costs as they are incurred. Advertising expenses were $ 5.8 million, $ 4.4 million, and $ 6.0 million for the years ended December 31, 2022, 2021, and 2020, respectively. Recent Accounting Pronouncements We did not adopt any new accounting guidance in 2022 that had a material impact on our consolidated financial statements or disclosures. Additionally, there is no pending accounting guidance that we expect to have a material impact on our consolidated financial statements. 3. Revenue Revenue Recognition We generate subscriptions revenue primarily through the sale of cloud subscriptions bundled with maintenance and support and hosting services as well as term license subscriptions bundled with maintenance and support. We generate professional services revenue from fees for our consulting services, including application development and deployment assistance as well as training related to our platform. The following table summarizes revenue recorded during the years ended December 31, 2022, 2021, and 2020 (in thousands): Year Ended December 31, 2022 2021 2020 Cloud subscriptions $ 236,922 $ 179,415 $ 129,219 Term license subscriptions 79,753 63,203 51,415 Maintenance and support 23,477 21,120 18,076 Total subscriptions 340,152 263,738 198,710 Professional services 127,839 105,521 105,863 Total revenue $ 467,991 $ 369,259 $ 304,573 Performance Obligations and Timing of Revenue Recognition We primarily sell products and services that fall into the categories discussed below. Each category contains one or more performance obligations that are either (1) capable of being distinct (i.e., the customer can benefit from the product or service on its own or together with readily available resources, including those purchased separately from us) and distinct within the context of the contract (i.e., separately identified from other promises in the contract) or (2) a series of distinct products or services that are substantially the same and have the same pattern of transfer to the customer. Our term license subscriptions are delivered at a point in time while our cloud subscriptions, maintenance and support, and professional services are delivered over time. Subscriptions Revenue Subscriptions revenue is primarily related to (1) cloud subscriptions bundled with maintenance and support and hosting services and (2) term license subscriptions bundled with maintenance and support. We generally charge subscription fees on a per-user basis or through non-user based single application licenses. We bill customers and collect payment for subscriptions to 74 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS our platform in advance on an annual, quarterly, or monthly basis. In certain instances, our customers have paid their entire contract up front. Cloud Subscriptions We generate cloud-based subscriptions revenue primarily from the sales of subscriptions to access our cloud offering, together with related support services to our customers. We perform all required maintenance and support for our cloud offering. Revenue is recognized on a ratable basis over the contract term beginning on the date the service is made available to the customer. Our cloud-based subscription contracts generally have a term of one to three years in length. We bill customers and collect payment for subscriptions to our platform in advance, and they are non-cancellable. Term License Subscriptions Our term license subscription revenue is derived from customers with on-premises installations of our platform. The majority of our contracts are one year in length. Although term license subscriptions are sold with maintenance and support, the software is fully functional at the beginning of the subscription and is considered a distinct performance obligation. If a cloud agreement includes the right for the customer to take possession of the license, the revenue is treated as a term license. Revenue from term license subscriptions is recognized when control of the software license has transferred to the customer, which is the later of delivery or commencement of the contract term. Maintenance and Support Maintenance and support subscriptions include both technical support and when-and-if-available software upgrades, which are treated as a single performance obligation as they are considered a series of distinct services that are substantially the same and have the same duration and measure of progress. Revenue from maintenance and support is recognized ratably over the contract period, which is the period over which the customer has continuous access to maintenance and support. Professional Services Revenue Our professional services revenue is comprised of fees for consulting services, including application development and deployment assistance as well as training services related to our platform. Consulting Services We sell consulting services to assist customers in planning and executing the deployment of our software. Customers are not required to use consulting services to fully benefit from the software. Consulting services are regularly sold on a standalone basis and either (1) under a fixed-fee arrangement or (2) on a time and materials basis. Consulting service contracts are considered separate performance obligations because they do not integrate with each other or with other products and services to deliver a combined output to the customer, do not modify or customize (or are not modified or customized by) each other or other products and services, and do not affect the customer's ability to use the other consulting offerings or other products and services. Revenue under consulting contracts is recognized over time as services are delivered. For time and materials-based consulting contracts, we have elected the practical expedient of recognizing revenue upon invoicing since the invoiced amount corresponds directly to the value of our service to date. Training Services We sell various training services to our customers. Training services are sold in the form of prepaid training credits that are redeemed based on a fixed rate per course. Training revenue is recognized when the associated training services are delivered. Significant Judgments and Estimates Determining the Transaction Price The transaction price is the total amount of consideration we expect to receive in exchange for the service offerings in a contract and may include both fixed and variable components. Variable consideration is included in the transaction price to the 75 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS extent it is probable a significant reversal will not occur. The amount of variable consideration excluded from the transaction price for the years ended December 31, 2022, 2021, and 2020 was insignificant. Our estimates of variable consideration are also subject to subsequent true-up adjustments and may result in changes to transaction prices; however, such true-up adjustments are not expected to be material. Allocating the Transaction Price Based on Standalone Selling Prices (“SSP”) We allocate the transaction price to each performance obligation in a contract based on its relative SSP. The SSP is the observable price at which we sell the product or service separately. In the absence of observable pricing, we estimate SSP using the residual approach. We establish SSP as follows: 1. Cloud subscriptions - Given the highly variable selling price of our cloud subscriptions, we establish the SSP of our cloud subscriptions using a residual approach after first determining the SSP of consulting and training services. We have concluded the residual approach to estimating SSP of our cloud subscriptions is an appropriate allocation of the transaction price. 2. Term license subscriptions - Given the highly variable selling price of our term license subscriptions, we have established SSP of term license subscriptions using a residual approach after first determining the SSP of maintenance and support. Maintenance and support is sold on a standalone basis in conjunction with renewals of our legacy perpetual software licenses and within a narrow range of the net license fee. Because an economic relationship exists between the license and maintenance and support, we have concluded the residual approach to estimating SSP of term license subscriptions is an appropriate allocation of the transaction price. 3. Maintenance and support - We establish the SSP of maintenance and support as a percentage of the stated net subscription fee based on observable pricing of maintenance and support renewals from our legacy perpetual software licenses. 4. Consulting and training services - The SSP of consulting and training services is established based on the observable pricing of standalone sales within each geographic region where the services are sold. Contract Balances Timing may differ between the satisfaction of performance obligations and the invoicing and collection of amounts related to our contracts with customers. Contract assets primarily relate to unbilled amounts for contracts with customers for which the amount of revenue recognized exceeds the amount billed to the customer. Contract assets are transferred to accounts receivable when the right to invoice becomes unconditional. As of December 31, 2022 and 2021, contract assets of $ 14.3 million and $ 14.0 million, respectively, are included in the Prepaid expenses and other current assets and Other assets line items in our consolidated balance sheets. Contract liabilities consist of deferred revenue and include payments received in advance of the satisfaction of performance obligations. Deferred revenue is then recognized as the revenue recognition criteria are met. Deferred revenue that will be recognized during the succeeding 12-month period is recorded as current, and the remaining deferred revenue is recorded as non-current. For the year ended December 31, 2022, we recognized $ 147.0 million of revenue that was included in the deferred revenue balance as of December 31, 2021. Transaction Price Allocated to the Remaining Performance Obligations As of December 31, 2022, we had an aggregate transaction price of $ 376.5 million allocated to unsatisfied performance obligations. We expect to recognize $ 243.2 million of this balance as revenue over the next 12 months with the remaining amount recognized thereafter. 4. Leases As of December 31, 2022, our lease portfolio consists entirely of operating leases, all of which are for corporate offices. Our operating leases have remaining lease terms with various expiration dates through 2031, and some leases include options to extend the term for up to an additional 10 years. 76 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Right-of-Use (“ROU”) Assets and Lease Liabilities At the inception of an arrangement, we determine whether the arrangement is or contains a lease based on the unique facts and circumstances present and the classification of the lease. Operating leases with a term greater than one year are recognized on the consolidated balance sheet as ROU assets, lease liabilities, and, if applicable, long-term lease liabilities. ROU assets represent our right to use an underlying asset for the lease term, and lease liabilities represent our obligation to make lease payments arising from the lease. We have elected not to recognize on our consolidated balance sheets leases with a term of one year or less. Lease liabilities and their corresponding ROU assets are recorded based on the present value of lease payments over the expected lease term. The implicit rates within most of our leases are generally not determinable; therefore, we estimate our incremental borrowing rate to determine the present value of lease payments. The determination of our incremental borrowing rate requires judgment and is estimated for each lease based on the rate we would have to pay for a collateralized loan with the same terms as the lease. We consider various factors, including our level of collateralization, estimated credit rating, and the currency in which the lease is denominated. Operating lease ROU assets also include any lease prepayments, offset by lease incentives. Certain of our leases include options to extend or terminate the lease. An option to extend the lease is considered in connection with determining the ROU asset and lease liability when it is reasonably certain we will exercise that option.. Lease Costs Expense for operating leases is recognized on a straight-line basis over the lease term as an operating expense. We have lease agreements which require payments for lease and non-lease components (i.e., common area maintenance) that are accounted for as a single lease component. Variable lease payment amounts that cannot be determined at the commencement of the lease, such as maintenance costs based on future obligations, are not included in ROU assets or lease liabilities but rather are expensed as incurred and recorded as variable lease expense. The following table sets forth the components of lease expense for the years ended December 31, 2022, 2021 and 2020 (in thousands): Year Ended December 31, 2022 2021 2020 Operating lease cost $ 6,950 $ 6,619 $ 6,649 Finance lease costs: Amortization of right-of-use assets — — 1,242 Interest on lease liabilities — — 150 Short-term lease cost 583 149 565 Variable lease cost 3,817 2,713 281 Total $ 11,350 $ 9,481 $ 8,887 77 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Supplemental Lease Information Supplemental balance sheet information related to operating leases as of December 31, 2022 and December 31, 2021 is as follows (in thousands, except for lease term and discount rate): As of December 31, 2022 2021 Right-of-use assets for operating leases $ 37,248 $ 27,897 Operating lease liabilities, current $ 8,681 $ 8,110 Operating lease liabilities, net of current portion 57,225 48,784 Total operating lease liabilities $ 65,906 $ 56,894 Weighted average remaining lease term (in years) 8.4 9.5 Weighted average discount rate 9.4 % 9.5 % Supplemental cash flow and expense information related to operating leases for the years ended December 31, 2022 and 2021 is as follows (in thousands): Year Ended December 31, 2022 2021 2020 Operating cash outflows for operating leases $ 7,073 $ 7,732 $ 3,407 Operating cash outflows for finance leases — — 150 Financing cash outflows for finance leases — — 3,822 Amortization of operating lease ROU assets 1,495 1,361 1,554 Interest expense on operating lease liabilities 5,406 5,268 1,853 A summary of our future minimum lease commitments under non-cancellable leases as of December 31, 2022 is as follows (in thousands): Operating Leases 2023 $ 9,076 2024 11,122 2025 11,409 2026 11,666 2027 11,717 Thereafter 42,513 Total lease payments 97,503 Less: imputed interest ( 31,597 ) Total $ 65,906 5. Business Combinations In August 2021, we acquired 100 % of the outstanding common stock of Lana Labs, a developer of process mining software, for approximately $ 30.7 million, net of cash acquired and debt. The acquisition was made due to the attractive nature 78 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS of the product offerings of Lana Labs and in furtherance of our objective to enhance our automation platform. The transaction was financed through available cash on hand. The allocation of the purchase price was based upon the fair value of the assets acquired and liabilities assumed. The purchase price allocated to goodwill and intangible assets is not deductible for tax purposes. The following table summarizes the fair value of the assets acquired and liabilities assumed in connection with the acquisition (in thousands): Cash acquired $ 256 Other current assets 106 Property and equipment 59 Developed technology 5,974 Customer relationships 750 Goodwill 24,521 Other non-current assets 27 Total assets acquired 31,693 Current liabilities 638 Non-current liabilities 38 Total liabilities assumed 676 Net assets acquired $ 31,017 During the third quarter of 2022, we finalized the fair value of the assets acquired and liabilities assumed in the acquisition, and the amounts presented above are now final. Measurement period adjustments recorded in 2021 included a $ 0.8 million adjustment to developed technology and goodwill related to an update to the discount rate utilized in our valuation of intangible assets, a $ 0.3 million increase in deferred revenue stemming from our early adoption of new accounting guidance relating to deferred revenue recognized pursuant to a business combination, a $ 0.1 million deferred tax adjustment, and an immaterial adjustment to working capital. 6. Goodwill and Intangible Assets The following table summarizes goodwill balances as of December 31, 2022 and 2021 (in thousands): Carrying Amount Balance as of December 31, 2020 $ 4,862 Goodwill acquired, net of measurement period adjustments 24,521 Foreign currency translation adjustments ( 1,588 ) Balance as of December 31, 2021 $ 27,795 Goodwill acquired — Foreign currency translation adjustments ( 1,446 ) Balance as of December 31, 2022 $ 26,349 79 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Intangible assets, net consisted of the following as of December 31, 2022 and 2021 (in thousands): As of December 31, 2022 2021 Developed technology $ 6,893 $ 7,271 Customer relationships - Non-Robotic Process Automation (“RPA”) 827 872 Customer relationships - RPA 246 261 Intangible assets, gross 7,966 8,404 Less: Accumulated amortization ( 2,715 ) ( 1,260 ) Intangible assets, net $ 5,251 $ 7,144 Intangible amortization expense was $ 1.5 million, $ 0.8 million, and $ 0.4 million for the years ended December 31, 2022, 2021, and 2020, respectively. As of December 31, 2022, the weighted average remaining amortization periods for developed technology, non-RPA customer relationships, and RPA customer relationships were approximately 3.4 years, 8.7 years, and 7.0 years, respectively. The projected annual amortization expense related to amortizable intangible assets as of December 31, 2022 is as follows (in thousands): Year Ended December 31, 2023 $ 1,471 2024 1,471 2025 1,170 2026 753 2027 92 Thereafter 294 Total projected amortization expense $ 5,251 7. Property and Equipment, net Property and equipment, net consisted of the following as of December 31, 2022 and 2021 (in thousands): As of December 31, 2022 2021 Leasehold improvements $ 45,959 $ 41,005 Office furniture and fixtures 3,476 2,536 Computer hardware 9,689 6,001 Computer software 1,353 1,353 Equipment 242 124 Property and equipment, gross 60,719 51,019 Less: Accumulated depreciation ( 18,864 ) ( 14,106 ) Property and equipment, net $ 41,855 $ 36,913 Depreciation expense totaled $ 5.8 million, $ 4.9 million, and $ 5.4 million for the years ended December 31, 2022, 2021, and 2020, respectively. During the year ended December 31, 2022, we retired and disposed of fully depreciated laptops and computer hardware with a gross asset value of approximately $ 1.0 million. Disposals during the year ended December 31, 2021 were not significant. 80 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 8. Accrued Expenses Accrued expenses consisted of the following as of December 31, 2022 and 2021 (in thousands): As of December 31, 2022 2021 Hosting costs $ 2,802 $ 1,995 Contract labor costs 1,465 891 Marketing and tradeshow expenses 1,000 1,167 Audit and tax expenses 911 439 Taxes payable 827 550 Legal costs 475 5,511 Reimbursable employee expenses 1,004 870 Third party license fees 1,223 1,066 Capital expenditures 744 379 Other accrued expenses 1,776 2,615 Total $ 12,227 $ 15,483 9. Debt Senior Secured Credit Facilities Credit Agreement On November 3, 2022, we entered into a new Senior Secured Credit Facilities Credit Agreement (the “Credit Agreement”) which provides for a five-year term loan facility in an aggregate principal amount of $ 100.0 million and, in addition, up to $ 50.0 million for a revolving credit facility, including a letter of credit sub-facility in the aggregate availability amount of $ 15.0 million and a swingline sub-facility in the aggregate availability amount of $ 10.0 million (as a sublimit of the revolving loan facility). On December 13, 2022, we executed the first amendment to the credit agreement which increased the aggregate principal amount of the term loan facility by $ 20.0 million and the limit of the revolving credit facility by $ 10.0 million. The Credit Agreement matures on November 3, 2027. We will use the proceeds from the $ 120.0 million term loan to fund the continued growth of our business and support our working capital requirements. Under the agreement, we may elect whether amounts drawn bear interest on the outstanding principal amount at a rate per annum equal to either (a) the higher of the Prime rate or the Federal Funds Effective (“Base Rate”) rate plus 0.50 % or (b) the forward-looking term rate based on the secured overnight financing rate (“Term SOFR”). An additional interest rate margin is added to the elected interest rates. During the first three years of the Credit Agreement, the additional interest rate margin ranges from 1.5 % to 2.5 % in the case of Base Rate advances or from 2.5 % to 3.5 % in the case of Term SOFR advances, depending on our debt to recurring revenue leverage ratio (as defined in the Credit Agreement). During the final two years of the Credit Agreement, the interest rate margin ranges from 0.5 % to 2.5 % in the case of Base Rate advances and from 1.5 % to 3.5 % in the case of Term SOFR advances, depending on our debt to consolidated adjusted EBITDA leverage ratio (as defined in the Credit Agreement). In addition, the Credit Agreement contains other customary representations, warranties and covenants, including covenants by us limiting additional indebtedness, guaranties, liens, fundamental changes, mergers and consolidations, dispositions of assets, investments, paying dividends on capital stock or redeeming, repurchasing or retiring capital stock, or prepaying certain junior indebtedness and preferred stock , certain corporate changes, and transactions with affiliates. The Credit Agreement also provides for customary events of default, including but not limited to non-payment, breaches or defaults in the performance of covenants, insolvency, bankruptcy, and the occurrence of a material adverse effect on us. 81 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS The following table summarizes outstanding long-term debt balances (in thousands): As of December 31, 2022 2021 Secured term loan facility $ 119,375 $ — Less: Debt issuance costs ( 1,256 ) — Total long-term debt, net of debt issuance costs $ 118,119 $ — Long-term debt, current $ 2,740 $ — Long-term debt, net of current portion 115,379 — Total long-term debt $ 118,119 $ — The following table summarizes the annual maturities of the principal amount of total debt due (in thousands): Repayment schedule of principal long-term debt as of December 31, 2022 2023 $ 3,000 2024 3,750 2025 6,000 2026 6,000 2027 100,625 Total $ 119,375 We were in compliance with all covenants as of December 31, 2022. As of December 31, 2022, we had no outstanding borrowings under the revolving credit facility, and we had outstanding letters of credit totaling $ 12.0 million in connection with securing our leased office space. 10. Income Taxes For the years ended December 31, 2022, 2021, and 2020, our loss before income taxes was comprised of the following (in thousands): Year Ended December 31, 2022 2021 2020 Domestic $ ( 102,434 ) $ ( 48,743 ) $ ( 25,463 ) Foreign ( 47,794 ) ( 39,120 ) ( 7,131 ) Total $ ( 150,228 ) $ ( 87,863 ) $ ( 32,594 ) 82 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS For the years ended December 31, 2022, 2021, and 2020, our income tax expense (benefit) was comprised of the following (in thousands): Year Ended December 31, 2022 2021 2020 Current: Federal $ 72 $ 15 $ 11 State 119 79 79 Foreign 1,409 1,156 977 Total current expense 1,600 1,250 1,067 Deferred: Federal — — — State — — — Foreign ( 908 ) ( 472 ) ( 184 ) Total deferred benefit ( 908 ) ( 472 ) ( 184 ) Total income tax expense $ 692 $ 778 $ 883 For the years ended December 31, 2022, 2021, and 2020, the provision for income taxes differs from the amount computed by applying the federal statutory income tax rates to our loss before the provision (benefit) for income taxes as follows: Year Ended December 31, 2022 2021 2020 U.S. federal statutory tax rate 21.0 % 21.0 % 21.0 % State tax expense 4.1 4.7 18.2 Foreign rate differential ( 3.3 ) ( 4.1 ) ( 3.6 ) Nondeductible expenses ( 0.3 ) ( 0.5 ) ( 0.6 ) Foreign tax expense 0.3 ( 0.2 ) — Equity compensation 1.0 7.0 46.2 Tax credits 4.7 5.0 12.0 Unrecognized tax benefits ( 0.9 ) ( 0.9 ) ( 2.2 ) Change in tax rate 0.3 ( 1.2 ) — Other ( 0.5 ) ( 0.1 ) ( 1.1 ) Deferred adjustments ( 0.8 ) 0.9 ( 1.7 ) Change in valuation allowance ( 26.1 ) ( 32.5 ) ( 90.9 ) Total ( 0.5 ) % ( 0.9 ) % ( 2.7 ) % The effective tax rate of ( 0.5 )% in 2022 includes $ 39.2 million of tax expense attributable to the change in the valuation allowance in the United States, Switzerland, and Germany (Lana Labs GmbH), partially offset by $ 8.6 million of favorable excess tax benefits for equity compensation and research credits. 83 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Deferred tax assets and liabilities reflect the net tax effects of temporary differences between the carrying amount of the assets and liabilities for financial reporting purposes and the amounts used for income tax purposes. As of December 31, 2022 and 2021, significant components of our deferred tax assets and liabilities were as follows (in thousands): As of December 31, 2022 2021 Deferred tax assets: Net operating losses $ 85,442 $ 81,499 Tax credits 21,215 15,510 Deferred revenue 416 466 Equity compensation 5,314 4,917 Lease liabilities 17,732 15,089 Accrued compensation 4,510 3,390 Bad debt 656 373 Other accrued expense 16 1,452 Capitalized research and development costs 29,991 — Other 431 301 Gross deferred tax assets 165,723 122,997 Less: Valuation allowance ( 132,581 ) ( 94,399 ) Total deferred tax assets 33,142 28,598 Deferred tax liabilities: Prepaid expenses ( 15,309 ) ( 12,576 ) Right-of-use assets ( 10,056 ) ( 7,361 ) Unbilled receivables — ( 1,248 ) Depreciation ( 4,275 ) ( 3,892 ) Intangible assets ( 1,540 ) ( 2,102 ) Other ( 123 ) ( 603 ) Total deferred tax liabilities ( 31,303 ) ( 27,782 ) Net deferred tax assets $ 1,839 $ 816 As of December 31, 2022 and 2021, we had $ 237.7 million and $ 239.9 million of gross net operating loss (“NOL”) carryforwards for U.S. federal tax purposes, respectively. U.S. federal NOL carryforwards in the amount of $ 16.9 million, gross, generated prior to 2018 will expire, if unused, in 2037. Under the Tax Cuts and Jobs Act of 2017 (the “TCJA”), as modified by the Coronavirus Aid, Relief, and Economic Security Act (the “CARES Act”), federal NOL carryforwards generated in tax years beginning after December 31, 2017 may be carried forward indefinitely. As of December 31, 2022, we had $ 220.8 million of gross NOL carryforwards generated after 2017 for U.S. federal tax purposes, which may be used to offset 80% of our taxable income annually. Section 382 of the Internal Revenue Code limits the utilization of NOL carryforwards when ownership changes occur, as defined by that section. A number of states have similar state laws that limit utilization of state NOL carryforwards when ownership changes occur. We have performed an analysis of our Section 382 ownership changes and have determined all U.S. federal and state NOL carryforwards are available for use as of December 31, 2022. Beginning in 2022, the TCJA eliminated the option to deduct research and development expenditures immediately in the year incurred and requires companies to amortize such expenditures over five or fifteen years for tax purposes, depending on whether the activities were incurred in the U.S. or outside of the U.S. This change resulted in an increase to gross deferred tax assets of approximately $ 30.0 million in 2022. Due to the full valuation allowance recorded against our U.S. deferred tax assets, there was no impact to net deferred tax assets. Additionally, there was no cash tax impact for 2022 due to our ability to use NOL carryforwards to fully offset taxable income generated by the changes to research and development expenditures. 84 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS As of December 31, 2022 and 2021, we had $ 19.3 million and $ 13.7 million, respectively, of U.S. federal tax credit carryforwards which will expire, if unused, between 2031 and 2042. As of December 31, 2022 and 2021, we had U.S. gross state NOL carryforwards of $ 256.3 million and $ 249.8 million, respectively. We had tax effected state NOL carryforwards of $ 14.8 million and $ 14.1 million as of December 31, 2022 and 2021, respectively. The rules regarding carryforwards vary from state to state, and the ability to utilize NOLs varies based on timing and amount. The majority of state NOL carryforwards generated prior to 2018 will expire, if unused, in 2037. Due to the TCJA, certain state NOL carryforwards generated after 2017 have an indefinite carryforward period. As of December 31, 2022 and 2021, we had foreign gross NOL carryforwards of $ 163.4 million and $ 126.6 million, respectively, primarily attributable to our subsidiary in Switzerland. In 2022, $ 8.1 million of Swiss NOLs expired related to the 2015 tax year. An additional piece of those NOL carryforwards will expire each year, if unused, between 2023 and 2029. The net change in the total valuation allowance during the year ended December 31, 2022 was $ 38.2 million, primarily driven by the valuation allowance recorded against the United States and Switzerland deferred tax assets. The $ 1.1 million valuation allowance against the Germany (Lana Labs GmbH) deferred tax assets was released in 2022 as a result of post-integration tax planning and the merger of German subsidiaries. As of December 31, 2022, we continued to maintain a full valuation allowance against U.S. deferred tax assets based on our cumulative operating results as of December 31, 2022, three-year cumulative loss, and an assessment of our expected future results of operations. We have evaluated all evidence, both positive and negative, in assessing the likelihood of realizability, and we determined the negative evidence outweighed the positive evidence. As of December 31, 2022, we have a valuation allowance of $ 18.7 million against foreign deferred tax assets at our subsidiary in Switzerland. Based on our cumulative operating results as of December 31, 2022 and assessment of our expected future results of operations, we determined it was not more likely than not we would be able to realize the deferred tax assets prior to expiration. We plan to distribute previously undistributed earnings of our foreign subsidiaries back to the United States in future years. Upon repatriation of those earnings, if any, we may be subject to taxes, including withholding taxes, net of any applicable foreign tax credits. Determination of the amount of unrecognized deferred U.S. income tax liability is not practicable. As of December 31, 2022 and 2021, we had unrecognized tax benefits of $ 4.5 million and $ 3.1 million, respectively, none of which would affect our effective tax rate if recognized due to the valuation allowance. The following table summarizes the activity related to our unrecognized tax benefit from December 31, 2019 to December 31, 2022 (in thousands): 85 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Balance as of December 31, 2019 $ 1,575 Additions for tax positions in current years 702 Additions for tax positions in prior years — Reductions due to lapse in statutes of limitations — Settlements — Balance as of December 31, 2020 2,277 Additions for tax positions in current years 812 Additions for tax positions in prior years — Reductions due to lapse in statutes of limitations — Settlements — Balance as of December 31, 2021 3,089 Additions for tax positions in current years 1,399 Additions for tax positions in prior years — Reductions due to lapse in statutes of limitations — Settlements — Balance as of December 31, 2022 $ 4,488 We recognize interest and penalties related to uncertain tax positions in income tax expense. During the years ended December 31, 2022, 2021, and 2020, we recognized nominal amounts in interest. The cumulative balance of interest and penalties as of December 31, 2022 and 2021 were not meaningful. We anticipate total unrecognized tax benefits will not decrease over the next year. We file income tax returns in the U.S. federal jurisdiction and in various state and foreign jurisdictions. Due to the NOL carryforward, tax years 2016 through 2022 remain open to examination by the major taxing jurisdictions to which we are subject. There are no open examinations that would have a meaningful impact to our consolidated financial statements. 11. Stock-Based Compensation Equity Incentive Plans In May 2017, our Board of Directors adopted, and our stockholders approved, the 2017 Equity Incentive Plan (the “2017 Plan”), which became effective as of the date of the final prospectus for our initial public offering. The 2017 Plan provides for the grant of incentive stock options to employees and for the grant of nonstatutory stock options, restricted stock awards, restricted stock units (“RSUs”), stock appreciation rights, performance-based stock awards, and other forms of equity compensation to employees, including officers, non-employee directors, and consultants. We initially reserved 6,421,442 shares of Class A common stock for issuance under the 2017 Plan, which included 421,442 shares that remained available for issuance under our 2007 Stock Option Plan (the “2007 Plan”) at the time the 2017 Plan became effective. The number of shares reserved under the 2017 Plan increases for any shares subject to outstanding awards originally granted under the 2007 Plan that expire or are forfeited prior to exercise. As a result of the adoption of the 2017 Plan, no further grants may be made under the 2007 Plan. As of December 31, 2022, there were 7,196,149 shares of Class A common stock reserved for issuance under the 2017 Plan, of which 2,839,475 were available to be issued. Stock Options We estimate the fair value of stock options containing only a service condition using the Black-Scholes option pricing model, which requires the use of subjective assumptions, including the expected term of the option, the current price of the underlying stock, the expected stock price volatility, expected dividend yield, and the risk-free interest rate for the expected term of the option. The expected term represents the period of time the stock options are expected to be outstanding. Due to the lack of sufficient historical exercise data to provide a reasonable basis upon which to derive an estimate, we use the simplified method to estimate the expected term for our stock options. Under the simplified method, the expected term of an option is presumed to be the mid-point between the vesting date and the end of the contractual term. Expected volatility is based on the 86 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS historical volatility of our publicly traded stock over the estimated expected term of the stock options. We assume zero dividend yield because we have historically not paid dividends and do not anticipate paying dividends in the near future. In June 2022, our Board of Directors granted a stock option to purchase 700,000 shares of our Class A common stock to our Chief Executive Officer (the “2022 CEO Grant”) under the 2017 Plan with an exercise price of $ 50.63 per share. The 2022 CEO Grant is eligible to vest based on the achievement of various stock price appreciation targets of our Class A common stock. Specifically, the 2022 CEO Grant vests in four installments of 25 % each if the average closing price per share for a 365 day calendar period equals each of $ 175 , $ 200 , $ 225 , and $ 250 , respectively (the “Vesting Price Threshold”), prior to June 7, 2030. The option also vests if the Company engages in a Corporate Transaction, as defined in the Plan, in which the Company’s Class A common stock is valued at or above the Vesting Price Threshold. The fair value of the 2022 CEO Grant was determined using a Monte Carlo simulation. The fair value of the award at the grant date was $ 18.8 million and is being amortized over derived service periods ranging from 3.4 years to 4.1 years. The only stock option awarded during the years ended December 31, 2022, 2021, and 2020 was the 2022 CEO Grant. The following table summarizes the assumptions used to estimate the fair value of the 2022 CEO stock option grant: Year Ended December 31, 2022 2021 2020 Risk-free interest rate 3.01 % * * Expected term (in years) ** * * Expected volatility 70 % * * Expected dividend yield — % * * * Not applicable because no stock options were granted during the period. ** Each Vesting Price Threshold for the 2022 CEO grant has a unique expected term ranging from 3.4 years to 4.1 years. The following table summarizes stock option activity for the years ended December 31, 2022, 2021, and 2020: Number of Shares Weighted Average Exercise Price Weighted Average Remaining Contractual Term (Years) Aggregate Intrinsic Value (in thousands) Outstanding at December 31, 2019 4,458,611 $ 12.30 5.8 $ 115,501 Granted — — Exercised ( 1,001,411 ) 6.39 81,181 Expired ( 1,380 ) 11.82 Forfeited ( 56,580 ) 11.33 Outstanding at December 31, 2020 3,399,240 14.06 4.9 503,174 Granted — — Exercised ( 423,824 ) 6.55 43,525 Expired ( 4,100 ) 10.54 Forfeited ( 17,960 ) 11.78 Outstanding at December 31, 2021 2,953,356 15.16 4.0 147,812 Granted 700,000 50.63 Exercised ( 937,217 ) 27.14 32,858 Expired ( 7,900 ) 4.06 Forfeited ( 10,280 ) 12.28 Outstanding at December 31, 2022 2,697,959 $ 20.25 5.1 $ 45,867 Exercisable at December 31, 2022 1,997,959 $ 9.60 3.6 $ 45,867 87 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS The total fair value of stock options that vested during the years ended December 31, 2022, 2021, and 2020 was $ 0.9 million, $ 10.8 million, and $ 2.8 million, respectively. As of December 31, 2022, the total compensation cost related to unvested stock options not yet recognized, which relates exclusively to the 2022 CEO Grant, was $ 16.0 million. This amount will be recognized over a weighted average period of 3.19 years. Restricted Stock Units The following table summarizes RSU activity for the years ended December 31, 2022, 2021, and 2020: Number of Shares Weighted Average Grant Date Fair Value Non-vested and outstanding at December 31, 2019 1,022,835 $ 31.39 Granted 589,692 60.47 Vested ( 270,609 ) 31.29 Forfeited ( 176,915 ) 32.01 Non-vested and outstanding at December 31, 2020 1,165,003 46.04 Granted 488,462 108.98 Vested ( 354,130 ) 43.39 Forfeited ( 89,806 ) 62.72 Non-vested and outstanding at December 31, 2021 1,209,529 70.99 Granted 606,203 52.63 Vested ( 403,648 ) 58.63 Forfeited ( 221,364 ) 70.30 Non-vested and outstanding at December 31, 2022 1,190,720 $ 65.97 As of December 31, 2022, total unrecognized compensation cost related to unvested RSUs was approximately $ 58.3 million, which will be recognized over a weighted average period of 1.6 years. The following table summarizes the components of our stock-based compensation expense by instrument type for the years ended December 31, 2022, 2021, and 2020 (in thousands): Year Ended December 31, 2022 2021 2020 RSUs $ 35,290 $ 19,382 $ 10,745 Stock options 2,790 3,839 4,164 Common stock awards to Board of Directors 750 623 370 Total stock-based compensation expense $ 38,830 $ 23,844 $ 15,279 88 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Stock-based compensation expense for RSUs, stock options, and issuances of common stock to the Board of Directors is included in the following line items in the accompanying consolidated statements of operations for the years ended December 31, 2022, 2021, and 2020 (in thousands): Year Ended December 31, 2022 2021 2020 Cost of revenue Subscriptions $ 996 $ 1,199 $ 943 Professional services 5,309 3,131 1,477 Operating expenses Sales and marketing 9,152 5,426 2,821 Research and development 12,523 5,224 2,718 General and administrative 10,850 8,864 7,320 Total stock-based compensation expense $ 38,830 $ 23,844 $ 15,279 12. Stockholders' Equity As of December 31, 2022, we had authorized 500,000,000 shares of Class A common stock and 100,000,000 shares of Class B common stock, each with a par value of $ 0.0001 per share, of which 41,320,091 shares of Class A common stock and 31,497,796 shares of Class B common stock were issued and outstanding. The rights of the holders of Class A common stock and Class B common stock are identical, except with respect to voting and conversion rights. The holders of Class A common stock are entitled to one vote per share, and the holders of Class B common stock are entitled to ten votes per share on all matters subject to stockholder vote. The holders of Class B common stock also have approval rights for certain corporate actions. Each share of Class B common stock may be converted into one share of Class A common stock at the option of its holder and will be automatically converted upon transfer thereof, subject to certain exceptions. In addition, upon the date on which the outstanding shares of Class B common stock represent less than 10 % of the aggregate voting power of our capital stock, all outstanding shares of Class B common stock shall convert automatically into Class A common stock. 13. Basic and Diluted Loss per Common Share The following table sets forth the computation of basic and diluted net loss per share for the years ended December 31, 2022, 2021, and 2020 (in thousands, except share and per share data): Year Ended December 31, 2022 2021 2020 Numerator: Net loss $ ( 150,920 ) $ ( 88,641 ) $ ( 33,477 ) Denominator: Weighted average common shares outstanding, basic and diluted 72,455,175 71,036,490 69,050,565 Net loss per share, basic and diluted $ ( 2.08 ) $ ( 1.25 ) $ ( 0.48 ) Due to net losses for the years ended December 31, 2022, 2021, and 2020, basic and diluted net loss per share were the same as the effect of potentially dilutive securities would have been antidilutive. The following outstanding securities, prior to the use of the treasury stock method, have been excluded from the computation of diluted weighted-average shares outstanding for the respective periods below because they would have been antidilutive to earnings per share: 89 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Year Ended December 31, 2022 2021 2020 Stock options 2,697,959 2,953,356 3,399,240 Non-vested restricted stock units 1,190,720 1,209,529 1,165,003 14. Commitments and Contingencies Minimum Purchase Commitments In July 2021, we executed a non-cancellable cloud hosting arrangement with Amazon Web Services (“AWS”) that contains provisions for minimum purchase commitments. Specifically, purchase commitments under the agreement total $ 131.0 million over five years, including $ 22.0 million in the first year, $ 25.0 million in the second year, and $ 28.0 million in each of the third, fourth, and fifth years. The timing of payments under the agreement may vary, and the total amount of payments may exceed the minimum depending on the volume of services utilized. Spending under this agreement for the year ended December 31, 2022 totaled $ 33.1 million. Letters of Credit At December 31, 2022 and 2021, we had outstanding letters of credit totaling $ 12.0 million and $ 11.2 million, respectively, in connection with securing our leased office space. All letters of credit are secured by our current or historical borrowing arrangements as described in Note 9. Pegasystems Litigation On May 29, 2020, we filed a civil complaint against Pegasystems, Inc. (“Pegasystems”) and Youyong Zou, a Virginia resident, in the Circuit Court for Fairfax County, Virginia. Appian Corp v. Pegasystems Inc. & Youyong Zou, No. 2020-07216 (Fairfax Cty. Ct.) . On May 10, 2022, we announced the jury awarded us $ 2.036 billion in damages for misappropriation of our trade secrets and $ 1 in damages for violating the Virginia Computer Crimes Act. Pegasystems filed several post-trial motions seeking relief in the form of reducing the damages award or setting aside the jury’s verdict and either granting a new trial or entering judgment in Pegasystems’ favor. All of these motions were denied, and final judgment was entered by the Court on September 15, 2022. The final judgment reaffirmed the $ 2.036 billion in damages and also ordered Pegasystems to pay Appian $ 23.6 million in attorney's fees associated with the case as well as statutory post-judgment interest on the judgment at an annual rate of 6 %, or approximately $ 122.0 million per year. Defendant Youyong Zou has satisfied the judgment of $ 5,000 (plus interest) against him in lieu of appealing that judgment. On September 15, 2022, Pegasystems filed a notice of appeal, and on February 6, 2023, Pegasystems filed its opening brief with the Court of Appeals of Virginia. Appian expects to file its responsive brief in March 2023, to which Pegasystems will file a reply brief. After submission of the reply brief, the timeline of the case is solely within the control of the Court of Appeals until it rules. Pegasystems is not required to pay us the judgment, attorney’s fees, or post-judgment interest until all appeals are exhausted. We cannot predict the outcome of any appeals or the time it will take to resolve them. Consistent with other judgments, there is no guarantee we will be able to collect all or any portion of the judgment. Consequently, we will not record the award in our consolidated financial statements until all contingencies are resolved and we collect on the judgment. Other Legal Matters From time to time, we are subject to legal, regulatory, and other proceedings and claims that arise in the ordinary course of business. Other than as disclosed elsewhere in this Annual Report, we are not presently a party to any legal proceedings that, if determined adversely to us, would individually or taken together have a material adverse effect on our business, operating results, financial condition, or cash flows. We do not believe any material liability will be imposed as a result of any of the foregoing matters. 90 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 15. Segment and Geographic Information The following table summarizes revenue by geography for the years ended December 31, 2022, 2021, and 2020 (in thousands): Year Ended December 31, 2022 2021 2020 Domestic $ 311,075 $ 243,562 $ 201,483 International 156,916 125,697 103,090 Total $ 467,991 $ 369,259 $ 304,573 With respect to geographic information, revenue is attributed to respective geographies based on the contracting address of the customer. There were no individual foreign countries from which more than 10% of our total revenue was attributable for the years ended December 31, 2022 and 2021. Revenue from customers attributed to the United Kingdom were 12.5 % of our total revenue for the year ended December 31, 2020. Substantially all of our long-lived assets were held in the United States as of December 31, 2022 and 2021. 16. Retirement Plans We have a defined contribution 401(k) retirement and savings plan (the “Plan”) to provide retirement benefits for all eligible employees. With limited exceptions, all employees over the age of 21 on the first day of the month immediately following the month of hiring are eligible to participate in the Plan. The Plan allows eligible employees to make salary-deferred contributions up to 75 % of their pre-tax annual compensation, as defined in the Plan, as long as the total contributed does not exceed the annual maximum allowable amount under the Internal Revenue Code. The Company makes a semi-monthly matching contribution of 100 % of the employee's contribution for that pay period, up to a maximum of 4 % of the employee's eligible gross compensation for that pay period. Company contributions vest ratably based on years of service over a four year period, beginning with the completion of the first year of service. For the years ended December 31, 2022, 2021, and 2020, we incurred $ 11.5 million, $ 8.7 million, and $ 6.8 million, respectively, in contribution expense related to employer matching contributions. 17. Investments and Fair Value Measurements Fair Value Measurements U.S. GAAP establishes a three-tier fair value hierarchy to classify and disclose all assets and liabilities measured at fair value on a recurring basis, as well as assets and liabilities measured at fair value on a non-recurring basis, in periods subsequent to their initial measurement. The hierarchy requires us to use observable inputs when available and to minimize the use of unobservable inputs when determining fair value. The three tiers are defined as follows: • Level 1. Observable inputs based on unadjusted quoted prices in active markets for identical assets or liabilities; • Level 2. Inputs, other than quoted prices in active markets, that are observable either directly or indirectly; and • Level 3. Unobservable inputs for which there is little or no market data, and which require us to develop our own estimates and assumptions reflecting those that a market participant would use. The asset or liability’s fair value measurement level within the fair value hierarchy is based on the lowest level of any input that is significant to the fair value measurement. Valuation techniques maximize the use of relevant observable inputs and minimize the use of unobservable inputs. There were no instruments measured at fair value on a recurring basis using significant unobservable inputs during the years ended December 31, 2022 and 2021. The valuation techniques that may be used to measure fair value are as follows: 91 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS • Market approach. Uses prices and other relevant information generated by market transactions involving identical or comparable assets or liabilities; • Income approach. Uses valuation techniques to convert future amounts to a single present amount based on current market expectations about those future amounts; and • Cost approach. Based on the amount that currently would be required to replace the service capacity of an asset (i.e., replacement cost). The carrying amounts of our cash and cash equivalents, accounts receivable, accounts payable, and accrued expenses approximate fair value as of December 31, 2022 and 2021 because of the relatively short duration of these instruments. Additionally, the carrying value of our debt associated with the term loan facility approximates fair value because the interest rates are variable and reset on a relatively short durations to the then market rates. Investments Our investment portfolio consists largely of debt investments classified as available-for-sale. Changes in the fair value of available-for-sale securities, excluding other-than-temporary impairments, are recorded in accumulated other comprehensive loss in our consolidated balance sheets. The components of our investments as of December 31, 2022 and 2021 are as follows (in thousands): As of December 31, 2022 Fair Value Measurement Balance Sheet Classification Fair Value Level Cost Basis Unrealized Gains (Losses) Market Value Cash and Cash Equivalents Short-term Investments and Marketable Securities Money market fund Level 1 $ 39,469 $ — $ 39,469 $ 39,469 $ — U.S. Treasury bonds Level 1 9,396 ( 13 ) 9,383 — 9,383 Commercial paper Level 2 26,704 — 26,704 — 26,704 Corporate bonds Level 2 9,353 ( 12 ) 9,341 — 9,341 Agency bonds Level 2 2,432 3 2,435 2,435 Total investments $ 87,354 $ ( 22 ) $ 87,332 $ 39,469 $ 47,863 As of December 31, 2021, our investments consisted of the following (in thousands): As of December 31, 2021 Fair Value Measurement Balance Sheet Classification Fair Value Level Cost Basis Unrealized Gains (Losses) Market Value Cash and Cash Equivalents Short-Term Investments and Marketable Securities Long-Term Investments Money market fund Level 1 $ 38,301 $ — $ 38,301 $ 38,301 $ — $ — U.S. Treasury bonds Level 1 8,171 — 8,171 — 8,171 — Commercial paper Level 2 23,312 — 23,312 — 23,312 — Corporate bonds Level 2 20,107 ( 14 ) 20,093 — 8,049 12,044 Asset-backed securities Level 2 15,655 ( 8 ) 15,647 — 15,647 — Total investments $ 105,546 $ ( 22 ) $ 105,524 $ 38,301 $ 55,179 $ 12,044 92 APPIAN CORPORATION AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS There were no Level 3 assets held at any point during the year ended December 31, 2022 and 2021. Additionally, there were no transfers between Levels 1 and 2 during the years ended December 31, 2022 and 2021. Interest income on our investments totaled $ 0.9 million for the year ended December 31, 2022. The amortized cost basis and fair value of debt securities at December 31, 2022 and 2021, by contractual maturity, are as follows (in thousands): As of December 31, 2022 Cost Basis Fair Value Due in one year or less $ 87,354 $ 87,332 Due after one year through five years — — Total investments $ 87,354 $ 87,332 As of December 31, 2021 Cost Basis Fair Value Due in one year or less $ 93,497 $ 93,480 Due after one year through five years 12,049 12,044 Total investments $ 105,546 $ 105,524 Actual maturities may differ from the contractual maturities in the table above because borrowers have the right to call or prepay certain obligations. 93 Item 9. Changes in and Disagreements with Accountants on Accounting and Financial Disclosure. None.