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, […]
When Focus Raises the Execution Bar | Brittany Cerwin, CFO, Middleby
In this episode, Jack is joined by Brittany Cerwin, CFO of Middleby. After years operating across commercial foodservice, food processing, and residential kitchen equipment, Middleby has reshaped its portfolio around its commercial business. Cerwin explains why that focus creates a clearer capital allocation story—and places greater attention on execution. The discussion moves inside Middleby’s growth […]
1197: The CFO Who Learned Finance by Owning Sales | Sinohe Terrero, CFO, Envoy
Bringing a Cross-Functional Approach to Scenario Analysis | Betsy Ward, CFO, MassMutual
Ward: I actually think it might be more unique given my background to talk about a Strategic Finance moment that related to a position I was in when I was in, in actually Investment Management, which relates to those scenarios I was talking about. So while I was working in mass, Mutual’s Investment Management subsidiary, […]



