In this episode, Jack is joined by Perry Beberman, CFO of Bread Financial. For a financial services company built around consumer credit and retail partnerships, growth is inseparable from decisions about risk, customer behavior, and the use of capital. Beberman explains how Bread Financial manages these competing considerations while reshaping its balance sheet, funding structure, […]
How Hippo Learned Which Risks to Keep | Guy Zeltser, CFO, Hippo Insurance
In this episode, Jack is joined by Guy Zeltser, CFO of Hippo Insurance. One of the more consequential decisions in Hippo’s recent history involved deliberately reducing the size of its homeowners insurance business. Following a difficult period in 2023, the company needed to rebalance its exposure to risk—even if that meant temporarily moving backward on […]
You Can’t Have Probably Right Revenue | Sam Chung, Chief Customer Officer, Salesforce
In this episode, Jack is joined by Sam Chung, Chief Customer Officer at Salesforce and former CFO of Salesforce.org. For finance leaders, the transition from subscription revenue to consumption-based and hybrid models introduces a fundamental challenge: the predictability that once made recurring revenue attractive can no longer be taken for granted. Chung brings an unusually […]
The Economics of Removing Friction | Tami Wilson-Ciranna, CFO, Curative
Curative’s transformation from pandemic testing to employer health insurance gives Wilson-Ciranna an unusual vantage point on growth, risk and operating finance. She explains why the company committed roughly $500 million to its insurance launch and how its zero-deductible, zero-copay model is designed to remove barriers that can discourage people from seeking preventive care or taking […]
Why AI Shouldn’t Be Priced by the Token | Ken Stillwell, CFO, Pegasystems
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 […]
Where Automation Meets Financial Discipline | Ryan Raccon, CFO, Zapier
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 […]
When Expertise Gives Way to Curiosity \ Jessica Sommers, CFO, Aledade
In this episode, Jack is joined by Jessica Somers, CFO of Aledade. They discuss how the company uses technology, data, and insights to help primary care practices succeed in value-based care, where improved patient outcomes can generate healthcare savings. Somers explains why Aledade takes a long-term approach to investment and how its proprietary technology platform […]
The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri
In this episode, Jack is joined by Jack Gordon, CFO of Harri, an AI-powered workforce operating system serving the hospitality industry. They discuss how Harri helps restaurant operators manage hiring, scheduling, labor, compliance, and employee engagement, and why Gordon views customer usage and satisfaction as important leading indicators of financial performance. The conversation explores AI-driven […]
The Best Trade You Don’t Make | Shiv Verma CFO Robin Hood
In this episode, Jack is joined by Shiv Verma, CFO of Robinhood. They discuss Robinhood’s evolution from commission-free brokerage to a financial super app and the revenue streams supporting equities, options, crypto, interest income, and subscriptions. Verma explains why net deposits serve as the company’s North Star and how finance evaluates customer pain points, unit […]
Strategy Lessons From McKinsey’s CFO | Yuval Atsmon, CFO, McKinsey & Company
After a failed military mission caused by one wrong GPS coordinate and later uncovering a flawed privatization pricing formula others dismissed, Yuval Atsmon learned a defining finance lesson: never accept numbers at face value. Great CFOs question assumptions, triangulate facts, and ensure teams understand the logic behind decisions. Now Watch Our Complete Episode Featuring CFO […]
Seeing The Business End-To-End | David Larson, CFO, Feedzai
At Thomson Reuters, David Larson repositioned a Hyderabad shared services team from transactional support to strategic finance talent, unlocking capacity for reinvestment. He built buy-in through listening, planning, and influence rather than authority. The initiative endured—and taught him that lasting change comes from changing minds, not issuing mandates. Now Watch our Complete Episode Featuring CFO […]