What's Rarely Measured Matters Most

CFO Leadership

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

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…
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2017: 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 (0:41:25)
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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 […]

2016: 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 (0:49:03)
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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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1213: When Constructive Tension Yields Sharper Decisions | Martin Uhrik, CFO, Third Bridge

When Martin Uhrik compared the margins of two visual-effects brands at Technicolor, one appeared far more profitable than the other. Uhrik tells us the reported difference prompted him to investigate. One brand showed project results only to the direct-margin level, rather than revealing fully absorbed profitability. Uhrik says he asked the business-unit CEO why the…
Listen to the Episode Below (0:54:11)
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1212: When Working Capital Rewrites the CFO Agenda | Dan Barzily, CFO, Tipalti

Shortly after Dan Barzily became CFO of Tipalti, a go-to-market transformation altered the company’s working-capital profile. One quarter later, Barzily tells us, the company missed its forecast across multiple parts of the P&L. The surprise reached back to a subject he had barely considered since his university accounting class. “It really hit me,” Barzily recalls.…
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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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1209: Finding a Larger Voice in the Room | Ross Grainger, CFO, Nasuni

Ross Grainger remembers an early chapter of his career when finance was only one part of the job. After stepping outside a traditional finance path to own and operate a Maako auto-body franchise, Grainger tells us he learned what it meant to “act like an owner.” That sometimes meant cleaning toilets, learning to paint cars,…
Listen to the Episode Below (0:33:12)
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1208: Quality, Trust, and Scale | Cal Brouilette, CFO, Flatiron Health

Cal Brouilette recalls a sleepless night in Houston, speaking at 3 a.m. with someone from Blackstone about a purchase-and-sale agreement and transition-service agreements. It concerned a power-plant portfolio sale at Direct Energy, a Centrica subsidiary, that Brouilette places in 2013. According to Brouilette, the assignment arrived in late September, when the CEO wanted the portfolio…
Listen to the Episode Below (0:46:12)
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