Ken Stillwell

Chief Operating Officer & Chief Financial Officer Pegasystems

Last Reviewed: September 18, 2026

Executive Summary

Ken Stillwell is Chief Operating Officer and Chief Financial Officer of Pegasystems, holding both roles at once — an arrangement that is unusual at a company of Pega’s size and that reflects what the job has actually involved. Pegasystems sells enterprise decisioning and workflow automation software to banks, insurers, telecoms and governments, and over the past decade it has undertaken the transition that defines the fortunes of every legacy enterprise software company: moving from perpetual licences recognised up front to cloud subscriptions recognised over time. That transition is simultaneously a financial problem, because reported revenue falls before it rises, and an operational one, because the company has to learn to run software on behalf of its customers rather than shipping it to them. Stillwell owns both halves. His remit covers finance, investor relations, legal, facilities, information technology, Pega Cloud and global client support, spanning more than a thousand employees, and Pega credits him as central to its shift to an as-a-service model.

Career Highlights

• Chief Operating Officer and Chief Financial Officer of Pegasystems, signing the company’s SEC filings in that dual capacity.
• Oversees finance, investor relations, legal, facilities, information technology, Pega Cloud, global client support and business operations across more than 1,000 employees worldwide.
• Credited by Pega as central to its transformation into an as-a-service business through a cloud-first strategy with multi-cloud deployment.
• Joined Pegasystems in July 2016 as Senior Vice President, Chief Financial Officer and Chief Administrative Officer; promoted to Chief Operating Officer in April 2021.
• Previously Senior Vice President and Chief Financial Officer at Dynatrace, the observability company.
• Previously Executive Vice President and Chief Financial Officer at Sovos, the tax and regulatory compliance software company.
• Spent five years as divisional Chief Financial Officer at PTC, covering its product lifecycle and application lifecycle management business.
• Certified Public Accountant with more than 25 years of financial leadership in high-growth technology organisations.
• Executive sponsor of the Veterans@Pega employee resource group.

Professional Journey

Stillwell trained in business and economics at the University of Pittsburgh, took a master’s in accounting and finance at the University of South Carolina, and qualified as a Certified Public Accountant. That combination — a technical accounting foundation rather than an investment-banking one — has shaped a career spent inside operating companies rather than advising them.

He spent five years at PTC as a divisional chief financial officer, responsible for the product lifecycle and application lifecycle management segment. Divisional CFO work at a company like PTC is close to the business: the segment has its own customers, its own cost base and its own margin problems, and the role is effectively that of a business finance lead rather than a corporate controller.

He then moved into full company CFO roles at two Massachusetts software businesses. At Sovos he was Executive Vice President and Chief Financial Officer, at a company selling tax and regulatory compliance software — a business of continuous regulatory content updates and subscription revenue. At Dynatrace he was Senior Vice President and Chief Financial Officer, in application performance monitoring, another subscription business built on continuous delivery.

Pegasystems recruited him in June 2016, announcing him as Chief Financial Officer and Chief Administrative Officer effective the following month. The administrative half of that title mattered: from the start his brief extended past the finance function into the company’s operating infrastructure. Over the following years Pega executed its shift to Pega Cloud, absorbing the revenue-recognition pain of moving customers from perpetual licences to subscriptions while simultaneously building the capability to operate its own software as a service on multiple public clouds.

In April 2021 Pega made him Chief Operating Officer alongside the CFO role. The combined portfolio now runs from investor relations and legal through to cloud operations and global client support. He continues to sign Pegasystems’ filings with the Securities and Exchange Commission as Chief Operating Officer and Chief Financial Officer, most recently on the company’s June 2026 report of its annual shareholder meeting.

Education

University of Pittsburgh

Bachelor of Science, Business and Economics

University of South Carolina

Master of Science, Accounting and Finance