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 […]
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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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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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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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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1188: Testing Assumptions Before Burning Capital | Kevin Hettrich, CFO, QuantumScape
Kevin Hettrich walked into a conference room with a whiteboard full of numbers and a problem no one had fully articulated. QuantumScape’s leadership team was discussing how to scale an expensive R&D tool used to produce early battery materials. Hettrich had spent two weeks gathering data, talking with engineers, and analyzing manufacturing economics. Then he…
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1177: Navigating an Acquisition at the Edge of Change | Tom DiDesidero, CFO, SmartRecruiters
Tom DiDesidero describes a period when SmartRecruiters was actively taking customers from a much larger competitor. It wasn’t just momentum—it was proof. “We were stealing a lot of their customers,” DiDesidero tells us, describing how that traction became a defining signal of value. At the same time, SmartRecruiters was moving quickly on a new front.…
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Why Judgment Still Beats the Algorithm
Steve Shimizu’s finance strategic moment came during VMware’s acquisition by Broadcom, where he observed Broadcom’s disciplined, division-by-division decision making. Transitioning the EUC unit into a standalone company revealed how tightly every function interconnects—teaching him that finance leadership means orchestrating the whole system, not just managing numbers. Now Watch the Complete Episode Featuring CFO Steve Shimizu […]
1161: From Carve-Out to Standalone Enterprise | Steve Shimizu, CFO, Omnissa
An employee is on vacation in the mountains when it happens: “I left my laptop at home.” Instead of scrambling, the employee logs into a virtual desktop from another device, pulling up what looks and feels like their own PC, delivered through the cloud. That simple moment captures how Steve Shimizu describes Omnissa’s mission—helping companies…
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Scaling Payments with Strategic Precision | Kevin Wall, CFO, Stax Payments
In a meeting, Kevin Wall realized finance was too bogged down in non-strategic tasks to support commercial growth. He reorganized billing and ops functions into other departments, freeing finance to focus on pricing, commercialization, and decision support—ultimately redefining the team’s role as a true business partner driving scale and strategic impact. Now Play the complete […]
1114: Building a Smarter Funnel at Speed | Kevin Wall, CFO, Stax Payments
When Kevin Wall first stepped into industry from public accounting, it wasn’t by accident—it was through a client he already knew well. The company, in the midst of an ERP conversion and preparing to go public, saw in Wall someone who understood both their numbers and their needs. “They were familiar with me. I was…
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