Upland Software, Inc.

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers. Retirement of Michael D. Hill as Chief Financial Officer On June 30, 2026, Michael D. Hill, Chief Financial Officer of Upland Software, Inc. (the “Company”) notified the board of directors of the Company (the “Board”) of his intention to retire as Chief Financial Officer, effective July 27, 2026 (the “Effective Date”). The Board has initiated a search process to identify Mr. Hill’s successor. Mr. Hill’s decision to retire was not the result of any disagreements with the Company on any matter relating to the Company’s operations, policies or practices. Appointment of David Tamez as Interim Chief Financial Officer On July 6, 2026, the Board appointed David Tamez to serve as the interim Chief Financial Officer of the Company, effective as of the Effective Date, until a permanent successor is identified. Mr. Tamez, age 62, has served as Senior Vice President, Treasury Management of the Company since June 2023. Prior to that, Mr. Tamez served as Vice President, Accounting and Corporate Controller of the Company from 2014 to 2023. Before joining the Company, Mr. Tamez served as Vice President, Finance for a division of Callaway Golf (NYSE: CALY), the e-commerce arm for all direct to consumer sales for Callaway golf equipment, from September 2003 to February 2011, and in other finance and accounting roles for companies in Austin, Texas. Mr. Tamez started his career with BDO USA, LLP in the Audit and Assurance practice, from 1989 to 1997. Mr. Tamez holds a B.B.A. in Accounting from the University of Texas at Austin. As of the filing of this Current Report on Form 8-K, the Compensation Committee of the Board and the Board have not finalized the compensation of Mr. Tamez in connection with his appointment as interim Chief Financial Officer. The Company will provide this information by filing an amendment to this Current Report on Form 8-K after the information is determined or becomes available. In connection with Mr. Tamez’s appointment, Mr. Tamez and the Company entered into an indemnification agreement substantially similar to the indemnification agreement that the Company’s directors and executive officers have entered, the form of which is on file with the U.S. Securities and Exchange Commission. No family relationships exist between Mr. Tamez and any of the Company’s directors or executive officers or any person nominated or chosen by the Company to become a director or executive officer. There are no arrangements or understandings between Mr. Tamez and any other person pursuant to which Mr. Tamez was selected as interim Chief Financial Officer of the Company, nor are there any transactions to which the Company is or was a participant and in which Mr. Tamez has or had a direct or indirect material interest subject to disclosure under Item 404(a) of Regulation S-K.