CFO THOUGHT LEADER

Perry Beberman, CFO of Bread Financial and a veteran of MBNA and Bank of America, discusses rebuilding a fragile capital foundation into a platform for growth. He explores balancing retailer approval demands with credit losses, shifting funding toward consumer deposits, reading early signals in consumer credit, and using AI without sacrificing human judgment. He also shares lessons from crisis leadership, capital allocation, and finance transformation.

Guy Zeltser, CFO of Hippo Insurance and a former McKinsey consultant, charts an unconventional path from family retail to transforming a technology-driven insurer. He discusses why Hippo shrank homeowners premiums, how fees, underwriting, and investments create a more resilient model, and where AI is accelerating claims and finance. He also explores balancing quarterly results with long-term growth.

Sam Chung, Salesforce’s Chief Customer Officer, has spent more than two decades spanning finance, strategy, revenue operations, and enterprise transformation. He explores how consumption pricing changes visibility and cash flow, why CFOs are moving into product and operations, and how AI agents are reshaping finance. The conversation also examines pilots, measurable baselines, automation, controls, and accountability.

Tami Wilson-Ciranna, President and CFO of Curative, helped scale the company from pandemic testing into employer health insurance. She discusses her journey from audit and biotech to operational finance leadership. Topics include Curative’s zero-cost health plans, preventive-care economics, provider networks, AI-powered healthcare operations, market-driven strategy shifts, and expansion into new states.

Ken Stillwell, CFO and COO of Pegasystems, is a software finance leader focused on cloud transformation and enterprise growth. He discusses Pega’s journey from sub-30% cloud margins to roughly 80%, expansion-led growth, and why AI value is not about maximizing token usage. He also explores Rule of 40 discipline, measurable AI applications, executive leadership, family priorities, and staying calm through uncertainty.

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 standalone public company and sold 51% of its residential kitchen business to private equity firm 26North. What remains is a more commercially focused Middleby—and, Cerwin says, a clearer capital allocation story. The change arrives after Cerwin spent 15 years inside the company, moving from financial analyst through controllership and chief accounting responsibilities while Middleby continued acquiring businesses and building its platform. Early on, she deliberately sought work that would keep her from being siloed. That breadth now meets a narrower portfolio.Middleby’s first capital priority, Cerwin explains, is investing in core operations, followed by returning value to shareholders, with acquisitions occupying a more opportunistic third position. Meanwhile, operational excellence—lean manufacturing, SKU rationalization, product teardowns, and margin improvement—has moved squarely onto the agenda.Perhaps the bigger shift is one of visibility. Middleby wants closer connections to customers, equipment, and service networks while expanding IoT capabilities and using AI to support both customer-facing platforms and internal finance work.

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 allowed relationships to carry him across industries and into new finance roles. Boston Red Sox CFO Tim Zue recalls an unconventional path through MIT, Bain, and the Boston public schools before an email to the Red Sox opened an unexpected door at Fenway Park. Gregg Clevenger describes leaving the demands of international investment banking for Rochester, New York—a move that became both a career and personal reset. Dallas Clement reflects on arriving in Atlanta for what might have been another career stop, only to repeatedly choose to stay with Cox Enterprises as other possibilities emerged. And Michael Bannon recounts expecting his move into an operating role to happen in the Bay Area before an opportunity in London redirected both his career and his family.Together, their stories suggest that geography is more than background. Sometimes where a career unfolds helps determine what that career becomes.

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 Claude, Cursor, and ChatGPT make it increasingly easy to build applications and agents, he sees a different challenge emerging: keeping those automations reliable, observable, auditable, and cost effective once they enter production.That challenge is influencing Zapier’s product and financial agenda. Roccon points to the combination of deterministic workflows and agentic components as an important part of the company’s future. An internal review found that rebuilding certain agents with rules where possible and inference where necessary reduced costs by about 75% while improving reliability.Zapier’s financial model adds another dimension. The company has remained cash-flow positive under Roccon’s finance leadership, giving it room to make aggressive investments while maintaining discipline around ROI and net present value. His challenge to the organization is to find opportunities compelling enough to justify breaking that rule.Meanwhile, Zapier continues moving upmarket while reorganizing around AI and expanding its enterprise business. For Roccon, the finance agenda increasingly extends beyond financial results: ensuring the product delivers, sharpening the go-to-market message, and making certain that customers understand the value of what Zapier is building.

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 management—and why finance leaders may need to rethink long-held assumptions about EPM platforms, data systems and analytics.Den Boer describes a market in which capabilities once associated with EPM are increasingly emerging from multiple directions. Large language models, data platforms, business intelligence tools and EPM vendors are all extending their reach into finance. For CFOs, the challenge is becoming less about selecting a single application and more about understanding how different technologies can work together.That changing landscape is also behind Den Boer’s EPM Summit, taking place November 16–19 at the Bellagio in Las Vegas. Rather than centering on a single vendor, the event brings competing EPM providers, consultants and customers together, giving finance leaders an opportunity to compare approaches and question vendors side by side.Den Boer argues that AI will also lower the cost of experimentation. Instead of making technology choices that effectively lock finance organizations into decade-long commitments, teams may increasingly be able to test new capabilities, evaluate new data sources and quickly determine what creates value.His message to CFOs: AI is expanding the choices available to finance—but realizing its potential will require leaders who understand the entire technology landscape and know which questions to ask.

Jessica Somers, CFO of Aledade, leads finance at a physician-led value-based care company serving millions of patients. She discusses moving from dealmaking into operating leadership, investing for long-term impact, and building proprietary technology. The conversation explores AI’s role in healthcare and finance, interconnected investment bets, and why understanding the business comes before changing it.