What's Rarely Measured Matters Most

capital allocation

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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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…
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Inside the Economics of Consumer Lending | Perry Beberman, CFO, Bread Financial

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, […]

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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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 […]

1217: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation

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…
Listen to the Episode Below (0:41:38)
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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 […]

1216: Building the Operating System for Agentic Automation | Ryan Roccon, CFO, Zapier

At Zapier, the rise of AI is changing more than the automation products customers build. It is reshaping how the company organizes, invests, prices its offerings, and thinks about its next stage of growth. COO and CFO Ryan Roccon describes Zapier’s emerging role as the place where AI-built work actually runs. As tools such as…
Listen to the Episode Below (0:49:16)
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1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri

For Jack Gordon, the CFO role at Harri increasingly extends beyond finance—and into the mechanics of how an AI-powered business scales. Harri, a workforce operating system focused on hospitality, has evolved from a point solution into a broader platform spanning talent acquisition, workforce management, and employee engagement. Gordon says the company’s opportunity rests partly on…
Listen to the Episode Below (0:56:46)
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1211: Mission, Means, and the Will to Grow | Jonathan Ma, CFO, Sutter Health

Jonathan Ma recalls being at his parents’ home in Nebraska one Saturday when his Morgan Stanley boss called with advice: pursue an opportunity at Sutter Health. After nearly 15 years, the mentor believed the retiring treasurer’s position could be Ma’s next step. Ma tells us he had not considered the opportunity. Although he knew Sutter…
Listen to the Episode Below (0:39:28)
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1210: The Best Trade May Be the One You Don’t Make | Shiv Verma, CFO, Robinhood

Six weeks before Lehman Brothers went under, Shiv Verma tells us, he joined a hedge fund as the world felt like it was falling apart. After building structured-credit and CLO models at J.P. Morgan from 2006 to 2008, Verma says he helped buy back assets originated at par for five cents on the dollar. A…
Listen to the Episode Below (0:53:27)
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