Upland Software, Inc. 10-K

Item 8. Financial Statements and Supplementary Data UPLAND SOFTWARE, INC. INDEX TO CONSOLIDATED FINANCIAL STATEMENTS Report of Independent Registered Public Accounting Firm (PCAOB ID: 42 ) 57 Consolidated Balance Sheets 60 Consolidated Statements of Operations 62 Consolidated Statements of Comprehensive Loss 63 Consolidated Statements of Equity 64 Consolidated Statements of Cash Flows 65 Notes to Consolidated Financial Statements 66 56 Report of Independent Registered Public Accounting Firm To the Stockholders and the Board of Directors of Upland Software, Inc. Opinion on the Financial Statements We have audited the accompanying consolidated balance sheets of Upland Software, Inc. (the Company) as of December 31, 2022 and 2021, the related consolidated statements of operations, comprehensive loss, 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 U.S. generally accepted accounting principles. 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 issued by the Committee of Sponsoring Organizations of the Treadway Commission (2013 framework) and our report dated February 28, 2023, expressed an unqualified opinion thereon. Basis for Opinion These financial statements are the responsibility of the Company's management. Our responsibility is to express an opinion on the Company’s 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 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 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 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 financial statements. We believe that our audits provide a reasonable basis for our opinion. Critical Audit Matters The critical audit matters communicated below are matters arising from the current period audit of the financial statements that were communicated or required to be communicated to the audit committee and that: (1) relate to accounts or disclosures that are material to the financial statements and (2) involved our especially challenging, subjective or complex judgments. The communication of critical audit matters does not alter in any way our opinion on the consolidated financial statements, taken as a whole, and we are not, by communicating the critical audit matters below, providing separate opinions on the critical audit matters or on the accounts or disclosures to which they relate. Revenue recognition for new products and services Description of the Matter The Company frequently acquires companies that have their own portfolio of products and services that will be included in the Upland suite of offerings. For each of these new products and services, the Company must understand the terms and conditions contained in the contracts with customers and evaluate and apply the five-step model under ASC 606 to ensure proper revenue recognition. Management performs detailed contract review procedures to ensure that any non-standard terms and conditions included in the contracts are properly considered in relation to the accounting literature. 57 Auditing the Company’s revenue recognition analysis related to new products and services, primarily from acquisitions, was challenging due to the effort required in identifying and evaluating non-standard terms and conditions in contracts under Upland’s revenue recognition policy, in accordance with ASC 606. For example, there may be non-standard terms and conditions that required judgment to determine distinct performance obligations, transaction price, or the pattern of revenue recognition. How We Addressed the Matter in Our Audit We obtained an understanding, evaluated the design and tested the operating effectiveness of the Company's internal controls over the process to evaluate the application of the Company’s revenue recognition policy to newly added products and services. This included the controls related to the determination of distinct performance obligations, transaction price, and pattern of revenue recognition. Among other procedures, we obtained and evaluated management’s assessment of the respective revenue recognition for new products and services. We also reviewed management’s evidence for compiling the complete portfolio of contracts and selected a sample of executed contracts to review the terms and conditions. For each of the contracts we reviewed, we identified the promised goods and services in the contract and assessed the distinct performance obligations. We also evaluated the impact of non-standard terms and conditions on the determination of the transaction price and pattern of revenue recognition. Measurement of Income Tax Provision Description of the Matter As more fully described in Notes 2 and 6 to the consolidated financial statements, the Company operates in domestic and international markets and is subject to tax law in the U.S., U.K., and other foreign tax jurisdictions. The income tax provision is an estimate based on management’s understanding of current enacted tax laws and tax rates of each tax jurisdiction. The Company’s accounting for income taxes involves the application of complex and changing tax laws, regulations, and case law in multiple jurisdictions as it relates to non-routine transactions such as acquisitions. The Company utilizes judgment in the interpretation of tax laws, regulations, and case law as they apply to its tax positions. For the year ended December 31, 2022, income tax benefit was $1.7 million. Auditing management’s calculation of the provision for income taxes was complex because the provision for income taxes involved auditor judgment, due to the interpretation of tax laws, regulations, and case law across multiple jurisdictions, the application of those laws, regulations, and case law as it relates to non-routine transactions such as acquisitions, and evaluation of the application of such tax laws, regulations, and case law to the Company’s tax positions. These matters are subject to legal and factual interpretation. Our audit procedures required significant audit effort, including the use of our tax professionals to assist in evaluating the audit evidence obtained from our procedures. How We Addressed the Matter in Our Audit We obtained an understanding, evaluated the design and tested the operating effectiveness of internal controls relating to the provision for income taxes, inclusive of management’s review of the provision for income taxes and interpretation of tax laws, regulations, and case law. For example, we tested the Company’s controls over management’s review of the underlying data used in the provision for income tax calculations and controls over management’s review of the analysis provided by advisors utilized in the application of tax law to the Company’s tax positions. Among other audit procedures performed, we assessed the Company’s evaluation of tax laws, regulations, and case law, and tested the provision for income tax calculations including the completeness and accuracy of underlying data used in the calculations. We involved our tax matter professionals to evaluate the Company’s interpretation and application of tax laws, regulations, and case law to the Company’s tax positions. This included evaluating advice obtained by the Company. We have also evaluated the Company’s income tax disclosures included in Notes 2 and 6 of the consolidated financial statements in relation to these matters. Evaluation of goodwill for impairment Description of the Matter At December 31, 2022, the Company’s goodwill balance was $477 million. As discussed in Note 1 to the consolidated financial statements, goodwill is tested at least annually for impairment and more frequently when indicators of impairment are identified. Estimating fair values in connection with this impairment evaluation involves the utilization of the discounted cash flow and guideline public company approaches. As described in Note 5 to the consolidated financial statements, the Company recorded a goodwill impairment charge of $12.5 million during the year ended December 31, 2022. 58 Auditing management’s goodwill impairment assessment was complex and required auditor judgment because the estimation of fair values involves subjective management assumptions, including estimation of future cash flows, the long-term rate of growth for the Company’s business and weighted average cost of capital. Assumptions used in these valuation models are forward-looking, and changes in these assumptions can have a material effect on the determination of fair value. How We Addressed the Matter in Our Audit We obtained an understanding, evaluated the design, and tested the operating effectiveness of certain controls over the Company’s impairment assessment process, including controls over management’s review of the valuation models and its determination of the significant assumptions described above. To test the Company’s impairment evaluation, our audit procedures included, among others, assessing the valuation methodologies and testing the significant assumptions discussed above and the underlying data used by the Company in its evaluation. For example, we compared the significant assumptions to current industry, market, and economic trends, to historical results of the Company and to other guideline companies within the same industry. We also performed independent sensitivity analyses to evaluate the changes in the fair value of the reporting unit that would result from changes in the significant assumptions. We involved our valuation specialists to assist in evaluating the methodologies and auditing the significant assumptions used to calculate the estimated fair values. /s/ Ernst & Young LLP We have served as the Company’s auditor since 2013. Austin, Texas February 28, 2023 59 Upland Software, Inc. Consolidated Balance Sheets (in thousands, except share and per share amounts) December 31, 2022 2021 ASSETS Current assets: Cash and cash equivalents $ 248,653 $ 189,158 Accounts receivable, net of allowance for credit losses 47,594 50,499 Deferred commissions, current 10,961 9,824 Unbilled receivables 5,313 4,801 Prepaid expenses and other current assets 8,774 8,709 Total current assets 321,295 262,991 Tax credits receivable 2,411 3,345 Property and equipment, net 1,830 2,667 Operating lease right-of-use asset 5,719 6,454 Intangible assets, net 248,851 279,920 Goodwill 477,043 457,472 Deferred commissions, noncurrent 13,794 14,808 Interest rate swap assets 41,168 — Other assets 1,348 1,350 Total assets $ 1,113,459 $ 1,029,007 60 (in thousands, except share and per share amounts) December 31, 2022 2021 LIABILITIES, CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS' EQUITY Current liabilities: Accounts payable $ 14,939 $ 20,362 Accrued compensation 7,393 9,829 Accrued expenses and other current liabilities 10,644 9,086 Deferred revenue 106,465 102,847 Liabilities due to sellers of businesses 5,429 7,607 Operating lease liabilities, current 3,205 3,546 Current maturities of notes payable (includes unamortized discount of $ 2,264 and $ 2,233 at December 31, 2022 and December 31, 2021, respectively) 3,136 3,167 Total current liabilities 151,211 156,444 Notes payable, less current maturities (includes unamortized discount of $ 5,203 and $ 7,287 at December 31, 2022 and December 31, 2021, respectively) 511,847 515,163 Deferred revenue, noncurrent 4,707 2,058 Operating lease liabilities, noncurrent 4,947 6,773 Noncurrent deferred tax liability, net 18,416 22,793 Interest rate swap liabilities — 8,409 Other long-term liabilities 1,170 1,079 Total liabilities 692,298 712,719 Series A Convertible Preferred stock, 0.0001 par value; 5,000,000 shares authorized: 115,000 shares issued and outstanding as of December 31, 2022; no shares issued and outstanding as of December 31, 2021, respectively. 112,291 — Stockholders’ equity: Common stock, $ 0.0001 par value; 50,000,000 shares authorized: 32,221,855 and 31,096,548 shares issued and outstanding as of December 31, 2022 and December 31, 2021, respectively) 3 3 Additional paid-in capital 606,755 568,384 Accumulated other comprehensive income (loss) 11,110 ( 11,514 ) Accumulated deficit ( 308,998 ) ( 240,585 ) Total stockholders’ equity 308,870 316,288 Total liabilities, convertible preferred stock and stockholders’ equity $ 1,113,459 $ 1,029,007 See accompanying notes. 61 Upland Software, Inc. Consolidated Statements of Operations (in thousands, except share and per share amounts) Year Ended December 31, 2022 2021 2020 Revenue: Subscription and support $ 297,887 $ 287,621 $ 277,504 Perpetual license 6,948 2,150 1,884 Total product revenue 304,835 289,771 279,388 Professional services 12,468 12,245 12,390 Total revenue 317,303 302,016 291,778 Cost of revenue: Subscription and support 93,948 92,168 89,880 Professional services 9,793 7,285 8,566 Total cost of revenue 103,741 99,453 98,446 Gross profit 213,562 202,563 193,332 Operating expenses: Sales and marketing 59,416 55,097 46,077 Research and development 46,187 42,693 39,002 General and administrative 70,462 76,901 68,072 Depreciation and amortization 43,669 41,315 36,919 Acquisition-related expenses 21,556 21,234 27,075 Impairment of goodwill 12,500 — — Total operating expenses 253,790 237,240 217,145 Loss from operations ( 40,228 ) ( 34,677 ) ( 23,813 ) Other expense: Interest expense, net ( 29,145 ) ( 31,626 ) ( 31,529 ) Other expense, net ( 781 ) ( 253 ) ( 111 ) Total other expense ( 29,926 ) ( 31,879 ) ( 31,640 ) Loss before benefit from income taxes ( 70,154 ) ( 66,556 ) ( 55,453 ) Benefit from income taxes 1,741 8,344 4,234 Net loss $ ( 68,413 ) $ ( 58,212 ) $ ( 51,219 ) Preferred stock dividends ( 1,846 ) — — Net loss attributable to common shareholders $ ( 70,259 ) $ ( 58,212 ) $ ( 51,219 ) Net loss per common share: Net loss per common share, basic and diluted $ ( 2.23 ) $ ( 1.92 ) $ ( 1.92 ) Weighted-average common shares outstanding, basic and diluted 31,528,881 30,295,769 26,632,116 See accompanying notes. 62 Upland Software, Inc. Consolidated Statements of Comprehensive Loss (in thousands) Year Ended December 31, 2022 2021 2020 Net loss $ ( 68,413 ) $ ( 58,212 ) $ ( 51,219 ) Other comprehensive income (loss): Foreign currency gain (loss) translation adjustment ( 16,975 ) ( 6,301 ) 5,173 Unrealized translation gain (loss) on intercompany loans with foreign subsidiaries ( 9,978 ) ( 602 ) 2,271 Unrealized gain (loss) on interest rate swaps 49,577 21,623 ( 32,455 ) Other comprehensive income (loss): $ 22,624 $ 14,720 $ ( 25,011 ) Comprehensive loss $ ( 45,789 ) $ ( 43,492 ) $ ( 76,230 ) See accompanying notes. 63 Upland Software, Inc. Consolidated Statements of Equity ( in thousands, except share amount ) Preferred Stock Common Stock Additional Paid-In Capital Accumulated Other Comprehensive Income (Loss) Accumulated Deficit Total Stockholders’ Equity Shares Amount Shares Amount Balance at December 31, 2019 — — 25,250,120 $ 3 $ 345,127 $ ( 1,223 ) $ ( 131,046 ) $ 212,861 Issuance of stock under Company plans, net of shares withheld for tax — — 711,994 — ( 1,673 ) — — ( 1,673 ) Issuance of stock, net of issuance costs — — 4,025,000 — 130,073 — — 130,073 Stock-based compensation — — — — 41,692 — — 41,692 Cumulative adjustment related to adoption of accounting standard — — — — — — ( 108 ) ( 108 ) Foreign currency translation adjustment — — — — — 5,173 — 5,173 Unrealized translation gain on foreign currency denominated intercompany loans — — — — — 2,271 — 2,271 Unrealized loss on interest rate swaps — — — — — ( 32,455 ) — ( 32,455 ) Net loss — — — — — — ( 51,219 ) ( 51,219 ) Balance at December 31, 2020 — $ — 29,987,114 $ 3 $ 515,219 $ ( 26,234 ) $ ( 182,373 ) $ 306,615 Issuance of stock under Company plans, net of shares withheld for tax — — 1,109,434 — ( 708 ) — — ( 708 ) Stock-based compensation — — — — 53,873 — — 53,873 Foreign currency translation adjustment — — — — — ( 6,301 ) — ( 6,301 ) Unrealized translation loss on intercompany loans with foreign subsidiaries — — — — — ( 602 ) — ( 602 ) Unrealized gain on interest rate swaps — — — — — 21,623 — 21,623 Net loss — — — — — — ( 58,212 ) ( 58,212 ) Balance at December 31, 2021 — $ — 31,096,548 $ 3 $ 568,384 $ ( 11,514 ) $ ( 240,585 ) $ 316,288 Issuance of Convertible Preferred Stock 115,000 110,445 — — — — — — Dividends accrued - Convertible Preferred Stock — 1,846 — — ( 1,846 ) — — ( 1,846 ) Issuance of stock under Company plans, net of shares withheld for tax — — 1,125,307 — ( 1,385 ) — — ( 1,385 ) Stock-based compensation — — — — 41,602 — — 41,602 Foreign currency translation adjustment — — — — — ( 16,975 ) — ( 16,975 ) Unrealized translation loss on intercompany loans with foreign subsidiaries — — — — — ( 9,978 ) — ( 9,978 ) Unrealized gain on interest rate swaps — — — — — 49,577 — 49,577 Net loss — — — — — — ( 68,413 ) ( 68,413 ) Balance at December 31, 2022 115,000 $ 112,291 32,221,855 $ 3 $ 606,755 $ 11,110 $ ( 308,998 ) $ 308,870 See accompanying notes. 64 Upland Software, Inc. Consolidated Statements of Cash Flows (in thousands) Year Ended December 31, 2022 2021 2020 Operating activities Net loss $ ( 68,413 ) $ ( 58,212 ) $ ( 51,219 ) Adjustments to reconcile net loss to net cash provided by operating activities: Depreciation and amortization 56,146 52,928 47,164 Change in fair value of liabilities due to sellers of businesses ( 75 ) ( 4,510 ) ( 340 ) Deferred income taxes ( 7,075 ) ( 11,179 ) ( 7,533 ) Amortization of deferred costs 12,198 8,948 4,684 Foreign currency re-measurement loss ( 12 ) 25 272 Non-cash interest and other expense 2,256 2,249 2,233 Non-cash stock compensation expense 41,602 53,873 41,692 Non-cash loss on impairment of goodwill 12,500 — — Non-cash loss on retirement of fixed assets 79 — 635 Changes in operating assets and liabilities, net of purchase business combinations: Accounts receivable 9,691 ( 1,665 ) 10,355 Prepaid expenses and other current assets ( 2,741 ) ( 7,499 ) ( 8,582 ) Accounts payable ( 7,175 ) 10,865 ( 3,081 ) Accrued expenses and other liabilities ( 14,013 ) ( 9,660 ) ( 7,485 ) Deferred revenue ( 4,989 ) 5,575 6,825 Net cash provided by operating activities 29,979 41,738 35,620 Investing activities Purchase of property and equipment ( 866 ) ( 1,115 ) ( 1,114 ) Purchase of customer relationships — — ( 201 ) Purchase business combinations, net of cash acquired ( 62,356 ) ( 92,417 ) ( 67,655 ) Net cash used in investing activities ( 63,222 ) ( 93,532 ) ( 68,970 ) Financing activities Payments on finance leases — ( 12 ) ( 88 ) Proceeds from notes payable, net of issuance costs ( 203 ) ( 122 ) ( 303 ) Payments on notes payable ( 5,400 ) ( 5,400 ) ( 5,400 ) Issuance of Series A Convertible Preferred stock, net of issuance costs 110,445 — — Taxes paid related to net share settlement of equity awards ( 1,576 ) ( 982 ) ( 2,139 ) Issuance of common stock, net of issuance costs 191 274 130,539 Additional consideration paid to sellers of businesses ( 9,306 ) ( 1,938 ) ( 14,710 ) Net cash provided by (used in) financing activities 94,151 ( 8,180 ) 107,899 Effect of exchange rate fluctuations on cash ( 1,413 ) ( 897 ) 456 Change in cash and cash equivalents 59,495 ( 60,871 ) 75,005 Cash and cash equivalents, beginning of period 189,158 250,029 175,024 Cash and cash equivalents, end of period $ 248,653 $ 189,158 $ 250,029 Supplemental disclosures of cash flow information: Cash paid for interest, net of interest rate swaps $ 29,120 $ 29,427 $ 29,919 Cash paid for taxes $ 3,876 $ 2,846 $ 3,185 Non-cash investing and financing activities: Business combination consideration including holdbacks and earnouts $ 8,126 $ 11,670 $ ( 4,893 ) See accompanying notes. 65 Upland Software, Inc. Notes to Consolidated Financial Statements 1. Organization and Nature of Operations Upland Software, Inc. (“Upland,” “we,” “us,” “our,” or the “Company”), a Delaware corporation, is a provider of cloud-based software that enables organizations to plan, manage and execute projects and work. Upland’s cloud offerings address a broad range of software needs, from strategic planning to task execution in the following functional areas: Sales, Marketing, Contact Center, Knowledge Management, Project Management, Information Technology, Business Operations, and Human Resources and Legal. To support continued growth, Upland intends to pursue acquisitions within its cloud offerings of complementary technologies and businesses. Upland expects that this will expand its product offerings, customer base and market access, resulting in increased benefits of scale. Consistent with Upland’s growth strategy, Upland has made a total of 31 acquisitions in the 11 years ending December 31, 2022. 2. Basis of Presentation and Summary of Significant Accounting Policies Basis of Presentation These consolidated financial statements have been prepared in conformity with accounting principles generally accepted in the United States (“GAAP”). The consolidated financial statements include the accounts of the Company and its wholly owned subsidiaries. All intercompany accounts and transactions have been eliminated in consolidation. There have been no significant changes in the Company’s accounting policies since December 31, 2021. Use of Estimates The preparation of the accompanying consolidated financial statements in conformity with GAAP requires management to make, on an ongoing basis, estimates and assumptions that affect the reported amounts of assets and liabilities, disclosure of contingent assets and liabilities at the date of the consolidated financial statements, and the reported amounts of revenues and expenses. Significant items subject to such estimates include those related to revenue recognition, deferred commissions, allowance for credit losses, stock-based compensation, contingent consideration, acquired intangible assets, the useful lives of intangible assets and property and equipment, and income taxes. In accordance with GAAP, management bases its estimates on historical experience and on various other assumptions that management believes are reasonable under the circumstances. Management regularly evaluates its estimates and assumptions using historical experience and other factors; however, actual results could differ from those estimates. Upland is not aware of any specific event or circumstance that would require an update to its estimates or judgments or a revision of the carrying value of its assets or liabilities as of February 28, 2023, the date of issuance of this Annual Report on Form 10-K. These estimates may change as new events occur and additional information is obtained. Actual results could differ materially from these estimates under different assumptions or conditions. Cash and Cash Equivalents Cash and cash equivalents consist of cash deposits and liquid investments with original maturities of three months or less when purchased. Cash equivalents are stated at cost, which approximates market value, because of the short maturity of these instruments. Accounts Receivable and Allowance for Credit Losses On January 1, 2020, the Company adopted ASU 2016-13, Financial Instruments - Credit Losses: Measurement of Credit Losses on Financial Instruments . The adoption of ASU 2016-13 resulted in recording a cumulative-effect adjustment to decrease the beginning balance (at January 1, 2020) of Accumulated deficit in the amount of $ 0.1 million, which represented the accelerated recognition of credit losses related to our trade receivables under the expected credit loss model of calculating our current expected credit losses compared to the previous incurred loss model. The Company extends credit to the majority of its customers. Issuance of credit is based on ongoing credit evaluations by the Company of customers’ financial condition and generally requires no collateral. Trade accounts receivable are recorded at the invoiced amount and do not bear interest. Invoices generally require payment due upon receipt of invoice. The Company 66 generally does not charge interest on past due payments, although the Company's contracts with its customers usually allow it to do so. To manage accounts receivable credit risk, the Company performs periodic credit evaluations of its customers and maintains current expected credit losses which considers such factors as historical loss information, geographic location of customers, current market conditions, and reasonable and supportable forecasts. The following table presents the changes in the allowance for credit losses (in thousands): Year Ended December 31, 2022 2021 2020 Balance at beginning of year $ 1,107 $ 1,465 $ 1,238 Cumulative adjustment related to adoption of ASU 2016-13 — — 108 Provision for credit losses 556 694 1,115 Writeoffs, net of recoveries and other ( 505 ) ( 1,052 ) ( 996 ) Balance at end of year $ 1,158 $ 1,107 $ 1,465 Concentration of Credit Risk and Significant Customers Financial instruments that potentially subject the Company to credit risk consist of cash and cash equivalents and accounts receivable. The Company’s cash and cash equivalents are placed with high-quality financial institutions, which, at times, may exceed federally insured limits. The Company has not experienced any losses in these accounts, and the Company does not believe it is exposed to any significant credit risk related to cash and cash equivalents. The Company provides credit, in the normal course of business, to a number of its customers. The Company performs periodic credit evaluations of its customers and generally does not require collateral. No individual customer represented more than 10% of total revenues or more than 10% of accounts receivable in the years ended December 31, 2022, 2021 or 2020. Property and Equipment Property and equipment are carried at cost, less accumulated depreciation and amortization. Depreciation of property and equipment is computed using the straight-line method over each asset’s useful life. Leasehold improvements are amortized over the shorter of the lease term or of the estimated useful lives of the related assets. Upon retirement or disposal, the cost of each asset and the related accumulated depreciation are removed from the accounts and any resulting gain or loss is credited or charged to income. Repairs, maintenance, and minor replacements are expensed as incurred. The estimated useful lives of property and equipment are as follows: Computer hardware and equipment 3 - 5 years Purchased software and licenses 3 - 5 years Furniture and fixtures 7 years Leasehold improvements Lesser of estimated useful life or lease term Business Combinations We apply the provisions of Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”) 805, Business Combinations , in accounting for our acquisitions which requires the acquisition purchase price to be allocated to the tangible and intangible assets acquired and liabilities assumed based on their estimated fair values at the acquisition dates. The excess of the purchase price over these estimated fair values is recorded to goodwill. Significant estimates and assumptions, including fair value estimates, are used to determine the fair value of assets acquired, liabilities assumed, and contingent consideration transferred as well as the useful lives of long-lived assets acquired. During the measurement period, which may be up to one year from the acquisition date, we may record adjustments to the assets acquired and liabilities assumed with the corresponding offset to goodwill based on changes to our initial estimates and assumptions. Upon conclusion of the measurement period or final determination of the values of assets acquired and liabilities assumed, whichever comes first, any subsequent adjustments are recorded to Acquisition-related expenses on our consolidated statement of operations. 67 Tangible assets are valued at their respective carrying amounts, which approximates their estimated fair value. The valuation of identifiable intangible assets reflects management’s estimates based on, among other factors, use of established valuation methods. Customer relationships are valued using the multi-period excess earnings method income approach, which estimates fair value based on the earnings and cash flow capacity of the subject asset. Developed technology and trade names are valued using the relief-from-royalty method, which estimates fair value based on the value the owner of the asset receives from not having to pay a royalty to use the asset. The purchase price transferred in our acquisitions often contain holdback and contingent consideration provisions. Holdbacks are subject to reduction for indemnification claims and are typically payable within 12 to 18 months of the acquisition date and are recorded in Liabilities due to sellers of businesses on our consolidated balance sheets. Contingent consideration typically includes earnout payments payable within 6 to 18 months of the date of acquisition based on attainment of certain performance goals. Contingent consideration liabilities are recorded at fair value on the acquisition date and are remeasured periodically based on the then assessed fair value and adjusted, if necessary. Holdback and contingent consideration liabilities are recorded in Liabilities due to sellers of businesses on our consolidated balance sheet based on their estimated fair values. The estimated fair value of contingent consideration related to potential earnout payments is calculated utilizing a binary option model, and this amount is recorded in Liabilities due to sellers of businesses on our consolidated balance sheets. The fair value of contingent consideration is estimated on a quarterly basis through a collaborative effort by our sales and finance departments. Changes in the fair value of contingent consideration subsequent to the purchase price finalization are recorded as Acquisition-related expenses or Other income (expense), net on our consolidated statements of operations based on management’s assessment of the nature of the liability. In the event a holdback is reduced subsequent to the finalization of purchase accounting, the reduction is recorded as a gain in Acquisition-related expenses or Other income (expense), net on our consolidated statements of operations based on management’s assessment of the nature of the liability. Goodwill and Other Intangibles We assess Goodwill for impairment annually on October 1st, or more frequently when an event occurs which could cause the Carrying Value (or GAAP basis book value) of our Company to exceed the estimated fair value of our Company. The Company adopted ASU 2017-04, Intangibles - Goodwill and Other: Simplifying the Test for Goodwill Impairment during the first quarter of 2018. As we operate as one reporting unit, the Goodwill impairment evaluation is performed at the consolidated entity level by comparing the estimated fair value of the Company to its Carrying Value. We first assess qualitative factors to determine whether it is more likely than not that the fair value of our single reporting unit is less than its Carrying Value. Based on the qualitative assessment, if it is determined that it is more likely than not that the Company's fair value is less than its Carrying Value, then we perform a quantitative analysis using a fair-value-based approach to determine if the fair value of our reporting unit is less than its Carrying Value. See “ Note 5. Goodwill and Other Intangible Assets” f or more information regarding our fourth quarter 2022 Goodwill impairment. Identifiable intangible assets consist of customer relationships, marketing-related intangible assets and developed technology. Intangible assets with definite lives are amortized over their estimated useful lives on a straight-line basis. The straight-line method of amortization represents the Company’s best estimate of the distribution of the economic value of the identifiable intangible assets. Intangible assets are reviewed for impairment whenever events or changes in circumstances indicate the carrying amount of intangible assets may not be recoverable. Conditions that would necessitate an impairment assessment include a significant decline in the observable market value of an asset, a significant change in the extent or manner in which an asset is used or any other significant adverse change that would indicate that the carrying amount of an asset or group of assets may not be recoverable. The Company evaluates the recoverability of intangible assets by comparing their carrying amounts to the future net undiscounted cash flows expected to be generated by the intangible assets. If such intangible assets are considered to be impaired, the impairment to be recognized is measured as the amount by which the carrying amount of the intangible assets exceeds the fair value of the assets. Long-Lived Assets Long-lived assets are reviewed for impairment whenever events or circumstances indicate their carrying value may not be recoverable. When such events or circumstances arise, an estimate of future undiscounted cash flows produced by the asset, or the appropriate grouping of assets, is compared to the asset's carrying value to determine whether impairment exists. If the asset is determined to be impaired, the impairment loss is measured based on the excess of its carrying value over its fair value. Assets to be disposed of are reported at the lower of the carrying value or net realizable value. No indicators of impairment were identified during the years ended December 31, 2022, 2021 or 2020. 68 Software Development Costs Software development costs are expensed as incurred until the point the Company establishes technological feasibility. Technological feasibility is established upon the completion of a working model. Costs incurred by the Company between establishment of technological feasibility and the point at which the product is ready for general release are capitalized, subject to their recoverability, and amortized over the economic life of the related products. Because the Company believes its current process for developing its software products essentially results in the completion of a working product concurrent with the establishment of technological feasibility, no software development costs have been capitalized to date. There were no software development costs required to be capitalized under ASC 985-20, Costs of Software to be Sold, Leased or Marketed . Software development costs associated with internal use software are incurred in three stages of development: the preliminary project stage, the application development stage, and the post-implementation stage. Costs incurred during the preliminary project and post-implementation stages are expensed as incurred. Eligible internal and external costs associated with significant upgrades and enhancements incurred during the application development stage are capitalized as property and equipment. During the years ended December 31, 2022, 2021 or 2020, there were no internal use software development costs capitalized under ASC 350-40, Internal-Use Software . ASC 350-40 also requires hosting arrangements that are service contracts to follow the guidance for internal-use software to determine which implementation costs can be capitalized. In accordance with ASC 350-40, (i) capitalized implementation costs are classified in the same balance sheet line item as the amounts prepaid for the related hosting arrangement; (ii) amortization of capitalized implementation costs are presented in the same income statement line item as the service fees for the related hosting arrangement; and (iii) cash flows related to capitalized implementation costs are presented within the same category of cash flow activity as the cash flows for the related hosting arrangement (i.e. operating activity). As of December 31, 2022 and 2021, the net carrying value of capitalized implementation costs related to hosting arrangements that were incurred during the application development stage were $ 0.1 million and $ 0.3 million, respectively. These costs related primarily to the implementation of a new ERP system. These capitalized implementation costs will be amortized over the expected term of the arrangement and are amortized in the same line item on our consolidated statements of operations as the expense for fees for the associated hosting arrangement. Debt Issuance Costs The Company capitalizes underwriting, legal, and other direct costs incurred related to the issuance of debt, which are recorded as a direct deduction from the carrying amount of the related debt liability and amortized to interest expense, net over the term of the related debt using the effective interest rate method. Upon the extinguishment of the related debt, any unamortized capitalized debt issuance costs are recorded to Interest expense, net on our consolidated statement of operations. In 2022 and 2021, the Company had no write offs of debt issuance costs. Derivatives The Company entered into floating-to-fixed interest rate swap agreements to limit exposure to interest rate risk related to our debt. These interest rate swaps effectively converted the entire balance of the Company's $ 540 million original principal term loans from variable interest payments to fixed interest rate payments, based on an annualized fixed rate of 5.4 %, for the 7 year term of the debt. ASC 815, Derivatives and Hedging , requires entities to recognize derivative instruments as either assets or liabilities in the statement of financial position at fair value. The accounting for changes in the fair value (i.e., gains or losses) of a derivative instrument depends on whether it has been designated and qualifies as part of a hedging relationship and, further, on the type of hedging relationship. The Company assessed the effectiveness of the hedging relationship under the hypothetical derivative method and noted that all of the critical terms of the hypothetical derivative and hedging instrument were the same. The hedging relationship continues to limit the Company’s exposure to the variability in interest rates under the Company’s term loans and related cash outflows. As such, the Company has deemed this hedging relationship as highly effective in offsetting cash flows attributable to hedged risk (variability in forecasted monthly interest payments) for the term of the term loans and interest rate swap agreements. All derivative financial instruments are recorded at fair value as a net asset or liability on our consolidated balance sheets. As of December 31, 2022, the fair value of interest rate swaps included in Interest rate swap assets on our consolidated balance sheets was $ 41.2 million. As of December 31, 2021, the fair value of interest rate swaps included in Interest rate swap liabilities was $ 8.4 million. The change in the fair value of the hedging instruments is recorded in Unrealized gain (loss) on interest rate swaps on our consolidated stateme nts of comprehensive income. Amounts deferred in Unrealized gain (loss) on interest rate swaps in our consolidated statements of comprehensive income will be reclassified to Interest expense, net on our consolidated statements of operations in the period in which the hedged item affects earnings. 69 Fair Value of Financial Instruments The Company recognizes financial instruments in accordance with the authoritative guidance on fair value measurements and disclosures for financial assets and liabilities. This guidance defines fair value, establishes a framework for measuring fair value in accordance with GAAP, and expands disclosures about fair value measurements. The guidance also establishes a three-tier fair value hierarchy, which prioritizes the inputs used in measuring fair value. These tiers include Level 1, defined as observable inputs, such as quoted prices in active markets; Level 2, defined as inputs other than quoted prices in active markets that are either directly or indirectly observable; and Level 3, defined as unobservable inputs in which little or no market data exists, therefore, requiring an entity to develop its own assumptions. The Company adopted ASU 2018-13, Fair Value Measurement (Topic 820): Disclosure Framework — Changes to the Disclosure Requirements for Fair Value Measurement , in the first quarter of 2020. Under ASU 2018-13, entities will no longer be required to disclose the amount of and reasons for transfers between Level 1 and Level 2 of the fair value hierarchy, but public business entities will be required to disclose the range and weighted average used to develop significant unobservable inputs for Level 3 fair value measurements. The Company’s financial instruments consist principally of cash and cash equivalents, accounts receivable, accounts payable, and long–term debt. The carrying value of cash and cash equivalents, accounts receivable, and accounts payable approximate fair value, primarily due to short maturities. The carrying values of the Company’s debt instruments approximated their fair value based on rates currently available to the Company. Preferred Stock In August 2022, the Company closed on the issuance and sale of its Series A Convertible Preferred Stock (the “Series A Preferred Stock”). The Company issued 115,000 shares of Series A Preferred Stock, par value $ 0.0001 per share, at a price of $ 1,000 per share, for an initial investment amount of $ 115.0 million. Pursuant to the Certification of Designation, cumulative preferred dividends accrue quarterly on the Series A Preferred Stock at a rate of (i) 4.5 % per annum until but excluding the seven year anniversary of the closing, and (ii) 7 % per annum on and after the seven year anniversary of the closing . See “ Note 12. Series A Preferred Stock—Series A Convertible Preferred Stock” for further details. The Series A Preferred Stock and cumulative preferred dividends, net of preferred issuance costs, is presented as Mezzanine Equity of $ 112.3 million as of December 31, 2022 in the Company’s consolidated balance sheets. The Series A Preferred Stock is classified as Mezzanine Equity because it is redeemable at the option of its holders (upon a deemed liquidation event as defined in “ Note 12. Series A Preferred Stock—Series A Convertible Preferred Stock—Deemed Liquidation Event Redemption” ) and has a condition for redemption that is not solely within the control of the issuer. Revenue Recognition Refer to “ Note 14 Revenue Recognition ” for a detailed discussion of accounting policies related to revenue recognition, including deferred revenue and deferred commissions. Cost of Revenue Cost of revenue primarily consists of salaries and related expenses (e.g. bonuses, employee benefits, and payroll taxes) for personnel directly involved in the delivery of services and products directly to customers. Cost of revenue also includes the amortization of acquired technology, and hosting and infrastructure costs related to the delivery of the Company’s products and services. Customer Relationship Acquisition Costs Costs associated with the acquisition or origination of customer relationships are capitalized as customer relationship assets as incurred and amortized over the estimated life of the customer relationship. Refer to “ Note 14. Revenue Recognition ” for further discussion regarding deferred commissions. 70 Advertising Costs Advertising costs are expensed in the period incurred. Advertising expenses were $ 0.8 million, $ 0.9 million and $ 0.1 million for the years ended December 31, 2022, 2021 or 2020, respectively. Advertising costs are recorded in Sales and marketing expenses on our consolidated statement of operations. Income Taxes The Company uses the asset and liability method of accounting for income taxes. Under this method, deferred tax assets and liabilities are recognized for the expected future tax consequences of temporary differences between the carrying amounts and the tax bases of assets and liabilities. Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which those temporary differences are expected to be recovered or settled. The effect of a change in tax rates on deferred tax assets and liabilities will be recognized in the period that includes the enactment date. A valuation allowance is established against the deferred tax assets to reduce their carrying value to an amount that is more likely than not to be realized. The Company has adopted a permanent reinvestment position whereby foreign earnings for foreign subsidiaries are expected to be reinvested and future earnings are not expected to be repatriated. As a result of this policy, no tax liability has been accrued in anticipation of future dividends from foreign subsidiaries. The Company accounts for uncertainty of income taxes based on a “more likely than not” threshold for the recognition and derecognition of tax positions. Interest and penalties are recorded as a component of income tax expense. Leases The Company determines if an arrangement is a lease at inception. This determination includes the review of contracts with third parties to identify the existence of potential embedded leases. Operating leases are included in operating lease right-of-use (“ROU”) assets, current and noncurrent operating lease liabilities on the Company’s consolidated balance sheets. Finance leases are included in property and equipment, accrued expenses and other liabilities, and other noncurrent liabilities on the Company’s consolidated balance sheets. ROU assets represent the Company's right to use an underlying asset for the lease term and the corresponding lease liabilities represent its obligation to make lease payments arising from the lease. Lease ROU assets and lease liabilities are recognized based on the present value of the future minimum lease payments over the lease term at commencement date. The lease ROU asset includes any initial direct costs incurred and is reduced for any tenant incentives. As the Company’s leases do not provide an implicit rate, the net present value of future minimum lease payments is determined using the Company’s incremental borrowing rate. The Company’s lease terms may include options to extend or terminate the lease when it is reasonably certain the Company will exercise that option. Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term. Stock-Based Compensation We measure all share-based payments, including grants of options to purchase common stock and the issuance of restricted stock or restricted stock units to employees, service providers and board members, using the fair-value at grant date. We record forfeitures as they occur. The cost of services received from employees and non-employees in exchange for awards of equity instruments is recognized on our consolidated statement of operations based on the estimated fair value of those awards on the grant date and amortized on a straight-line basis over the requisite service period. We value restricted stock and restricted stock units at the closing price of our common stock on the grant date. We value stock option awards using the Black-Scholes option-pricing model. For the years ended December 31, 2022, 2021 and 2020, stock-based compensation awards consisted primarily of restricted stock and restricted stock units. From time to time, we grant restricted stock units that also include performance or market-based conditions (“PRSUs”). For PRSUs granted with a market condition, we use a Monte Carlo simulation analysis to value the award. Compensation expense for awards with marked-based conditions is recognized over the required service period of the grant based on the grant date fair value of the award and is not subject to fluctuation due to achievement of the underlying market-based condition. 71 Significant assumptions used in the Monte Carlo simulation model for the PRSUs granted during the year ended December 31, 2022 and 2021 are as follows. Year Ended December 31, 2022 2021 Expected volatility 49.5 % 53.6 % Risk-free interest rate 0.7 % 0.1 % Remaining performance period (in years) 1.46 1.35 Dividend yield — — Comprehensive Loss The Company utilizes the guidance in ASC 220, Income Statement—Reporting Comprehensive Income , for the reporting and display of comprehensive loss and its components in the consolidated financial statements. Comprehensive loss consists of net loss, foreign currency translation adjustments for subsidiaries with functional currencies other than the United States dollar (“USD”), unrealized translation gains (losses) on foreign currency denominated intercompany loans, and unrealized gains (losses) on interest rate swaps. Refer to “ Note 13. Stockholders' Equity —Accumulated Other Comprehensive Income (Loss)” for further discussion of the components of accumulated other comprehensive income (loss) for the years ended December 31, 2022, 2021 or 2020. Foreign Currency Transactions The functional currency of our foreign subsidiaries are generally the local currencies. Results of operations for foreign subsidiaries are translated into USD using the average exchange rates on a monthly basis during the year. The assets and liabilities of those subsidiaries are translated into USD using the exchange rates in effect at the balance sheet date. The related translation adjustments are recorded as a separate component of the Company’s consolidated statements of stockholders' equity in accumulated other comprehensive income (loss). Assets and liabilities denominated in currencies other than the functional currency are remeasured using the current exchange rate for monetary accounts and historical exchange rates for non-monetary accounts, with exchange differences on remeasurement included in other expense, net in the accompanying statements of operations. For the year ended December 31, 2022, net losses related to remeasurement of foreign currency transactions of $ 1.0 million were recorded in Other expense, net on our consolidated statements of operations. For the years ended December 31, 2021 and 2020, net gains of $ 48.6 thousand and $ 0.2 million, respectively, were recorded in Other expense, net on our consolidated statements of operations. We have foreign currency denominated intercompany loans that were used to fund the acquisition of foreign subsidiaries. Due to the long-term nature of the loans, the foreign currency gains (losses) resulting from remeasurement are recognized as a separate component of the Company’s consolidated statements of stockholders' equity in accumulated other comprehensive loss. During the year ended December 31, 2020, the balances of these intercompany loans were converted to USD. During the years ended December 31, 2022, 2021 and 2020, a translation loss of $ 10.0 million, loss of $ 0.6 million, and gain of $ 2.3 million, respectively, were recognized as a component of accumulated other comprehensive loss in the Company’s statements of stockholders’ equity, related to long-term intercompany loans. 72 Recent Accounting Pronouncements Recently issued accounting pronouncements - Adopted In August 2020, the Financial Standards Accounting Board (“FASB”) issued accounting standards update ASU 2020-06, “Debt—Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging—Contracts in Entity’s Own Equity (Subtopic 815-40): Accounting for Convertible Instruments and Contracts in an Entity’s Own Equity (the “ASU 2020-06). ASU 2020-06 simplifies the accounting for convertible instruments by reducing the number of accounting models available for convertible debt instruments and convertible preferred stock. This update also amends the guidance for the derivatives scope exception for contracts in an entity’s own equity to reduce form-over-substance-based accounting conclusions. ASU 2020-06 amends the diluted earnings per share guidance, including the requirement to use the if-converted method for all convertible instruments. The update also requires entities to provide expanded disclosures about the terms and features of convertible instruments, how the instruments have been reported in the entity’s financial statements, and information about events, conditions, and circumstances that can affect how to assess the amount or timing of an entity’s future cash flows related to those instruments. The guidance is effective for interim and annual periods beginning after December 15, 2021. The Company adopted this guidance in the first quarter of fiscal 2022 with an immaterial impact to the consolidated financial statements. Recently issued accounting pronouncements - Not yet adopted In March 2020, the FASB issued Accounting Standards Update ASU 2020-04, Reference Rate Reform (Topic 848): Facilitation of the Effects of Reference Rate Reform on Financial Reporting, which provides optional guidance for a limited time to ease the potential burden in accounting for reference rate reform. The new guidance provides optional expedients and exceptions for applying GAAP to contracts, hedging relationships and other transactions affected by reference rate reform if certain criteria are met. The amendments apply only to contracts and hedging relationships that reference the London Interbank Offered Rate (“LIBOR”) or another reference rate expected to be discontinued due to reference rate reform. These amendments are effective immediately and may be applied prospectively to contract modifications made and hedging relationships entered into or evaluated on or before December 31, 2022. We will adopt Topic 848 when our relevant contracts are modified upon transition to alternative reference rates. We do not expect our adoption of Topic 848 to have a material impact on our consolidated financial statements. In October 2021, the FASB issued ASU 2021-08, Business Combinations (Topic 805): Accounting for Contract Assets and Contract Liabilities from Contracts with Customers , which creates an exception to the general recognition and measurement principle for contract assets and contract liabilities from contracts with customers acquired in a business combination. The new guidance will require companies to apply the definition of a performance obligation under ASC Topic 606 to recognize and measure contract assets and contract liabilities (i.e., deferred revenue) relating to contracts with customers that are acquired in a business combination. Under current GAAP, an acquirer in a business combination is generally required to recognize and measure the assets it acquires and the liabilities it assumes at fair value on the acquisition date. The new guidance will result in the acquirer recording acquired contract assets and liabilities on the same basis that would have been recorded by the acquiree before the acquisition under ASC Topic 606. These amendments are effective for fiscal years beginning after December 15, 2022, with early adoption permitted. The Company is evaluating the impact of this standard on our consolidated financial statements. 3. Acquisitions The Company performs quantitative and qualitative analyses to determine the significance of each acquisition to its consolidated financial statements. As such, the acquisitions below were deemed to be insignificant on an individual and cumulative basis. 2022 Acquisitions Acquisitions completed during the year ended December 31, 2022 include the following: 73 • BA Insight - On February 22, 2022, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of BA Insight Inc., (“BA Insight”), a cloud-based enterprise knowledge management solution. Revenues recorded since the acquisition date through December 31, 2022 were approximately $ 7.6 million. • Objectif Lune - On January 07, 2022, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of Objectif Lune Inc., a Quebec proprietary company (“Objectif Lune”), cloud-based document workflow product. Revenues recorded since the acquisition date through December 31, 2022 were approximately $ 20.9 million. We determined that disclosing the amount of BA Insight and Objectif Lune related earnings included in the consolidated statements of operations is impracticable, as certain operations of BA Insight and Objectif Lune were integrated into the operations of the Company from the date of acquisition. 2021 Acquisitions The acquisition completed during the year ended December 31, 2021 include the following: • Panviva - On June 24, 2021, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of Panviva Pty Ltd, an Australian proprietary company (“Panviva”), a cloud-based enterprise knowledge management solution. • BlueVenn - On February 28, 2021 the Company entered into an agreement to purchase the shares comprising the entire issued share capital of BlueVenn Group Limited, a company limited by shares organized and existing under the laws of England and Wales (“BlueVenn”), a cloud-based customer data platform. • Second Street - On January 19, 2021, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of Second Street Media, Inc., a Missouri corporation (“Second Street”), an audience engagement platform. 2020 Acquisitions The acquisition completed during the year ended December 31, 2020 include the following: • Localytics - On February 6, 2020, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of Char Software, Inc (dba Localytics), a Delaware corporation (“Localytics”), a provider of mobile app personalization and analytics solution. Consideration The following table summarizes the consideration transferred for the acquisitions described above (in thousands): BA Insight Objectif Lune Panviva BlueVenn Second Street Localytics Cash $ 33,355 $ 29,750 $ 19,931 $ 53,535 $ 25,436 $ 67,655 Holdback (1) 645 5,250 3,517 2,429 5,000 345 Contingent consideration (2) — — — 2,535 1,650 1,000 Working capital and other adjustments (3) 1,587 644 379 ( 537 ) ( 1,365 ) ( 5,238 ) Total consideration $ 35,587 $ 35,644 $ 23,827 $ 57,962 $ 30,721 $ 63,762 (1) Represents cash holdbacks subject to indemnification claims that are payable 12 months from closing for Objectif Lune, Panviva, Second Street and Localytics, 15 months following closing for BA Insight and 18 months following the closing of BlueVenn. (2) Represents the acquisition date fair value of anticipated earnout payments which are based on the estimated probability of attainment of the underlying future performance-based conditions at the time of acquisition. The maximum potential payout for the BlueVenn, Second Street and Localytics were $ 21.7 million, $ 3.0 million and $ 1.0 million, respectively. As of March 31, 2022, the earnout payments for BlueVenn and Second Street were finalized resulting in no payments made. The earnout for Localytics was paid in full during the year ended December 31, 2020 based on an ending fair value of $ 1.0 million. Refer to “ Note 4. Fair Value Measurements ” for further discussion regarding the calculation of fair value of acquisition related earnouts and subsequent payouts. 74 (3) Working capital and other adjustments includes a $ 5.2 million reduction in total consideration for Localytics related to a representation and warranty insurance settlement which is included in Prepaids and other on our consolidated balance sheets as of December 31, 2020 and a $ 1.4 million reduction in total consideration for Second Street related to an indemnification claim which was charged to Liabilities due to sellers of businesses (Holdback) on our consolidated balance sheets during 2021. Fair Value of Assets Acquired and Liabilities Assumed The Company recorded the purchase of the acquisitions described above using the acquisition method of accounting, and has recognized the assets acquired and liabilities assumed at their fair values as of the date of the acquisition. The purchase accounting for the 2022 acquisition of Objectif Lune is preliminary as the Company has not finalized the overall impact of this acquisition. Management has recorded the purchase price allocations based upon acquired company information that is currently available. Management expects to complete the purchase accounting for Objectif Lune no later than the first quarter of 2023. The following condensed table presents the finalized acquisition-date fair value of the assets acquired and liabilities assumed for the acquisitions closed in 2021 and 2022 (in thousands): Final Preliminary Final BA Insight Objectif Lune Panviva BlueVenn Second Street Year Acquired 2022 2022 2021 2021 2021 Cash $ 4 $ 745 $ 132 $ 1,115 $ — Accounts receivable 2,466 5,677 2,122 1,289 1,105 Other current assets 4,080 7,183 4,985 2,002 89 Operating lease right-of-use asset 110 1,905 197 1,357 489 Property and equipment 3 248 26 611 156 Customer relationships 10,500 17,717 9,757 18,888 14,600 Trade name 150 362 76 238 200 Technology 2,000 5,512 2,194 4,337 3,400 Favorable leases — 291 — — — Goodwill 25,495 23,382 16,604 44,892 16,586 Other assets 25 744 33 24 13 Total assets acquired 44,833 63,766 36,126 74,753 36,638 Accounts payable ( 236 ) ( 2,001 ) ( 1,257 ) ( 2,772 ) ( 230 ) Accrued expense and other ( 4,083 ) ( 9,431 ) ( 5,053 ) ( 2,429 ) ( 378 ) Deferred tax liabilities — ( 5,938 ) ( 2,395 ) ( 3,640 ) ( 4,320 ) Deferred revenue ( 4,817 ) ( 8,847 ) ( 3,397 ) ( 6,593 ) ( 500 ) Operating lease liabilities ( 110 ) ( 1,905 ) ( 197 ) ( 1,357 ) ( 489 ) Total liabilities assumed ( 9,246 ) ( 28,122 ) ( 12,299 ) ( 16,791 ) ( 5,917 ) Total consideration $ 35,587 $ 35,644 $ 23,827 $ 57,962 $ 30,721 The Company uses third party valuation consultants to determine the fair values of assets acquired and liabilities assumed. Tangible assets are valued at their respective carrying amounts, which approximates their estimated fair value. The valuation of identifiable intangible assets reflects management’s estimates based on, among other factors, use of established valuation methods. Customer relationships are valued using the multi-period excess earnings method. Developed technology and trade names are valued using the relief-from-royalty method. 75 The following table summarizes the weighted-average useful lives, by major finite-lived intangible asset class, for intangibles acquired during the years ended December 31, 2022 and 2021 (in years): Useful Life December 31, 2022 December 31, 2021 Customer relationships 7.0 7.0 Trade name 2.0 2.0 Developed technology 6.2 5.0 Favorable Leases 6.3 0.0 Total weighted-average useful life 6.8 6.6 During the measurement period, which may be up to one year from the acquisition date, the Company records adjustments to the assets acquired and liabilities assumed with the corresponding offset to goodwill based on changes to management’s estimates and assumptions. The change in the preliminary acquisition-date fair value of assets and liabilities for BlueVenn and Panviva during the year ended December 31, 2021 was related primarily to an increase in identified intangible assets. The change in the preliminary acquisition-date fair value of assets and liabilities during the year ended December 31, 2022 for Objectif Lune was related primarily to an increase in identified intangible assets. We expect to finalize our analysis of certain tax-related considerations during the first quarter of 2023. The goodwill of $ 127.0 million for the above acquisitions is primarily attributable to the synergies expected to arise after the acquisition. Goodwill deductible for tax purposes related to the above acquisitions was $ 6.6 million. Total transaction costs incurred with respect to acquisition activity in the years ended December 31, 2022, 2021 and 2020 were $ 4.6 million , $ 6.6 million and $ 4.3 million, respectively. These costs are included in Acquisition-related expenses on our consolidated statement of operations. Other Acquisitions and Divestitures From time to time we may purchase or sell customer relationships that meet certain criteria. We had no purchase or sale of customer relationships during the years ended December 31, 2022 and 2021. 4. Fair Value Measurements Fair value is defined as the exit price, or the amount that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants as of the measurement date. GAAP sets forth a three–tier fair value hierarchy, which prioritizes the inputs used in measuring fair value. The three tiers are Level 1, defined as observable inputs, such as quoted market prices in active markets; Level 2, defined as inputs other than quoted prices in active markets that are either directly or indirectly observable; and Level 3, defined as unobservable inputs in which little or no market data exists, which therefore requires an entity to develop its own assumptions. As of December 31, 2022, the Company had no contingent accrued earnout business acquisition consideration liabilities for which fair values are measured as Level 3 instruments. As of December 31, 2021, the Company had contingent accrued earnout business acquisition consideration liabilities for which fair values are measured as Level 3 instruments. These contingent consideration liabilities were recorded at fair value on the acquisition date and are remeasured periodically based on the then assessed fair value and adjusted, if necessary. The increases or decreases in the fair value of contingent consideration payable can result from changes in anticipated revenue levels or changes in assumed discount periods and rates. As the fair value measure is based on significant inputs that are not observable in the market, they are categorized as Level 3. Any gain (loss) related to subsequent changes in the fair value of contingent consideration is recorded in Acquisition-related expense or Other income (expense), net on our consolidated statements of operations based on management's assessment of the nature of the liability. Earnout consideration liabilities are included in Liabilities due to sellers of businesses on our consolidated balance sheets. In connection with entering into, and expanding, the Company's credit facility, as discussed further in “ Note 7. Debt ”, the Company entered into interest rate swaps for the full 7 year term of the Company’s term loans, effectively fixing our interest rate at 5.4 % for the full value of the Company’s term loans. The fair value of this swap is measured at the end of each interim reporting period based on the then assessed fair value and adjusted if necessary. As the fair value measure is based on the market approach, they are categorized as Level 2. As of December 31, 2022, the fair value of the interest rate swaps is included in the “ Interest rate swap assets ” section compared to December 31, 2021 in which the fair value of the interest rate swaps included in the liabilities section on the Company's consolidated balance sheets. 76 On February 21, 2023, the Company entered into an amendment to its Credit Facility. The amendment amended the interest rate benchmark from LIBOR to Secured Overnight Financing Rate (“SOFR”). See “ Note 18. Subsequent Events ” for further details. Liabilities measured at fair value on a recurring basis are summarized below (in thousands): Fair Value Measurements at December 31, 2022 Level 1 Level 2 Level 3 Total Assets: Cash equivalents - money market funds $ 172,849 $ — $ — $ 172,849 Interest rate swap asset $ — $ 41,168 $ — $ 41,168 $ 172,849 $ 41,168 $ — $ 214,017 Fair Value Measurements at December 31, 2021 Level 1 Level 2 Level 3 Total Liabilities: Interest rate swap liability $ — $ 8,409 $ — $ 8,409 The following table presents additional information about earnout consideration liabilities measured at fair value on a recurring basis and for which we have utilized significant unobservable (Level 3) inputs to determine fair value: December 31, 2022 2021 Beginning balance $ — $ — Remeasurement adjustments: (Gain) loss included in earnings — ( 4,169 ) Foreign currency translation adjustments — ( 16 ) Acquisitions and settlements: Acquisitions — 4,185 Settlements — — Ending balance $ — $ — Sensitivity to Changes in Significant Unobservable Inputs As presented in the table above, the significant unobservable inputs used in the fair value measurement of contingent consideration related to business acquisitions are forecasts of expected future annual revenues as developed by the Company's management and the probability of achievement of those revenue forecast. Significant increases (decreases) in these unobservable inputs in isolation would likely result in a significantly (lower) higher fair value measurement. Debt The Company believes the carrying value of its long-term debt at December 31, 2022 approximates its fair value based on the variable interest rate feature or based upon interest rates currently available to the Company. The estimated fair value and carrying value of the Company's debt, before debt discount, at December 31, 2022 and December 31, 2021 are $ 522.5 million and $ 527.9 million, respectively, based on valuation methodologies using interest rates currently available to the Company which are Level 2 inputs. 77 5. Goodwill and Other Intangible Assets Changes in the Company’s Goodwill balance for each of the two years in the period ended December 31, 2022 are summarized in the table below (in thousands): Goodwill Adjustments Balance at December 31, 2020 $ 383,598 Acquired in business combinations 85,102 Adjustment related to finalization of business combinations ( 7,266 ) Foreign currency translation adjustment ( 3,962 ) Balance at December 31, 2021 $ 457,472 Acquired in business combinations 48,768 Adjustment related to prior year business combinations 1,466 Adjustment related to finalization of current year business combinations 109 Impairment of goodwill (1) ( 12,500 ) Foreign currency translation adjustment and other ( 18,272 ) Balance at December 31, 2022 $ 477,043 (1) Refer to discussion herein and in Note 2. Basis of Presentation and Summary of Significant Accounting Policies—Goodwill and Other Intangible s. We performed the annual goodwill impairment test and did not identify an impairment. As a result of the decline of our stock price impacting our market capitalization during the quarter ended December 31, 2022, we performed a quantitative impairment evaluation as of December 31, 2022, which resulted in a Goodwill impairment of $12.5 million. This quantitative goodwill impairment analysis applied two methodologies to estimate the Company’s fair value which were: a) a discounted cash flow method and b) a guideline public company method. The two methods generated similar results and indicated that the fair value of the Company was less than its carrying value. The discounted cash flow method requires significant judgments, including estimation of future cash flows, which is dependent on internally developed forecasts, estimation of the long-term rate of growth for our business, and determination of our weighted average cost of capital. Under the guideline public company method, we estimate fair value based on a market multiple of revenues and earnings derived for comparable publicly traded companies with similar operating characteristics as the Company. We did not record a goodwill impairment charge for the years ended December 31, 2021 or 2020. Intangible assets, net, include the estimated acquisition-date fair values of customer relationships, marketing-related assets and developed technology that the Company recorded as part of its business acquisitions purchases and from acquisitions of customer relationships. The following is a summary of the Company’s Intangible assets, net (in thousands): Estimated Useful Life (Years) Gross Carrying Amount Accumulated Amortization Net Carrying Amount December 31, 2022 Customer relationships 1 - 10 $ 372,162 $ 162,995 $ 209,167 Trade name 1.5 - 10 9,837 6,728 3,109 Developed technology 4 - 9 92,585 56,240 36,345 Favorable leases 6.3 $ 273 $ 43 $ 230 Total intangible assets $ 474,857 $ 226,006 $ 248,851 Estimated Useful Life (Years) Gross Carrying Amount Accumulated Amortization Net Carrying Amount December 31, 2021 Customer relationships 1 - 10 $ 358,943 $ 126,329 $ 232,614 Trade name 1.5 - 10 9,714 5,752 3,962 Developed technology 4 - 9 88,548 45,204 43,344 Non-compete agreements 3 1,148 1,148 — Total intangible assets $ 458,353 $ 178,433 $ 279,920 78 The Company periodically reviews the estimated useful lives of its identifiable intangible assets, taking into consideration any events or circumstances that might result in either a diminished fair value or revised useful life. Total amortization expense was $ 54.6 million, $ 50.9 million, and $ 44.9 million for the years ended December 31, 2022, 2021 and 2020, respectively. There were no material changes in the useful life of our intangible assets during the years ended December 31, 2022, 2021 and 2020. During the fourth quarter of 2022, the Company reduced the estimated useful life for certain product offerings, which will result in higher estimated amortization expense in 2023. No impairment of intangible assets were recorded during the years ended December 31, 2022, 2021 and 2020. As of December 31, 2022, the estimated annual amortization expense for the next five years and thereafter is as follows (in thousands): Year ending December 31: Amortization Expense 2023 71,825 2024 55,798 2025 34,823 2026 32,606 2027 28,373 Thereafter $ 25,426 Total $ 248,851 79 6. Income Taxes The Company's loss from continuing operations before income taxes for the year ended December 31, was as follows (in thousands): Year Ended December 31, 2022 2021 2020 Loss before provision for income taxes: United States $ ( 40,818 ) $ ( 53,981 ) $ ( 43,851 ) Foreign ( 29,336 ) ( 12,575 ) ( 11,602 ) $ ( 70,154 ) $ ( 66,556 ) $ ( 55,453 ) The components of the provision (benefit) for income taxes attributable to continuing operations are as follows (in thousands): Year Ended December 31, 2022 2021 2020 Current Federal $ — $ — $ — State 971 363 402 Foreign 4,776 2,349 2,449 Total Current $ 5,747 $ 2,712 $ 2,851 Deferred Federal $ 84 $ ( 5,180 ) $ ( 2,275 ) State 1,062 ( 1,033 ) ( 137 ) Foreign ( 8,634 ) ( 4,843 ) ( 4,673 ) Total Deferred ( 7,488 ) ( 11,056 ) ( 7,085 ) (Benefit from) provision for income taxes $ ( 1,741 ) $ ( 8,344 ) $ ( 4,234 ) As of December 31, 2022 the Company had total net operating loss carryforwards of approximately $ 357.8 million consisting of $ 301.6 million and $ 56.1 million related to the U.S federal and foreign net operating loss carryforwards, respectively. In addition, as of December 31, 2022, the Company had research and development credit carryforwards of approximately $ 4.1 million. The U.S. federal net operating loss and credit carryforwards will expire beginning in 2023, if not utilized. Utilization of the U.S. federal net operating losses and tax credits may be subject to substantial annual limitation due to the “change of ownership” provisions of the Internal Revenue Code of 1986. The annual limitation will result in the expiration of approximately $ 155.0 million of U.S. federal net operating losses and $ 4.1 million of credit carryforwards before utilization.$ 50.3 million of foreign net operating loss carryforwards carry forward indefinitely, and the remainder will expire beginning in 2041. 80 Deferred income taxes reflect the net tax effects of temporary differences between the carrying amounts of assets and liabilities for financial reporting purposes and the amounts used for income tax purposes. Significant components of the Company’s deferred taxes as of December 31 are as follows (in thousands): As of December 31, 2022 2021 2020 Deferred tax assets: Accrued expenses and allowances $ 1,640 $ 2,197 $ 2,095 Deferred revenue 608 536 613 Stock compensation 612 1,558 1,151 Net operating loss and tax credit carryforwards 52,149 53,388 53,157 Disallowed interest expense carryforwards 17,181 15,654 11,599 Capital expenses 295 321 286 Tax credit carryforwards 348 — 600 Lease liability 2,139 2,340 3,054 Unrealized losses — 1,974 7,617 Research and development expenses 6,243 — — Other 461 638 658 Valuation allowance ( 20,482 ) ( 28,627 ) ( 35,701 ) Net deferred tax assets $ 61,194 $ 49,979 $ 45,129 Deferred tax liabilities: Prepaid expenses $ ( 161 ) $ ( 272 ) $ ( 260 ) Intangible assets ( 54,153 ) ( 59,092 ) ( 56,541 ) Goodwill ( 7,382 ) ( 6,570 ) ( 5,954 ) Tax credit carryforwards — ( 99 ) — Right of use asset ( 1,504 ) ( 1,330 ) ( 2,597 ) Unrealized gains ( 10,705 ) — — Deferred commissions ( 5,705 ) ( 5,409 ) ( 3,869 ) Net deferred tax liabilities $ ( 79,610 ) $ ( 72,772 ) $ ( 69,221 ) Net deferred taxes $ ( 18,416 ) $ ( 22,793 ) $ ( 24,092 ) Due to the uncertainty surrounding the timing of realizing the benefits of its domestic favorable tax attributes in future tax returns, the Company has placed a valuation allowance against its domestic net deferred tax assets, exclusive of goodwill. During the years ended December 31, 2022 and 2021, the valuation allowance decreased by approximately $ 8.1 million and $ 7.1 million, respectively. The valuation allowance for the year ended December 31, 2022 decreased by approximately $ 13.0 million due to the tax effect of items recorded in other comprehensive income with the remaining increase of approximately $ 4.9 million related primarily to current operations. The valuation allowance for the year ended December 31, 2021 decreased by approximately $ 5.7 million due to the tax effect of items recorded in other comprehensive income and approximately $ 6.4 million due to acquired net deferred tax liabilities as a result of domestic business combinations, which was recorded as an income tax benefit, which is partially offset with the remaining increase of approximately $ 5.0 million related primarily to current operations. At December 31, 2022, we did not provide deferred income taxes on temporary differences resulting from earnings of certain foreign subsidiaries which are indefinitely reinvested. The reversal of these temporary differences could result in additional tax; however, it is not practicable to estimate the amount of any unrecognized deferred income tax liabilities at this time. Deferred income taxes are provided as necessary with respect to earnings that are not indefinitely reinvested. 81 The Company’s provision for income taxes differs from the expected tax expense (benefit) computed by applying the statutory federal income tax rate to income before taxes due to the following: Year Ended December 31, 2022 2021 2020 Federal statutory rate 21.0 % 21.0 % 21.0 % State taxes, net of federal benefit ( 0.2 ) % 1.5 % 1.6 % Tax credits 0.6 % 0.6 % ( 0.1 ) % Effect of foreign operations 0.1 % ( 0.6 ) % ( 1.1 ) % Stock compensation ( 9.5 ) % ( 5.4 ) % ( 0.3 ) % Disallowed excess executive compensation ( 0.6 ) % ( 5.3 ) % ( 4.0 ) % Goodwill impairment ( 3.6 ) % — % — % Permanent items and other ( 0.5 ) % 0.1 % ( 0.7 ) % Change in valuation allowance ( 6.9 ) % 1.1 % ( 8.8 ) % Change in tax rates 2.1 % ( 2.6 ) % — % Australia tax basis uplift — % 2.1 % — % 2.5 % 12.5 % 7.6 % Under ASC 740-10, Income Taxes - Overall , the Company periodically reviews the uncertainties and judgments related to the application of complex income tax regulations to determine income tax liabilities in several jurisdictions. The Company uses a “more likely than not” criterion for recognizing an asset for unrecognized income tax benefits or a liability for uncertain tax positions. The Company has determined it has the following unrecognized assets or liabilities related to uncertain tax positions as of December 31, 2022. It is reasonably possible that a reduction of $0.8 million of unrecognized tax benefits may occur within the next 12 months due to the expiration of statutes of limitation, affecting our net income tax provision and therefore benefit the resulting tax rate. The actual amount could vary depending on any actual settlement prior to the expiration of statutes of limitation. To the extent the Company is required to recognize interest and penalties related to unrecognized tax liabilities, this amount will be recorded as an accrued liability, (in thousands). Balance at December 31, 2020 $ 610 Additional based on tax positions related to the current year — Additions for tax positions of prior years 162 Reductions for tax positions of prior years — Settlements — Balance at December 31, 2021 $ 772 Additional based on tax positions related to the current year — Additions for tax positions of prior years 45 Reductions for tax positions of prior years — Settlements — Balance at December 31, 2022 $ 817 If the Company were to recognize unrecognized tax benefits as of December 31, 2022, $ 0.8 million would impact the effective tax rate. The Company’s assessment of its unrecognized tax benefits is subject to change as a function of the Company’s financial statement audit. The Company recognizes interest and penalties related to uncertain tax positions in income tax expense. As of December 31, 2022, the Company had accrued $ 0.4 million of interest or penalties related to uncertain tax positions, which is reasonably possible to reverse in the next 12 months. The Company and its subsidiaries file tax returns in the U.S. federal jurisdiction and in several state and foreign jurisdictions. The Company is no longer subject to U.S. federal income tax examinations for years ending before December 31, 2018 and is no longer subject to state and local or foreign income tax examinations by tax authorities for years ending before December 31, 2017. The Company is not currently under audit for federal, state or any foreign jurisdictions. US operating losses generated in years prior to 2018 remain open to adjustment until the statute of limitations closes for the tax year in which the net operating losses are utilized. 82 7. Debt Long-term debt consisted of the following at December 31, 2022 and December 31, 2021 (in thousands): December 31, 2022 2021 Senior secured loans (includes unamortized discount of $ 7,467 and $ 9,520 based on an imputed interest rate of 5.8 % and 5.8 %, at December 31, 2022 and December 31, 2021, respectively) $ 514,983 $ 518,330 Less current maturities ( 3,136 ) ( 3,167 ) Total long-term debt $ 511,847 $ 515,163 Credit Facility On August 6, 2019, the Company entered into a credit agreement (the “Credit Facility”) which provides for (i) a fully-drawn $ 350 million, 7 year, senior secured term loan B facility (the “Term Loan”) and (ii) a $ 60 million, 5 year, revolving credit facility (the “Revolver”) that was fully available as of December 31, 2022. The Credit Facility replaced the Company's previous credit facility. All outstanding balances under our previous credit facility were paid off using proceeds from our Credit Facility. On November 26, 2019 (the “Closing Date”), the Company entered into a First Incremental Assumption Agreement (the “Incremental Assumption Agreement”) which provides for a term loan facility to be established under the Credit Facility in an aggregate principal amount of $ 190.0 million (the “2019 Incremental Term Loan”), which is in addition to the existing $ 350 million term loans outstanding under the Credit Facility and the $ 60 million Revolver under the Credit Facility. Payment terms The Term Loans (including the 2019 Incremental Term Loan) are repayable on a quarterly basis beginning on December 31, 2019 by an amount equal to 0.25 % ( 1.00 % per annum) of the aggregate principal amount of such loan. Any amount remaining unpaid is due and payable in full on August 6, 2026 (the “Term Loan Maturity Date”). At the option of the Company, the Term Loans (including the 2019 Incremental Term Loan) accrue interest at a per annum rate based on (i) the Base Rate plus a margin of 2.75 % or (ii) the rate (not less than 0.00 %) for Eurodollar deposits quoted on the LIBOR01 or LIBOR02 pages on the Reuters Screen, or as otherwise determined in accordance with the Credit Facility (based on a period equal to 1, 2, 3 or 6 months or, if available and agreed to by all relevant Lenders and the Agent, 12 months or such period of less than 1 month) plus a margin of 3.75 %. The Base Rate for any day is a rate per annum equal to the greatest of (i) the prime rate in effect on such day, (ii) the federal funds effective rate (not less than 0.00 %) in effect on such day plus ½ of 1.00%, and (ii) the Eurodollar rate for a one month interest period beginning on such day plus 1.00 %. On February 21, 2023, the Company entered into an amendment to its Credit Facility. The amendment amended the interest rate benchmark from LIBOR to SOFR. Other than the foregoing, the material terms of the Credit Agreement remains unchanged. See “ Note 18. Subsequent Events ” for further details. Accrued interest on the loans will be paid quarterly or, with respect to loans that are accruing interest based on the Eurodollar rate, at the end of the applicable interest rate period. Interest rate swaps On August 6, 2019, the Company entered into an interest rate hedge instrument for the full 7 year term, effectively fixing our interest rate at 5.4 % for the Term Loan. In addition, on November 26, 2019, the Company entered into interest rate swap agreements to hedge the interest rate risk associated with the Company’s floating rate obligations under the 2019 Incremental Term Loan. These interest rate swaps fix the Company's interest rate (including the hedge premium) at 5.4 % for the term of the Credit Facility. The interest rate associated with our new $ 60 million, 5 year, Revolver remains floating. The interest rate swap has been designated as a cash flow hedge and is valued using a market approach, which is a Level 2 valuation technique. At December 31, 2022, the fair value of the interest rate swap was a $ 41.2 million asset as a result of an increase in short term interest rates from 2021 to 2022. In the next twelve months, the Company estimates that $ 11.6 million will be reclassified from Accumulated other comprehensive income (loss) to Interest expense, net on our consolidated statement of operations. 83 Year Ended December 31 2022 2021 2020 Unrealized gain (loss) recognized in Other comprehensive income (loss) on interest rate swaps $ 49,577 $ 21,623 $ ( 32,455 ) Gain (loss) on interest rate swap (included in Interest expense, net on our consolidated statement of operations) $ 283 $ ( 8,250 ) $ ( 5,500 ) Revolver Loans under the Revolver are available up to $ 60 million, of which none is currently outstanding. The Revolver provides a sub facility whereby the Company may request letters of credit (the “Letters of Credit”) in an aggregate amount not to exceed, at any one time outstanding, $ 10.0 million for the Company. The aggregate amount of outstanding Letters of Credit are reserved against the credit availability under the Maximum Revolver Amount. The Company incurs a 0.50 % per annum unused line fee on the unborrowed balance of the Revolver which is paid quarterly. Loans under the Revolver may be borrowed, repaid and reborrowed until August 6, 2024 (the “Maturity Date”), at which time all amounts borrowed under the Revolver must be repaid. As of December 31, 2022, the Company had no borrowings outstanding under the Revolver or related sub facility. Covenants The Credit Facility contains customary affirmative and negative covenants. The negative covenants limit the ability of the Loan Parties to, among other things (in each case subject to customary exceptions for a credit facility of this size and type): • Incur additional indebtedness or guarantee indebtedness of others; • Create liens on our assets; • Make investments, including certain acquisitions; • Enter into mergers or consolidations; • Dispose of assets; • Pay dividends and make other distributions on the Company’s capital stock, and redeem and repurchase the Company’s capital stock; • Enter into transactions with affiliates; and • Prepay indebtedness or make changes to certain agreements. The Credit Facility has no financial covenants as long as less than 35 % of the Revolver is drawn as of the last day of any fiscal quarter. If 35 % of the Revolver is drawn as of the last day of a given fiscal quarter, the Company will be required to maintain a Total Leverage Ratio (the ratio of funded indebtedness as of such date less the amount of unrestricted cash and cash equivalents of the Company and its guarantors in an amount not to exceed $ 50.0 million, to Adjusted EBITDA (calculated on a pro forma basis including giving effect to any acquisition)), measured on a quarter-end basis for each four consecutive fiscal quarters then ended, of not greater than 6.00 to 1.00. The Credit Facility contains customary events of default subject to customary cure periods for certain defaults that include, among others, non-payment defaults, inaccuracy of representations and warranties, covenant defaults, cross-defaults to certain other material indebtedness, change in control, bankruptcy and insolvency defaults and material judgment defaults. The occurrence of an event of default could result in the acceleration of Term Loans and Revolver and a right by the agent and lenders to exercise remedies. At the election of the lenders, a default interest rate shall apply on all obligations during an event of default, at a rate per annum equal to 2.00 % above the applicable interest rate. The Term Loan and Revolver are secured by substantially all of the Company's assets. As of December 31, 2022 the Company was in compliance with all covenants under the Credit Facility. Cash interest costs averaged 5.4 % for both the years ended December 31, 2022 and 2021, respectively. As of December 31, 2022, the Company had $ 7.5 million of unamortized debt issuance costs associated with the Credit Facility. These issuance costs will be amortized to Interest expense, net on our consolidated statement of operations, over the term of the Credit Facility. 84 Debt Maturities Under the terms of the Credit Facility, future debt maturities of long-term debt excluding debt discounts at December 31, 2022 are as follows (in thousands): Year ending December 31: Amount 2023 $ 5,400 2024 5,400 2025 5,400 2026 506,250 Total debt outstanding $ 522,450 Less unamortized discount 7,467 Total debt outstanding, net of discount $ 514,983 85 8. Net Loss Per Share We compute loss per share of our Common Stock and Series A Preferred Stock using the two-class method. The two-class method requires income available to common stockholders for the period to be allocated between common stock and participating securities based upon their respective rights to receive dividends as if all income for the period had been distributed. We consider our Series A Preferred Stock to be a participating security, as its holders are entitled to fully participate in any dividends or other distributions declared or paid on our Common Stock on an as-converted basis. The following table sets for the computations of loss per share: Year Ended December 31, (In thousands, except share and per share amounts) 2022 2021 2020 Numerators: Net loss $ ( 68,413 ) $ ( 58,212 ) $ ( 51,219 ) Preferred stock dividends and accretion ( 1,846 ) — — Net loss attributable to common stockholders $ ( 70,259 ) $ ( 58,212 ) $ ( 51,219 ) Denominator: Weighted–average common shares outstanding, basic and diluted 31,528,881 30,295,769 26,632,116 Net loss per common share, basic and diluted $ ( 2.23 ) $ ( 1.92 ) $ ( 1.92 ) Due to the net losses incurred for the years ended December 31, 2022, 2021 and 2020, basic and diluted loss per share were the same, as the effect of all potentially dilutive securities would have been anti-dilutive. The Company adopted ASU 2020-06 on January 1, 2022 as detailed in “ Note 2. Basis of Presentation and Summary of Significant Accounting Policies—Recent Accounting Pronouncements—Recently issued accounting pronouncements - Adopted .” As such, the Company is required to use the application of the if-converted method for calculating diluted earnings per share on our Series A Preferred Stock. The Company applies the treasury stock method for calculating diluted earnings per share on our stock options, restricted stock awards, restricted stock units and performance restricted stock units. The following table sets forth the anti-dilutive common share equivalents excluded from the weighted-average shares used to calculate diluted net loss per common share: Year Ended December 31, 2022 2021 2020 Stock options 154,321 227,605 264,002 Restricted stock awards (1) — — 34,508 Restricted stock units 1,509,273 1,379,747 1,261,290 Performance restricted stock units 93,750 63,537 66,297 Series A Preferred Stock on an as-converted basis (2) 6,676,923 — — Total anti–dilutive common share equivalents 8,434,267 1,670,889 1,626,097 (1) All outstanding restricted stock awards became fully vested as of December 31, 2021. (2) Per ASU 2020-06, the Company is applying the if-converted method to calculated diluted earnings per share. As of December 31, 2022, the Series A Preferred Stock plus accumulated dividends totaled $ 116.8 million. The Series A Preferred Stock has a conversion price of $ 17.50 per share, as detailed in “ Note 12. Series A Preferred Stock” 9. Leases Operating Leases The Company leases office space under operating leases that expire between 2023 and 2028. The terms of the Company's non-cancelable operating lease arrangements typically contain fixed rent increases over the term of the lease, rent holidays and provide for additional renewal periods. Rent expense on these operating leases is recognized over the term of the lease on a straight-line basis. 86 Finance Leases The current and long-term portion of finance lease obligations are included in Accrued expenses and other current liabilities and Other long-term liabilities line items on the consolidated balance sheet, respectively. The Company had no finance lease agreements since December 31, 2021. Lease Expense Total office rent expense for the years ended December 31, 2022, 2021 and 2020 were approximately $ 2.5 million, $ 6.2 million and $ 5.9 million , respectively. The $ 2.5 million office rent expense in 2022 includes approximately $ 1.1 million of transformation charges in conjunction with the closures of the BA Insight and Objectif Lune offices as we continue to consolidate and integrate these acquisitions. The $ 6.2 million office rent expense in 2021 includes approximately $ 4.4 million of transformation charges in conjunction with the closures of the the Panviva, BlueVenn, Second Street and Localytics offices as we continue to consolidate and integrate these acquisitions. The Company has entered into sublease agreements related to excess office space as a result of the Company's transformation activities related to its acquisitions. The Company’s current sublease agreements terminate in 2027. For the years ended December 31, 2022, 2021 and 2020, the Company recognized rental income on subleases, as offsets to rental expense, of $ 1.4 million, $ 1.1 million and $ 0.8 million, respectively. Operating lease obligations in the future minimum payments table below do not include the impact of future rental income of $ 2.5 million related to these subleases as of December 31, 2022. The components of lease expense were as follows (in thousands): Year Ended December 31, 2022 2021 Operating lease cost $ 3,959 7,279 Finance lease costs: Amortization of right-of-use assets — 29 Interest on lease liabilities — — Sublease income ( 1,428 ) ( 1,068 ) Total lease expense $ 2,531 6,240 Other information about lease amounts recognized on our consolidated financial statements is summarized as follows: Year Ended December 31, 2022 2021 Cash paid for amounts included in the measurement of lease liabilities (in thousands): Operating cash flows from operating leases $ 4,658 $ 4,111 Financing cash flows from finance leases $ — $ 12 Right-of-use assets obtained in exchange for lease obligations (in thousands): Operating leases $ 1,943 $ 2,748 Weighted average remaining lease term (in years): Operating leases 3.2 3.6 Weighted average discount rate Operating leases 5.4 % 5.4 % 87 As of December 31, 2022, the Company no longer had any finance lease agreements. Future minimum payments for operating lease obligations and purchase commitments are as follows (in thousands): Operating Leases 2023 $ 3,711 2024 2,554 2025 1,792 2026 1,194 2027 260 Thereafter 72 Total minimum lease payments 9,583 Less amount representing interest ( 1,431 ) Present value of lease liabilities $ 8,152 Operating lease liabilities, current 3,205 Operating lease liabilities, noncurrent 4,947 Total lease liabilities $ 8,152 10. Commitments and Contingencies Purchase Commitments The Company has purchase commitments related to hosting services, third-party technology used in the Company's solutions and for other services the Company purchases as part of normal operations. In certain cases these arrangements require a minimum annual purchase commitment. Future minimum payments for purchase commitments are as follows (in thousands): Year Purchase Commitments 2023 $ 23,158 2024 11,568 2025 6,694 2026 — 2027 — Thereafter — Total minimum payments $ 41,420 Litigation In the normal course of business, the Company may become involved in various lawsuits and legal proceedings. As of December 31, 2022, the Company is not involved in any current or pending legal proceedings, and does not anticipate any legal proceedings, that may have a material adverse effect on its consolidated financial position or results of operations. In addition, when we acquire companies, we require that the sellers provide industry standard indemnification for breaches of representations and warranties contained in the acquisition agreement and we will withhold payment of a portion of the purchase price for a period of time in order to satisfy any claims that we may make for indemnification. In certain transactions, we agree with the sellers to purchase a representation and warranty insurance policy that will pay such claims for indemnification. From time to time we may have one or more claims for indemnification pending. Similarly, we may have one or more ongoing negotiations related to the amount of an earnout. Gain contingencies related to indemnification claims are not recognized on our consolidated financial statements until realized. 88 11. Property and Equipment, Net Property and equipment consisted of the following (in thousands) at: December 31, 2022 2021 Equipment $ 6,211 $ 15,327 Furniture and fixtures 355 668 Leasehold improvements 1,037 1,766 Accumulated depreciation ( 5,773 ) ( 15,094 ) Property and equipment, net $ 1,830 $ 2,667 Amortization of assets recorded under finance leases is included with depreciation expense. Depreciation and amortization expense on Property and equipment, net was $ 1.5 million, $ 2.0 million and $ 2.2 million for the years ended December 31, 2022, 2021 and 2020, respectively. The Company recorded no impairment of property and equipment during the years ended December 31, 2022, 2021 and 2020. During the years ended December 31, 2022, 2021 and 2020, we recognized a $ 0.1 million,$ 0.0 million and $ 0.6 million loss on disposal of assets related primarily to leasehold improvements associated with the consolidation and integration of prior year acquisitions. 12. Series A Preferred Stock On July 14, 2022, the Company entered into a Securities Purchase Agreement (the “Purchase Agreement”) with Ulysses Aggregator, LP (the “Purchaser”), an affiliate of HGGC, LLC, to issue and sell at closing 115,000 shares of Series A Preferred Stock of the Company, par value $ 0.0001 per share, at a price of $ 1,000 per share (the “Initial Liquidation Preference”) for an aggregate purchase price of $ 115.0 million (the “Investment”). The Company will use the proceeds of the Investment (a) for general corporate purposes and (b) for transaction-related fees and expenses. On August 23, 2022 (the “Closing Date”), the closing of the Investment (the “Closing”) occurred, and the Series A Preferred Stock was issued to the Purchaser. In connection with the issuance of the Series A Preferred Stock, the Company incurred direct and incremental expenses comprised of transaction fees, and financial advisory and legal expenses (the “Series A Preferred Stock Issuance Costs”), which reduced the carrying value of the Series A Preferred Stock. As of December 31, 2022, the Series A Preferred Stock Issuance Costs totaled $ 4.6 million. Cumulative preferred dividends accrue quarterly on the Series A Preferred Stock at a rate of 4.5 % per year within the first seven years after the Closing Date regardless of whether declared or assets are legally available for the payment. Such dividends shall accrue and compound quarterly in arrears from the date of issuance of the shares. The dividend rate will increase to 7.0 % on the seven-year anniversary of the Closing Date. The Series A Preferred Stock had accrued unpaid dividends of $ 1.8 million as of December 31, 2022. Contemporaneous with the Closing Date, the Company and the Purchaser entered into a Registration Rights Agreement (the “Registration Rights Agreement”) and the Company filed a Certificate of Designation (the “Certificate of Designation”) setting out the powers, designations, preferences, and other rights of the Series A Preferred Stock with the Secretary of State of the State of Delaware in connection with the Closing. Pursuant to the Registration Rights Agreement, the Purchaser has certain customary registration rights with respect to any shares of Series A Preferred Stock or the common stock of the Company issuable upon conversion of the Series A Preferred Stock, including rights with respect to the filing of a shelf registration statement, underwritten offering rights and piggy back rights. Dividend Provisions 89 The Series A Preferred Stock rank senior to the Company’s common stock with respect to payment of dividends and rights on the distribution of assets on any liquidation, dissolution or winding up of the affairs of the Company. The Series A Preferred Stock has an Initial Liquidation Preference of $ 1,000 per share, representing an aggregate Liquidation Preference (as defined below) of $ 1,000 upon issuance. Holders of the Series A Preferred Stock are entitled to the dividend at the rate of 4.5 % per annum, within first seven years after the Closing Date regardless of whether declared or assets are legally available for the payment. Such dividends shall accrue and compound quarterly in arrears from the date of issuance of the shares. The dividend rate will increase to 7.0 % on the seven-year anniversary of the Closing Date. The dividend can be paid, in the Company’s sole discretion, in cash or dividend in kind by adding to the Liquidation Preference of each share of Series A Preferred Stock outstanding; provided that, until the stockholder approvals contemplated by Nasdaq Global Market Listing Standard Rules 5635(a), (b) and (d) are obtained, as applicable, the Company may not pay in kind if doing so would cause the common shares issuable upon conversion of the Preferred Stock to exceed 19.9 % of the total outstanding common stock as of the Closing Date. The Series A Preferred Stock is also entitled to fully participate in any dividends paid to the holders of common stock in cash, in stock or otherwise, on an as-converted basis. Liquidation Rights In the event of any Liquidation, holders of the Series A Preferred Stock are entitled to receive an amount per share equal to the greater of (1) the Initial Liquidation Preference per share plus any accrued or declared but unpaid dividends on such shares (the “Liquidation Preference”) or (2) the amount payable if the Series A Preferred Stock were converted into common stock. The Series A Preferred Stock will have distribution and liquidation rights senior to all other equity interests of the Company. As of December 31, 2022, the Liquidation Preference of the Series A Preferred Stock was $ 116.8 million. Optional Redemption On or after the 7th anniversary of the original issue date of the Series A Preferred Stock, the Company has the right to redeem any outstanding shares of the Series A Preferred Stock for a cash purchase price equal to 105 % of the Liquidation Preference plus accrued and unpaid dividends as of the date of redemption. Deemed Liquidation Event Redemption Upon a fundamental change, holders of the Series A Preferred Stock have the right to require the Company to repurchase any or all of its Series A Preferred Stock for cash equal to the greater of (1) 105 % of the Liquidation Preference plus the present value of the dividend payments the holders would have been entitled to through the fifth anniversary of the issue date and (2) the amount that such Preferred Stock would have been entitled to receive as if converted into common shares immediately prior to the fundamental change. A fundamental change (“Deemed Liquidation Event”) is defined as either the direct or indirect sale, lease, transfer, conveyance or other disposition of all or substantially all the properties or assets of the Company and its subsidiaries to any third party or the consummation of any transaction, the result of which is that any third party or group of third parties become the beneficial owner of more than 50 % of the voting power of the Company. Voting Rights The Series A Preferred Stock will vote together with the Common Shares on all matters and not as a separate class (except as specifically provided in the Certificate of Designation or as otherwise required by law) on an as-if-converted basis. The holders of the Series A Preferred Stock will have the right to elect one member of the Board of Directors for so long as holders of the Series A Preferred Stock own in the aggregate at least 5 % of the shares of common stock on a fully diluted basis. In addition, the holders of the Series A Preferred Stock will have the right to elect one non-voting observer to the Board of Directors for so long as they hold at least 10 % of the shares of Convertible Preferred Stock outstanding as of the date of the issue date. Conversion Feature 90 The Series A Preferred Stock may be converted, at any time in whole or in part at the option of the holder into a number of shares of common stock equal to the quotient obtained by dividing the sum of the Liquidation Preference plus all accrued and unpaid dividends by the conversion price of $ 17.50 (the “Conversion Price”). The Conversion Price is subject to adjustment in the following events: • Stock splits and combinations • Tender offers or exchange offers • Distribution of rights, options, or warrants at a price per share that is less than the average of the last reported sale prices per share of Common Stock for the ten consecutive trading days • Spin-offs and other distributed property • Issuance of equity-linked securities at a price per share less than the conversion price Anti-Dilution Provisions The Series A Preferred Stock has customary anti-dilution provisions for stock splits, stock dividends, mergers, sales of significant assets, and reorganization events and recapitalization transactions or similar events, and weighted average anti-dilution protection, subject to customary exceptions for issuances pursuant to current or future equity-based incentive plans or arrangements (including upon the exercise of employee stock options). 13. Stockholders' Equity Common and Preferred Stock Our certificate of incorporation authorizes shares of stock as follows: 50,000,000 shares of common stock and 5,000,000 shares of preferred stock. The common and preferred stock has a par value of $ 0.0001 per share. See “ Note 12. Series A Preferred Stock ” for a description of our Series A Preferred Stock, which is the only class of preferred stock outstanding. Each share of common stock is entitled to one vote at all meetings of stockholders. The number of authorized shares of common stock may be increased or decreased (but not below the number of shares thereof then outstanding) by the affirmative vote of the holders of shares of capital stock of the Company representing a majority of the votes represented by all outstanding shares of capital stock of the Company entitled to vote. The holders of common stock are also entitled to receive dividends, when, if and as declared by our board of directors, whenever funds are legally available therefore, subject to the priority rights of any outstanding preferred stock. Registration Statements 2022 S-3 On October 21, 2022 we filed a resale registration statement on Form S-3 (File No. 333-267973) (the “2022 S-3”), on behalf of the Purchaser and pursuant to the Registration Rights Agreement, which became effective on November 1, 2022 and covers (i) the issued Series A Preferred Stock and (ii) the number of shares of the Company’s common stock issuable upon conversion of such Series A Preferred Stock, which amount includes and assumes that dividends on the Series A Preferred Stock are paid by increasing the Liquidation Preference of the Series A Preferred Stock for a period of sixteen dividend payment periods from the initial issuance date. See “ Note 12. Series A Preferred Stock ” for further details. Accumulated Other Comprehensive Income (Loss) Comprehensive income (loss) consists of two elements, net income (loss) and other comprehensive income (loss). Other comprehensive income (loss) items are recorded in the stockholders’ equity section on our consolidated balance sheets and excluded from net income (loss). Other comprehensive income (loss) consists primarily of foreign currency translation adjustments for subsidiaries with functional currencies other than the USD, unrealized translation gains (losses) on intercompany loans with foreign subsidiaries, and unrealized gains (losses) on interest rate swaps. 91 The following table shows the ending balance of the components of accumulated other comprehensive loss, net of income taxes, in the stockholders’ equity section on our consolidated balance sheets at the dates indicated (in thousands): December 31, 2022 2021 Other comprehensive income (loss) Foreign currency translation adjustment $ ( 22,632 ) $ ( 5,657 ) Unrealized translation gain on intercompany loans with foreign subsidiaries ( 7,426 ) 2,552 Unrealized gain (loss) on interest rate swaps 41,168 ( 8,409 ) Total accumulated other comprehensive income (loss) $ 11,110 $ ( 11,514 ) The Unrealized translation gain on intercompany loans with foreign subsidiaries as of December 31, 2022 is net of unrealized income tax expense of $ 0.4 million. The income tax expense (benefit) allocated to each component of other comprehensive income (loss) for all other periods and components was not material. Stock Compensation Plans The Company maintains two stock-based compensation plans, the 2010 Stock Option Plan (the “2010 Plan”) and the 2014 Stock Option Plan (the “2014 Plan”), which are described below. 2010 Plan At December 31, 2022, there were 32,346 options outstanding under the 2010 Plan. Following the effectiveness of the Company’s 2014 Plan in November 2014, no further awards have been made under the 2010 Plan, although each option previously granted under the 2010 Plan will remain outstanding subject to its terms. Any such shares of common stock that are subject to awards under the 2010 Plan which are forfeited or lapse unexercised and would otherwise have been returned to the share reserve under the 2010 Plan instead will be available for issuance under the 2014 Plan. 2014 Plan In November 2014, the Company adopted the 2014 Plan, providing for the granting of incentive stock options, as defined by the Internal Revenue Code, to employees and for the grant of non-statutory stock options, stock appreciation rights, restricted stock, restricted stock units, performance units and performance shares to employees, directors and consultants. The 2014 Plan also provides for the automatic grant of option awards to our non-employee directors. As of December 31, 2022, there were 121,975 options outstanding under the 2014 Plan, and shares of common stock reserved for issuance under the 2014 Plan consist of 631,776 shares. In addition, the number of shares available for issuance under the 2014 Plan will be increased annually in an amount equal to the least of (i) 4 % of the outstanding Shares on the last day of the immediately preceding Fiscal Year or (ii) such number of Shares determined by the Board. At December 31, 2022, there were 1,509,273 restricted stock units and 93,750 performance based restricted stock units outstanding under the 2014 Plan. Under both the 2010 Plan and 2014 Plan, options granted to date generally vest over a three or four year period, with a maximum term of ten years . The Company also grants restricted stock awards (“RSAs”) which generally vest over a three or four year period. Shares issued upon any stock option exercise and restricted under the 2010 Plan or 2014 Plan will be issued from the Company's authorized but unissued shares. 92 Share-based Compensation The Company recognized share-based compensation expense from all awards in the following expense categories (in thousands): Year Ended December 31, 2022 2021 2020 Cost of revenue $ 1,984 $ 2,088 $ 1,951 Research and development 2,733 3,085 3,391 Sales and marketing 4,239 5,957 3,450 General and administrative (1) 32,646 42,743 32,900 Total $ 41,602 $ 53,873 $ 41,692 (1) For the year ended December 31, 2021, a former executive resigned from his positions that resulted in stock-based compensation of $ 6.3 million related to the acceleration and deemed modification of the unvested portion of grants held at the time of transition. In accordance with ASC 718, Compensation—Stock Compensation , the fair value of these awards were modified and all related expense accelerated on the date of modification as a result of the reduction in required service. Our income tax benefits recognized from stock-based compensation arrangements in each of the periods presented were immaterial due to cumulative losses and valuation allowances. Restricted Stock Units (“RSU”) During the year ended December 31, 2022 the Company granted restricted stock units under its 2014 Stock Incentive Plan, in lieu of restricted stock awards, primarily for stock plan administrative purposes. Performance-Based Restricted Stock Units (“PRSU”) In 2022 and 2021, fifty percent of the awards granted to our Chief Executive Officer were PRSUs. The 2022 and 2021 PRSU agreements provide that the quantity of units subject to vesting may range from 0% to 300% of the units granted per the table below based on the Company's absolute total shareholder return (“TSR”) at the end of the eighteen month performance periods. At the end of the performance period, the 2021 PRSU resulted in no units granted. The following table summarizes PRSU and RSU activity during the year ended December 31, 2022 : Number of Units Weighted-Average Grant Date Fair Value Unvested restricted units outstanding as of December 31, 2021 1,443,284 $ 45.77 Granted 2,126,263 17.40 Vested ( 1,216,128 ) 36.29 Forfeited (1) ( 750,396 ) 32.99 Unvested restricted units outstanding as of December 31, 2022 1,603,023 $ 21.33 (1) Includes forfeited awards related to the 2021 PRSUs. At June 30, 2022, or the end of the performance period for the 2021 PRSUs, none of the awards vested. The total fair value of the RSUs vested during the years ended December 31, 2022, 2021 and 2020 was approximately $ 13.9 million, $ 28.2 million and $ 31.0 million, respectively. As of December 31, 2022, $ 29.5 million of unrecognized compensation cost related to unvested restricted stock awards and restricted stock units (including performance based awards) is expected to be recognized over a weighted-average period of 1.1 years. The PRSU and RSU activity table above includes PRSU units granted that are based on a 100 % target payout. Compensation expense is recognized over the required service period of the grant. The fair value of the RSUs is determined based on the grant date fair value of the award. The fair value of the PRSUs is determined using the Monte Carlo simulation model and is not subject to fluctuation due to achievement of the underlying market-based target. 93 The total fair value of PRSUs vested during the years ended December 31, 2022, 2021 and 2020 was $ 0.0 million , $ 5.6 million and $ 0.0 million , respectively. Significant assumptions used in the Monte Carlo simulation model for the PRSUs granted during the year ended December 31, 2022 and year ended December 31, 2021 are as follows: December 31, 2022 December 31, 2021 Expected volatility 49.5 % 53.6 % Risk-free interest rate 0.7 % 0.1 % Remaining performance period (in years) 1.46 1.35 Dividend yield — — Stock Option Activity Stock option activity during the year ended December 31, 2022 is as follows: Number of Options Outstanding Weighted– Average Exercise Price Weighted– Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in thousands) Outstanding at December 31, 2021 227,605 $ 9.15 Options exercised ( 44,382 ) 4.32 Options forfeited ( 28,226 ) 5.81 Options expired ( 676 ) 1.25 Outstanding at December 31, 2022 154,321 $ 11.19 3.31 $ 27 Options vested and expected to vest at December 31, 2022 154,321 $ 11.19 3.31 $ 27 Options vested and exercisable at December 31, 2022 154,321 $ 11.19 3.31 $ 27 The aggregate intrinsic value of options exercised at December 31, 2022, 2021 and 2020, was approximately $ 0.6 million, $ 1.1 million and $ 2.3 million, respectively. All of the Company’s outstanding stock options were fully vested as of December 31, 2019. As of December 31, 2022, there was no remaining unrecognized compensation cost related to stock options. The Company received approximately $ 0.2 million in cash from option exercises under the respective Plans in 2022. The Company issued shares from amounts reserved under the respective Plans upon the exercise of these stock options. The Company does not currently expect to repurchase shares from any source to satisfy such obligation under any of the Company’s stock option Plans. 14. Revenue Recognition Revenue Recognition Policy Revenue is recognized when control of the promised goods or services is transferred to the Company's customers, in an amount that reflects the consideration the Company expects to be entitled to in exchange for those goods or services over the term of the agreement, generally when made available to the customers. We enter into contracts that can include various combinations of products and services, which are generally capable of being distinct and accounted for as separate performance obligations. Revenue is recognized net of sales credits and allowances. Revenue is recognized net of any taxes collected from customers, which are subsequently remitted to governmental authorities. Revenue is recognized based on the following five step model in accordance with ASC 606, Revenue from Contracts with Customers : • Identification of the contract with a customer • Identification of the performance obligations in the contract • Determination of the transaction price • Allocation of the transaction price to the performance obligations in the contract 94 • Recognition of revenue when, or as, the Company satisfies a performance obligation Performance obligations under our contracts consist of subscription and support, perpetual licenses, and professional services revenue within a single operating segment. Subscription and Support Revenue The Company's software solutions are available for use as hosted application arrangements under subscription fee agreements without licensing perpetual rights to the software. Subscription fees from these applications are recognized over time on a ratable basis over the customer agreement term beginning on the date the Company's solution is made available to the customer. As our customers have access to use our solutions over the term of the contract agreement we believe this method of revenue recognition provides a faithful depiction of the transfer of services provided. Our subscription contracts are generally 1 to 3 years in length. Amounts that have been invoiced are recorded in accounts receivable and deferred revenue or subscription and support revenue, depending on whether the revenue recognition criteria have been met. Additional fees for monthly usage above the levels included in the standard subscription fee are recognized as subscription and support revenue at the end of each month and is invoiced concurrently. Subscription and support revenue includes revenue related to the Company’s digital engagement application which provides short code connectivity for its two-way short message service (“SMS”) programs and campaigns. As discussed further in the “ — Principal vs. Agent Considerations ” section below, the Company recognizes revenue related to these messaging-related subscription contracts on a gross basis. Perpetual License Revenue The Company also records revenue from the sales of proprietary software products under perpetual licenses. Revenue from distinct on-premises licenses is recognized upfront at the point in time when the software is made available to the customer. The Company’s products do not require significant customization. Professional Services Revenue Professional services provided with subscription and support licenses and perpetual licenses consist of implementation fees, data extraction, configuration, and training. The Company’s implementation and configuration services do not involve significant customization of the software and are not considered essential to the functionality. Revenue from professional services are recognized over time as such services are performed. Revenue for fixed price services are generally recognized over time applying input methods to estimate progress to completion. Revenue for consumption-based services are generally recognized as the services are performed. Significant Judgments Performance Obligations and Standalone Selling Price A performance obligation is a promise in a contract to transfer a distinct good or service to the customer and is the unit of accounting. Determining whether products and services are considered distinct performance obligations that should be accounted for separately versus together may require significant judgment. The Company has contracts with customers that often include multiple performance obligations, usually including professional services sold with either individual or multiple subscriptions or perpetual licenses. For these contracts, the Company records individual performance obligations separately if they are distinct by allocating the contract's total transaction price to each performance obligation in an amount based on the relative standalone selling price (“SSP”) of each distinct good or service in the contract. We only include estimated amounts of variable consideration in the transaction price to the extent it is probable that a significant reversal of cumulative revenue recognized will not occur when the uncertainty associated with the variable consideration is resolved. Judgment is required to determine the SSP for each distinct performance obligation. A residual approach is only applied in limited circumstances when a particular performance obligation has highly variable and uncertain SSP and is bundled with other performance obligations that have observable SSP. A contract's transaction price is allocated to each distinct performance obligation and recognized as revenue when, or as, the performance obligation is satisfied. We determine the SSP based on our overall pricing objectives, taking into consideration market conditions and other factors, including the value of our contracts, historical standalone sales, customer demographics, geographic locations, and the number and types of users within our contracts. 95 Principal vs. Agent Considerations The Company evaluates whether it is the principal (i.e., report revenues on a gross basis) or agent (i.e., report revenues on a net basis) for vendor reseller agreements and messaging-related subscription agreements. Where the Company is the principal, it first obtains control of the inputs to the specific good or service and directs their use to create the combined output. The Company's control is evidenced by its involvement in the integration of the good or service on its platform before it is transferred to its customers, and is further supported by the Company being primarily responsible to its customers and having a level of discretion in establishing pricing. While none of the factors individually are considered presumptive or determinative, in reaching conclusions on gross versus net revenue recognition, the Company places the most weight on the analysis of whether or not it is the primary obligor in the arrangement. Generally, the Company reports revenue from vendor reseller agreements on a gross basis, meaning the amounts billed to customers are recorded as revenue, and expenses incurred are recorded as cost of revenue. As the Company is primarily obligated in its messaging-related subscription contracts, has latitude in establishing prices associated with its messaging program management services, is responsible for fulfillment of the transaction, and has credit risk, we have concluded it is appropriate to record revenue on a gross basis with related pass-through telecom messaging costs incurred from third parties recorded as cost of revenue. Revenue provided from agreements in which the Company is an agent are immaterial. Contract Balances The timing of revenue recognition, billings and cash collections can result in billed accounts receivable, unbilled receivables, and deferred revenue. Billings scheduled to occur after the performance obligation has been satisfied and revenue recognition has occurred result in unbilled receivables, which are expected to be billed during the succeeding twelve-month period and are recorded in Unbilled receivables in our consolidated balance sheets. A contract liability results when we receive prepayments or deposits from customers in advance for implementation, maintenance and other services, as well as subscription fees. Customer prepayments are generally applied against invoices issued to customers when services are performed and billed. We recognize contract liabilities as revenue upon satisfaction of the underlying performance obligations. Contract liabilities that are expected to be recognized as revenue during the succeeding twelve-month period are recorded in Deferred revenue and the remaining portion is recorded in Deferred revenue, noncurrent on the accompanying consolidated balance sheets at the end of each reporting period. Deferred revenue primarily consist of amounts that have been billed to or received from customers in advance of revenue recognition and prepayments received from customers in advance for maintenance and other services, as well as initial subscription fees. We recognize deferred revenue as revenue when the services are performed, and the corresponding revenue recognition criteria are met. Customer prepayments are generally applied against invoices issued to customers when services are performed and billed. Our payment terms vary by the type and location of our customer and the products or services offered. The term between invoicing and when payment is due is not significant. For certain products or services and customer types, we require payment before the products or services are delivered to the customer. Unbilled Receivables Unbilled receivables represent amounts for which the Company has recognized revenue, pursuant to its revenue recognition policy, for software licenses already delivered and professional services already performed, but invoiced in arrears and for which the Company believes it has an unconditional right to payment. As of December 31, 2022 and 2021 unbilled receivables were $ 5.3 million and $ 4.8 million, respectively. 96 Deferred Commissions Sales commissions earned by our sales force, and related payroll taxes, are considered incremental and recoverable costs of obtaining a contract with a customer. Deferred commissions and other costs for new customer contracts are capitalized upon contract signing and amortized on a systematic basis that is consistent with the transfer of goods and services over the expected life of the customer relationships, which has been determined to be approximately 6 years. The expected life of our customer relationships is based on historical data and management estimates, including estimated renewal terms and the useful life of the associated underlying technology. Commissions paid on renewal contracts are not commensurate with commissions paid on new customer contracts, as such, deferred commissions related to renewals are capitalized and amortized over the estimated contractual renewal term of 18 months. We utilized the 'portfolio approach' practical expedient, which allows entities to apply the guidance to a portfolio of contracts with similar characteristics as the effects on the financial statements of this approach would not differ materially from applying the guidance to individual contracts. The portion of capitalized costs expected to be amortized during the succeeding twelve-month period is recorded as Deferred commissions, current, and the remainder is recorded as Deferred commissions, noncurrent, in our consolidated balance sheets. Amortization expense is included in sales and marketing expenses on our consolidated statements of operations. Deferred commissions are reviewed for impairment whenever events or circumstances indicate their carrying value may not be recoverable consistent with the Company's long-lived assets policy as described in “ Note 2. Basis of Presentation and Summary of Significant Accounting Policies ”. No indicators of impairment of deferred commissions were identified during the year ended December 31, 2022. The following table presents the activity impacting deferred commissions for the year ended December 31, 2022 (in thousands): Deferred Commissions Deferred commissions balance at December 31, 2021 $ 24,632 Capitalized deferred commissions 12,051 Amortization of deferred commissions ( 11,928 ) Deferred commissions balance at December 31, 2022 $ 24,755 Commissions capitalized in excess of amortization of deferred commissions for the year ended December 31, 2022 were $ 0.1 million. Deferred Revenue Deferred revenue represents either customer advance payments or billings for which the aforementioned revenue recognition criteria have not yet been met. Deferred revenue is mainly unearned revenue related to subscription services and support services. During the year ended December 31, 2022, we recognized $ 98.3 million and $ 3.0 million of subscription services and professional services revenue, respectively, that was included in the deferred revenue balances at the beginning of the period. In addition, during the year ended December 31, 2022 we recognized $ 10.9 million in revenue that was included in the acquired deferred revenue balance of our 2022 acquisitions as disclosed in “ Note 3. Acquisitions ”. Remaining Performance Obligations As of December 31, 2022, approximately $ 272.5 million of revenue is expected to be recognized from remaining performance obligations. We expect to recognize revenue on approximately 69 % of these remaining performance obligations over the next 12 months, with the balance recognized thereafter. Disaggregated Revenue The Company disaggregates revenue from contracts with customers by geography and revenue generating activity, as it believes it best depicts how the nature, amount, timing and uncertainty of revenue and cash flows are affected by economic factors. 97 Revenue by geography is based on the ship-to address of the customer, which is intended to approximate where the customers' users are located. The ship-to country is generally the same as the billing country. The Company has operations primarily in the U.S., United Kingdom and Canada. Information about these operations is presented below (in thousands): Year Ended December 31, 2022 2021 2020 Revenues: Subscription and support: United States $ 211,440 $ 205,882 $ 206,320 United Kingdom 41,728 45,673 39,032 Canada 17,304 13,870 14,830 Other International 27,415 22,196 17,322 Total subscription and support revenue 297,887 287,621 277,504 Perpetual license: United States 3,284 1,840 1,396 United Kingdom 425 11 16 Canada 264 109 76 Other International 2,975 190 396 Total perpetual license revenue 6,948 2,150 1,884 Professional services: United States 6,871 8,104 8,721 United Kingdom 2,269 2,666 2,059 Canada 947 410 504 Other International 2,381 1,065 1,106 Total professional service revenue 12,468 12,245 12,390 Total revenue $ 317,303 $ 302,016 $ 291,778 15. Employee Benefit Plans The Company has established various international defined contribution plans and one voluntary defined contribution retirement plan qualifying under Section 401(k) of the Internal Revenue Code. The Company made no material contributions to the 401(k) plans for the years ended December 31, 2022, 2021 and 2020. 16. Segment and Geographic Information ASC 280, Segment Reporting , establishes standards for reporting information about operating segments. It defines operating segments as components of an enterprise about which separate financial information is available that is evaluated regularly by the chief operating decision-maker (“CODM”) in deciding how to allocate resources and in assessing performance. Our Chief Executive Officer is considered to be our CODM. Our CODM manages the business as a multi-product business that utilizes its model to deliver software products to customers regardless of their geography or IT environment. Operating results are reviewed by the CODM primarily at the consolidated entity level, with the exception of recurring product level revenue, for purposes of making resource allocation decisions and for evaluating financial performance. Accordingly, we considered ourselves to be in a single operating and reporting segment structure. 98 Revenue See “ Note 14 Revenue Recognition—Disaggregated Revenue ” for a detail of revenue by geography. Identifiable Long-Lived Assets December 31, 2022 2021 Identifiable long-lived assets: United States $ 879 $ 1,367 United Kingdom 252 533 Canada 390 536 Other International 309 231 Total identifiable long-lived assets $ 1,830 $ 2,667 17. Related Party Transactions The Company does not have any material related party transactions to report for the year ended December 31, 2022. We are a party to two agreements, as detailed below, with companies controlled by ESW Capital LLC (“ESW”), a non-management investor in the Company which historically held more than 5 % of the Company's capital stock. As of July 9, 2021, ESW’s ownership in Upland was reduced to 4.8 % at which point DevFactory and Crossover (as hereinafter defined) were no longer considered related parties. • On March 28, 2017, the Company and DevFactory FZ-LLC (“DevFactory”) executed an amendment to the agreement to extend the initial term to December 31, 2021. Additionally, the Company amended the option for either party to renew annually for one additional year. The effective date of the amendment was January 1, 2017. During the years ended December 31, 2021 and 2020, the Company purchased software development services pursuant to a technology services agreement with DevFactory, in the amount of $ 9.6 million and $ 7.4 million, respectively. At December 31, 2021, amounts included in accounts payable owed to this company totaled $ 0.0 million . • The Company purchased services from Crossover, Inc. (“Crossover”), a company controlled by ESW Capital, LLC (a non-management investor) of approximately $ 4.0 million and $ 4.8 million during the years ended December 31, 2021 and 2020. Crossover provides a proprietary technology system to help the Company identify, screen, select, assign, and connect with necessary resources from time to time to perform technology software development and other services throughout the Company, and track productivity of such resources. As of December 31, 2021, amounts included in accounts payable and accrued liabilities owed to this company totaled $ 0.9 million. 18. Subsequent Events On February 21, 2023, the Company entered into that certain Amendment No.1 to the Credit Facility (the “Amendment”), which amends the Credit Facility. The Amendment amended the interest rate benchmark from the LIBOR to SOFR. Other than the foregoing, the material terms of the Credit Agreement remain unchanged. 99 Item 9. Changes in and Disagreements with Accountants on Accounting and Financial Disclosure None.