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FORM 10-K ☒ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December31, 2025OR☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specified in its charter) (Address, including zip code, and telephone number, including area code, of registrant’s principal executive offices) Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule 405 of the Securities Act.YesNo Indicate by check mark if the registrant is not required to file reports pursuant to Section13 or Section15(d) of the Act.YesNo Indicate by check mark whether the registrant (1)has filed all reports required to be filed by Section13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for suchshorter period that the registrant was required to file such reports), and (2)has been subject to such filing requirements for the past 90 days.YesNo Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§ 232.405 of this chapter)during the preceding 12 months (or for such shorter period that the registrant was required to submit and post such files).YesNo Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitionsof “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act. Large accelerated filerNon-accelerated filer If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standardsprovided pursuant to Section 13(a) of the Exchange Act.☐ Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of its internal control over financial reporting under Section404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accounting firm that prepared or issued its audit report.☐ If securities are registered pursuant to Section 12(b) of the Act, indicate by check mark whether the financial statements of the registrant included in the filing reflect the correction of an error topreviously issued financial statements.☐ Indicate by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensation received by any of the registrant’s executive officersduring the relevant recovery period pursuant to § 240.10D-1(b).☐ Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act).Yes☐No The aggregate market value of the registrant’s common stock held by non-affiliates of the registrant was approximately $47.8 million based upon the closing price of $1.95 of suchcommon stock on the Nasdaq Global Market on June30, 2025 (the last business day of the registrant’s most recently completed second fiscal quarter). Shares of common stock held as ofJune30, 2025 by each director and executive officer of the registrant, as well as shares held by each holder of 10% of the common stock known to the registrant, have been excluded forpurposes of the foregoing calculation. This determination of affiliate status is not a conclusive determination for other purposes. As of March2, 2026, 29,118,178 shares of the registrant’s Common Stock were outstanding. Certain portions, as expressly described in this Annual Report on Form 10-K, of the registrant’s Proxy Statement for the 2026 Annual Meeting of the Stockholders, to be filed not later than120 days after the end of the year covered by this Annual Report, are incorporated by reference into Part III of this Annual Report where indicated. TABLE OF CONTENTS PART I Item1.Item1A.Item1B.Item 1C.Item2.Item3.Item4. BusinessRisk FactorsUnresolved Staff CommentsCybersecurityPropertiesLegal ProceedingsMine Safety Disclosures PARTIIItem5.Item6.Item7.Item7A.Item 8. Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities[Reserved]Management’s Discussion and Analysis of Financial Condition and Results of OperationsQuantitative and Qualitative Disclosures about Market RiskFinancial Statements and Supplementary DataReport of Independent Registered Public Accounting FirmConsolidated Financial StatementsConsolidated Balance SheetsConsolidated Statements of OperationsConsolidated Statements of Comprehensive LossConsolidated Statements ofEquity (Deficit)Consolidated Statements of Cash FlowsNotes to the Consolidated Financial StatementsChanges in and Disagreements with Accountants