Upland Software Taps NextGen Healthcare Finance Chief as New CFO
Event summary
- Jennifer Simon, CPA, appointed as Upland Software's new Chief Financial Officer effective August 17, 2026.
- Simon brings over 20 years of finance leadership experience in software and private equity-backed environments.
- She previously drove $120M in cost savings at Quest Software and scaled Community Impact Newspaper from 20 to 41 markets.
- Simon succeeds Mike Hill, a founding team member who is retiring after an illustrious career with Upland.
The big picture
Upland Software's appointment of Jennifer Simon as CFO underscores its commitment to financial discipline and strategic focus amid a broader industry shift towards AI-driven enterprise solutions. With over $1B in revenue at Quest Software, Simon's experience in private equity-backed environments aligns with Upland's current priorities of disciplined capital allocation and balance sheet strengthening.
What we're watching
- Financial Discipline
- How Jennifer Simon's track record of cost savings and financial restructuring will impact Upland's balance sheet and operational efficiency.
- Strategic Focus
- Whether Upland can successfully sharpen its focus on core intelligence domains while investing in AI-driven product innovation.
- Leadership Transition
- The pace at which Simon can integrate into Upland's leadership team and support CEO Sean Nathaniel's strategic priorities.