Upland Software, Inc. 10-Q

Item 5. Other Information Rule 10b5-1 Trading Plans On March 9, 2026 , Timothy Mattox , who serves on the Company’s Board of Directors , adopted a written plan for the sale of up to 58,481 shares of the Company’s Common Stock that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c) under the Exchange Act. The written plan will expire on August 14, 2026 , or on any earlier date on which all of the shares have been sold. 28 Table of Contents During the three months ended March 31, 2026, none of our other officers (as defined in Rule 16a-1(f)) or directors adopted or terminated any Rule 10b5-1 trading arrangement or non-Rule 10b5-1 trading arrangement (as such terms are defined in Item 408 of Regulation S-K under the Securities Act). Item 6. Exhibits See the Exhibit Index immediately following this page, which is incorporated herein by reference. 29 Table of Contents EXHIBIT INDEX Exhibit Number Exhibit Description 10.1* Transition Agreement, dated February 25, 2026, by and between Upland Software, Inc. and John T. McDonald (incorporated by reference to the Company's Current Report on Form 8-K filed with the SEC on February 25, 2026). 10.2*+ Offer Letter, dated February 21, 2026, by and between Upland Software, Inc. and Sean Nathaniel 31.1* Certification of Chief Executive Officer pursuant to Exchange Act Rules 13a-14(a) and 15d-14(a), as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 31.2* Certification of Chief Financial Officer pursuant to Exchange Act Rules 13a-14(a) and 15d-14(a), as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 32.1** Certification of Chief Executive Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 32.2** Certification of Chief Financial Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 101* Inline XBRL (Extensible Business Reporting Language). The following materials from this Quarterly Report on Form 10-Q for the periods ended March 31, 2026, formatted in Inline XBRL: (i) condensed consolidated balance sheets of Upland Software, Inc., (ii) condensed consolidated statements of operations of Upland Software, Inc., (iii) condensed consolidated statements of comprehensive income (loss) of Upland Software, Inc., (iv) condensed consolidated statement of stockholders’ deficit of Upland Software, Inc., (v) condensed consolidated statements of cash flows of Upland Software, Inc. and (vi) notes to unaudited condensed consolidated financial statements of Upland Software, Inc. The instance document does not appear in the interactive data file because its XBRL tags are embedded within the Inline XBRL document. 104* Cover Page Interactive Data File (formatted as Inline XBRL and contained in Exhibit 101) * Filed herewith. ** Furnished herewith. + Certain personal information in this exhibit has been omitted in accordance with Regulation S-K Item 601(a)(6). 30 Table of Contents SIGNATURE Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized. UPLAND SOFTWARE, INC. Dated: May 1, 2026 /s/ Michael D. Hill Michael D. Hill Chief Financial Officer 31