Upland Software has announced the appointment of Jennifer Simon, CPA, as its new Chief Financial Officer, effective August 17, 2026. Simon will lead the company's global finance organization as Upland continues to strengthen its financial operations and advance its strategy around AI-powered enterprise intelligence.
Upland Software announced that Jennifer Simon will assume the role of Chief Financial Officer, reporting directly to President and Chief Executive Officer Sean Nathaniel.
Simon brings more than two decades of financial leadership experience across enterprise software, technology, and private equity-backed organizations. Most recently, she served as Senior Vice President of Finance at NextGen Healthcare.
Prior to that, she spent more than three years at Quest Software, where she advanced from Vice President of Finance to Interim Chief Financial Officer. During her tenure, she led initiatives that included significant cost optimization, recurring revenue reporting, merger and acquisition diligence, and debt restructuring.
Earlier in her career, Simon also served as Chief Financial Officer at Community Impact Newspaper, helping the organization expand its operations across multiple markets.
In her new position, Simon will oversee financial planning and analysis, accounting, treasury, tax, and investor relations while working closely with Upland's executive leadership team to strengthen financial discipline and support strategic decision-making.
Her appointment comes as Upland continues refining its focus on enterprise intelligence across knowledge, content, and data while investing in AI-powered product innovation and improving capital allocation.
"Since becoming CEO, my focus has been on sharpening our strategy, simplifying how we operate, and strengthening our leadership team," said Sean Nathaniel, President and Chief Executive Officer of Upland Software. "Jennifer's appointment marks an important milestone in that work. She brings significant software transformation experience, financial discipline, and a strong operating perspective. I look forward to partnering with her as we build a more focused and agile organization, thoughtfully apply AI across our products and operations, and strengthen business performance."
Throughout her career, Simon has led financial transformation initiatives across public and private software organizations.
Her experience includes:
Simon is a Certified Public Accountant and holds a Master's degree in Professional Accounting from the University of Texas at Austin.
"I am excited to join Upland at an important point in its transformation," said Jennifer Simon. "Upland has strong customer relationships, a portfolio of mission-critical products, and meaningful opportunities ahead. I look forward to partnering with Sean and the leadership team to strengthen execution and create long-term value for our customers and shareholders."
Jennifer Simon succeeds Mike Hill, one of Upland Software's founding executives, who will retire from his position as Chief Financial Officer after helping guide the company's financial strategy over many years.
According to the company, Hill worked closely with CEO Sean Nathaniel during the leadership transition, helping position Upland for its next phase of growth focused on AI-powered enterprise intelligence, operational efficiency, and long-term value creation.
Upland Software (Nasdaq: UPLD) provides an intelligence layer that unifies and contextualizes enterprise knowledge, content, and data, turning isolated information into actionable outcomes for every human and agent. More than 1,100 enterprise customers rely on Upland's deep domain expertise to drive measurable, value-add outcomes, unlocking the full potential of AI as their organizations evolve. For more information, visit www.uplandsoftware.com.
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