Upland Software Taps Jennifer Simon as CFO to Succeed Retiring Mike Hill
UPLD sits 17% above its 52-week low of $4 on light trading volume (0.2× avg).
Summary
Effective August 17, 2026, Upland Software appointed Jennifer Simon as CFO, succeeding retiring CFO Mike Hill. Simon brings extensive software finance experience and will receive a compensation package including $350,000 base salary, bonus, and equity grants.
Key Events · Executive and Board Changes · UPLD
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New CFO Appointed
Effective August 17, 2026, Jennifer Simon steps into the CFO role, succeeding retiring CFO Michael D. Hill.
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Compensation Terms
Simon's package includes a $350,000 base salary, a 75% annual bonus target, 30,000 RSUs vesting over 3 years, and up to 25,000 performance-based RSUs.
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Leadership Background
With over 20 years of finance leadership in software and private equity-backed companies, Simon previously served as SVP Finance at NextGen Healthcare and interim CFO at Quest Software.
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Strategic Context
The appointment arrives as Upland sharpens its focus on AI-driven product innovation and balance sheet strengthening under new CEO Sean Nathaniel.
Analysis · UPLD · Technology
Filling the vacancy left by Mike Hill's retirement, Upland Software has appointed Jennifer Simon as its new CFO, effective August 17, 2026. Simon brings over 20 years of finance leadership, most recently serving as SVP Finance at NextGen Healthcare and previously as interim CFO at Quest Software. Her compensation package includes a $350,000 base salary, a 75% bonus target, 30,000 restricted stock units vesting over three years, and performance-based RSUs. This hire completes the CFO transition announced on July 7 and adds a seasoned executive to the leadership team as the company sharpens its strategic focus on AI-driven product innovation and balance sheet strengthening.
At the time of this filing, UPLD was trading at $4.69 on NASDAQ in the Technology sector, with a market capitalization of approximately $13.8M. The 52-week trading range was $4.00 to $39.10. This filing was assessed with neutral market sentiment and an importance score of 7 out of 10.