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, […]
1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems
When Pegasystems began building its cloud business, the economics were hardly what investors would expect from a mature software company. Cloud gross margin was below 30%, recalls CFO and COO Ken Stillwell. The destination was roughly 80%. Getting there, however, required accepting that the path would not be straight. At one point, Pega deliberately stepped…
Listen to the Episode Below (0:48:45)
1209: Finding a Larger Voice in the Room | Ross Grainger, CFO, Nasuni
Ross Grainger remembers an early chapter of his career when finance was only one part of the job. After stepping outside a traditional finance path to own and operate a Maako auto-body franchise, Grainger tells us he learned what it meant to “act like an owner.” That sometimes meant cleaning toilets, learning to paint cars,…
Listen to the Episode Below (0:33:12)
What Wall Street Taught One CFO About Strategy | Michael Perica, CFO, Rimini Street
Perica identifies AI as a turning point for the CFO role, prompting closer collaboration with CIOs and a shift toward enterprise-wide transformation. By moving beyond finance-only automation to broader operational impact, CFOs can now shape strategy, drive technology adoption, and position finance as a central force in organizational change. Now Watch Our Complete Episode Featuring […]