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 […]
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…
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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…
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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…
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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…
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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…
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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,…
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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…
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