In this episode, Jack is joined by Ken Stillwell, CFO of Pegasystems. Stillwell describes a finance career shaped early by M&A, operating responsibility, and the realization that financial results are ultimately reflections of what is happening inside the business. His prescription for becoming a more strategic CFO is practical: spend time with customers, sales teams, product leaders, and operations until finance becomes a partner others actively want in the room.
That operating perspective surfaces throughout the discussion of Pegasystems’ cloud transition, customer-expansion model, and evolving software economics. Stillwell explains why customer adoption can reveal more than reported results, why the company resisted token-based AI pricing, and how disciplined investments helped improve cloud margins. He also shares how Rule 40 became more than a finance metric at Pegasystems, influencing how employees think about growth, costs, and investment—and why humility and genuine care remain central to his own leadership philosophy.
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