CFO THOUGHT LEADER

What's Rarely Measured Matters Most

CFO THOUGHT LEADER is a general podcast hosted by CFO THOUGHT LEADER, with 10 episodes on record and a Required Pod Score of 80.

CFO THOUGHT LEADER hosts CFO THOUGHT LEADER, a general show with 10 episodes published.

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  CFO THOUGHT LEADER

  Why AI Shouldn’t Be Priced by the Token | Ken Stillwell, CFO, Pegasystems

  Sep 30, 2026—

  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, […] The post Why AI Shouldn’t Be Priced by the Token | Ken Stillwell, CFO, Pegasystems appeared first on CFO THOUGHT LEADER .

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  CFO THOUGHT LEADER

  1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems

  Sep 30, 202649 min

  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 […] The post 1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems appeared first on CFO THOUGHT LEADER .

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  When Focus Raises the Execution Bar | Brittany Cerwin, CFO, Middleby

  Sep 29, 2026—

  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 […] The post When Focus Raises the Execution Bar | Brittany Cerwin, CFO, Middleby appeared first on CFO THOUGHT LEADER .

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  CFO THOUGHT LEADER

  2017: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation

  Sep 28, 202641 min

  For years, Middleby executives arriving at investor conferences faced a storytelling problem: 30 minutes wasn’t much time to explain three different businesses, each with its own brands, markets, investments, and stage of development. Today, CFO Brittany Cerwin has a different story to tell. Over the past 18 months, Middleby separated its food-processing business into a […] The post 2017: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation appeared first on CFO THOUGHT LEADER .

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  CFO THOUGHT LEADER

  Where Automation Meets Financial Discipline | Ryan Raccon, CFO, Zapier

  Sep 23, 2026—

  In this episode, Jack is joined by Ryan Roccon, CFO and COO of Zapier. They discuss how Zapier’s automation platform is adapting to an AI environment in which companies can build applications and agents quickly but still need reliability, visibility, permissions, auditability, and cost control when those workflows move into production. Roccon explains how Zapier […] The post Where Automation Meets Financial Discipline | Ryan Raccon, CFO, Zapier appeared first on CFO THOUGHT LEADER .

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