Upland Software, Inc. (NASDAQ:UPLD) (the "Company"), a leader in AI-powered knowledge and content management software, today announced that Sean Nathaniel has commenced his tenure as the Company's President and Chief Executive Officer. As part of Mr. Nathaniel's compensation package, the Company will grant two inducement equity awards to Sean Nathaniel pursuant to the terms of Mr. Nathaniel's previously disclosed offer letter dated February 21, 2026. The inducement awards will be granted as an inducement material to Mr. Nathaniel entering into employment with the Company in accordance with Nasdaq Listing Rule 5635(c)(4).

The inducement awards will consist of an award of performance-based restricted stock units ("PRSUs") relating to up to 500,000 shares of Company's common stock that will vest, if at all, at the end of a three-year vesting period subject to certain performance goals and an award of restricted stock units ("RSUs") relating to 500,000 shares of Company's common stock that will vest in 12 equal quarterly installments. In each case, vesting of the PRSUs and RSUs is subject to Mr. Nathaniel's continuous employment through the applicable vesting date or earlier vesting due to a change of control and certain termination events. The grant date for the inducement awards will be on or about June 5, 2026.

About Upland Software

Upland Software, Inc. (NASDAQ:UPLD) is a leader in AI-powered knowledge and content management software. Upland's solutions help enterprises unlock critical knowledge, automate content workflows, and drive measurable ROI — enhancing customer and employee experiences while supporting regulatory compliance. More than 1,100 enterprise customers rely on Upland to solve complex challenges and provide a trusted path for AI adoption. For more information, visit www.uplandsoftware.com.

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Investor Relations Contact:

Michael D. Hill

512-960-1031

investor-relations@uplandsoftware.com

Media Contact:

Lloyd Berry

512-960-1010

media@uplandsoftware.com

Upland Announces Commencement of New CEO Tenure and Inducement Awards