CFO THOUGHT LEADER

When Tom Steer joined Sokin as CFO, he already knew the international payments company unusually well. As an investment banker at FT Partners, he had advised Sokin through a capital raise during a difficult period for fintech funding. He knew its leadership, its financial projections, and the ambitions behind its growth. What he had yet […] The post 1223: Scaling Sokin: Beyond the First $100...

At Vensure Employer Solutions, completing an acquisition is only the beginning. The company has acquired roughly 120 businesses in eight years, and each new addition enters an integration process containing some 1,400 steps. For CFO and President Kara Childress, the challenge is not simply bringing more companies into the fold. It is making certain the […] The post 1222: Scaling Through Acqu...

When Perry Beberman arrived at what is now Bread Financial, the company had a balance sheet problem. It was carrying too much leverage, had insufficient capital, and needed a more disciplined approach to funding its lending business. For a finance executive who had spent decades navigating consumer credit cycles, the assignment was familiar territory. The […] The post 1221: Rebuilding Bread...

In 2023, Hippo faced what CFO Guy Zeltser describes as perhaps the worst quarter in the insurance company’s history. The response was not to chase growth harder. Instead, leadership made a decision that would have seemed counterintuitive during the company’s earlier expansion: shrink part of the business. Between 2023 and 2024, homeowners insurance premiums declined […] The post...

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 t...

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 […] The post 2019: Building a H...

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 […] The post 1218: Why Pegasystems...

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 […] The post 2017: A...

CFO careers are often described through titles, companies, and accomplishments. But another force can quietly shape the journey: place. In this themed episode of CFO Thought Leader, five finance leaders reveal how geography influenced the opportunities they encountered, the relationships they built, and the choices they made. Mike Brower explains how Wyoming’s close-knit business community [&#8230...

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 […] The post 2016: Building the Operating System for Agentic Autom...

AI is rapidly changing not only what finance technology can do, but how CFOs should think about the technology stack itself. In this bonus episode of CFO Thought Leader, David Den Boer, CEO of Column Five and Darwin Analytics, joins Jack Sweeney to explore how AI is reshaping enterprise performance ...

Sinohe Terrero still remembers the timing. He joined Envoy in January, only to see the workplace transformed just two months later as offices around the world shut down because of COVID. The company had been building products for offices, but suddenly, almost no one was going to the office, Terrero tells us. That abrupt shift […] The post 1197: The CFO Who Learned Finance by Owning Sales | S...

When Martino Cadoni joined DeepL, he arrived with an unusual perspective—he already knew the company’s product firsthand. Earlier in his career at Klarna, he had helped introduce DeepL as a translation solution, making the transition from customer to CFO especially meaningful. Today, DeepL is backed by investors including HV Capital, Benchmark, Index Ventures, ICONIQ, and […] The post...

When Jean Compeau joined Sonar as CFO in March 2025, AI coding was not yet dominating industry conversations. By the summer and fall that followed, however, the landscape had shifted dramatically. Today, AI agents are producing software code at a pace that humans cannot easily verify, creating both opportunity and risk. That shift sits at […] The post 1195: When Finance is at the Center of t...

Each day, Stacey Jenkins watches a different set of indicators than the quarterly financial results that eventually appear on a report. Candidate applications, recruiter activity, and other throughput measures help tell the story of where Aerotek’s business may be headed. Financial results are “the lagging indicator,” Jenkins tells us. That perspective reflects how she views [&#8...

When Jesse Waldron describes Thyme Care’s work, he begins with the patient experience. Cancer patients, he explains, are often thrust into a healthcare system that can feel overwhelming both financially and emotionally. That reality sits at the center of Thyme Care’s mission. As an oncology care navigation company, Thyme Care helps patients move through their […] The post 1193: B...

Five weeks into her role as CFO of Catalant, Christina Spade is helping guide a company that she believes is positioned for a different era of consulting. Catalant was founded out of Harvard Business School in 2013 and began as an independent consultant matchmaking company, Spade tells us. Today, she describes the firm as a […] The post 1192: Building Through Disruption | Christina Spade, CF...

When David Forlizzi describes Salsify, he begins with a simple observation: “We all use it every day.” Unlike some of the highly technical software businesses where he previously spent his career, Salsify’s value proposition is visible to anyone who shops online. Product content sits at the center of the company’s platform, Forlizzi tells us. Whether […] The post 1191: From Compl...

When Jaylene Kunze was asked to help rebuild a struggling subsidiary in the United Kingdom, she packed up her family and moved overseas with her nine-month-old daughter. The assignment was one more example of the type of challenge that would come to define her career. Rather than following a traditional finance path, Kunze gravitated toward […] The post 1190: Fixing What Growth Tries to Hide...

A conversation from years earlier still stands out to Bruno Annicq. While working at AOL, he was supporting business leaders and helping tell the story of the business through data and analytics. Then a senior executive, Holly Hess, approached him with an unexpected suggestion: Why not become the CFO of AOL’s platforms business? Annicq’s reaction […] The post 1189: Why Finance Should Lead wi...

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 […] The post 1188: Testing As...