COO, CFO
Kenneth Stillwell is the Chief Operating Officer (COO) and Chief Financial Officer (CFO) of Pegasystems Inc. (PEGA), a position he has held since joining the company in July 2016 as CFO and Chief Administrative Officer, with promotion to COO in April 2021.[[1]](https://fintool.com/app/research/companies/PEGA/people/kenneth-stillwell)[[2]](https://www.pega.com/about/news/press-releases/pegasystems-appoints-ken-stillwell-chief-financial-officer-and-chief)[[4]](https://www.pega.com/about/leadership/ken-stillwell) Age 54, Stillwell oversees finance, investor relations, legal, facilities, IT, Pega Cloud, global client support, and business operations, leading over 1,000 employees and driving Pega's shift to a cloud-first, as-a-Service model.[[1]](https://fintool.com/app/research/companies/PEGA/people/kenneth-stillwell)[[4]](https://www.pega.com/about/leadership/ken-stillwell) He recently engaged in insider trading, selling 2,000 shares on April 1, 2025, under a Rule 10b5-1 plan, retaining 21,245 shares post-transaction.[[3]](https://www.investing.com/news/insider-trading-news/pegasystems-coo-and-cfo-kenneth-stillwell-sells-139500-in-stock-93CH-3966863)
Stillwell brings over 25 years of financial leadership in high-growth tech firms, including Senior Vice President and CFO at Dynatrace (overseeing finance, HR, IT, legal), EVP and CFO at SOVOS (scaling SaaS operations), and Divisional CFO at PTC in PLM/ALM segments.[[1]](https://fintool.com/app/research/companies/PEGA/people/kenneth-stillwell)[[2]](https://www.pega.com/about/news/press-releases/pegasystems-appoints-ken-stillwell-chief-financial-officer-and-chief)[[4]](https://www.pega.com/about/leadership/ken-stillwell) He holds a B.S. in business/economics from the University of Pittsburgh, an M.S. in accounting and finance from the University of South Carolina, and is a Certified Public Accountant (CPA).[[1]](https://fintool.com/app/research/companies/PEGA/people/kenneth-stillwell)[[2]](https://www.pega.com/about/news/press-releases/pegasystems-appoints-ken-stillwell-chief-financial-officer-and-chief)
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