What's Rarely Measured Matters Most

finance transformation

1228: The New Economics of SolarWinds | Samuel Monti, CFO, SolarWinds

Sam Monti was working in finance at Rockwell Automation when a conversation about charging customers for technical support took an unexpected turn. A salesman suggested collecting a fee for access to the company's engineers. Monti had another idea: Why not make it a membership, like a country club? The resulting subscription business generated $150 million…
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1226: Anaplan’s Growth Equation: AI, Profitability, and Scale | Hemant Kapadia, CFO, Anaplan

For Anaplan CFO Hemant Kapadia, one of the more revealing measures of the company's transformation isn't revenue growth alone. It's the fact that Anaplan has nearly the same number of employees it had when it was taken private in 2022—even as annual recurring revenue has grown from approximately $600 million toward $1.4 billion. The company…
Listen to the Episode Below (0:59:39)
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Evan Goldberg on the End of ERP as We Know It

At SuiteWorld 2026, NetSuite's founder outlines how AI is transforming business software—and what the shift means for CFOs. When Evan Goldberg, founder and executive vice president of Oracle NetSuite, declares that ERP as we know it is over, the statement carries particular weight. Goldberg helped pioneer cloud-based enterprise software in 1998, challenging the conventional wisdom…
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1225: Nix the Clicks: Building a Finance Function That Manages by Exception | Steve Fox, CFO, Every Man Jack

When Steve Fox joined Every Man Jack in 2021, the men's personal care brand had a new private equity owner and an ambitious growth agenda. Carlyle Group saw an opportunity: a widely distributed brand that had never invested heavily in marketing. The challenge was finding the operating leverage to fund that investment. For Fox, the…
Listen to the Episode Below (0:29:24)
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1224: Building a Cybersecurity Leader for the AI Era | Joe Iantosca, CFO, Cyera

When Joe Iantosca arrived at Cyera as CFO, his first hire wasn't an accountant or an FP&A professional. It was a data engineer. For Iantosca, the decision reflected a conviction formed over years of working inside technology companies: Finance cannot help steer a business without reliable access to the information driving it. That conviction first…
Listen to the Episode Below (0:39:11)
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1223: Scaling Sokin: Beyond the First $100 Million | Tom Steer, CFO, Sokin

When Tom Steer joined Sokin as CFO, he already knew the international payments company unusually well. As an investment banker at FT Partners, he had advised Sokin through a capital raise during a difficult period for fintech funding. He knew its leadership, its financial projections, and the ambitions behind its growth. What he had yet…
Listen to the Episode Below (0:51:58)
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1221: Rebuilding Bread Financial’s Capital Foundation—And What It Made Possible | Perry Beberman, CFO, Bread Financial

When Perry Beberman arrived at what is now Bread Financial, the company had a balance sheet problem. It was carrying too much leverage, had insufficient capital, and needed a more disciplined approach to funding its lending business. For a finance executive who had spent decades navigating consumer credit cycles, the assignment was familiar territory. The…
Listen to the Episode Below (0:48:01)
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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)
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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 […]

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 […]