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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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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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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1207: Putting Guardrails Around Aggressive Growth | Jamie Schroeder, CFO, Premium Guard Inc.
Jamie Schroeder’s finance career began on the shop floor at Ford Motor Company. As part of Ford’s rotational development program, Schroeder tells us, he spent a month working in the paint shop at an assembly plant outside Cleveland. The experience was designed around “learning the business and getting your hands on the business” so that…
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1206: The CFO as an Architect of Execution | Phil Fracassa, CFO, Magna International
At Timken, it was generally known that Phil Fracassa knew he would become CFO after the company separated its steel business. But first, he tells us, the board gave him a different assignment: lead the project management office and set both resulting companies up for success. The separation followed pressure from an activist investor and…
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1205: Giving Every Decision-Maker 40 Analysts | Matt Ostrower, CFO, Link Logistics
Earlier in his career, Matt Ostrower remembers losing sleep over a decision that carried consequences for employees, lenders, and shareholders. At Site Centers, Ostrower tells us, the management team was confronting two challenges. Investor fears about the internet’s impact on retail real estate were depressing stock and bond valuations. Then Hurricane Maria struck Puerto Rico,…
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1204: When Capital Conviction Matters More Than Market Timing | Andrew Korn, CFO, EliseAI
Andrew Korn tracks growth first. EliseAI had surpassed $200 million in annual recurring revenue when he spoke with us, and Korn tells us the company had maintained year-over-year growth above 100% throughout his four and a half years there—“correlation, not causation,” he adds. That growth gives finance a clear assignment. According to Korn, EliseAI monitors…
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1202: Allocating Capital in an Age of AI | Samantha Greenberg, CFO, AlphaSense
In the early months of Francisco Partners, Samantha Greenberg sat in a room on folding chairs with the firm’s cofounders and one other colleague, planning the business. According to Greenberg, the private equity firm was pursuing an idea that many considered impossible in the late 1990s: executing leveraged buyouts of technology companies. Greenberg tells us…
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