What's Rarely Measured Matters Most

finance leadership

The New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce

How consumption models, AI, and rising complexity are reshaping the CFO mandate Revenue models are becoming more complex—and for finance leaders, the consequences extend well beyond how a company bills its customers. As businesses combine subscriptions, consumption-based pricing, and other models, CFOs face new questions around predictability, visibility, cash flow, and the infrastructure needed to…
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The Economics of Removing Friction | Tami Wilson-Ciranna, CFO, Curative

Curative’s transformation from pandemic testing to employer health insurance gives Wilson-Ciranna an unusual vantage point on growth, risk and operating finance. She explains why the company committed roughly $500 million to its insurance launch and how its zero-deductible, zero-copay model is designed to remove barriers that can discourage people from seeking preventive care or taking […]

2019: Building a Health Plan Around What People Actually Do | Tami Wilson-Ciranna. CFO, Curative

When Tami Wilson-Ciranna joined Curative in April 2020, the assignment came with what now looks like a spectacularly optimistic assumption: three months. “I met with Fred on a Tuesday and I started on Thursday,” she recalls. Fred Turner, Curative’s co-founder and CEO, was leading the company’s response to COVID-19, and Wilson-Ciranna—who had retired and become…
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Why AI Shouldn’t Be Priced by the Token | Ken Stillwell, CFO, Pegasystems

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, […]

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…
Listen to the Episode Below (0:48:45)
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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 […]

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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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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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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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…
Listen to the Episode Below (0:48:23)
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