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 New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce
How consumption models, AI, and rising complexity are reshaping the CFO mandate Revenue models are becoming more complex—and for finance leaders, the consequences extend well beyond how a company bills its customers. As businesses combine subscriptions, consumption-based pricing, and other models, CFOs face new questions around predictability, visibility, cash flow, and the infrastructure needed to…
Listen to the Episode Below (0:50:19)
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 […]
1197: The CFO Who Learned Finance by Owning Sales | Sinohe Terrero, CFO, Envoy
Sinohe Terrero still remembers the timing. He joined Envoy in January, only to see the workplace transformed just two months later as offices around the world shut down because of COVID. The company had been building products for offices, but suddenly, almost no one was going to the office, Terrero tells us. That abrupt shift…
Listen to the Episode Below (0:45:27)
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, […]