CFO THOUGHT LEADER

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 organization can absorb them without multiply...

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 scale of the transformation, however, woul...

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 approximately 30% as Hippo reca...

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. Curative was helping respond to COVID-19, and Wilson-Ciranna—who had retired and become bored—figured she would help with the pandemic. Three months became three years. Curati...

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 backward on margin to make investments n...

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 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 allowed...

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 applicati...

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, da...

At Aledade, CFO Jessica Somers is helping finance navigate a business where investment decisions can take years to fully reveal their value. The technology-driven, physician-led company works with more than 3,000 primary care practices and touches more than 3.6 million patients, using data and technology to support proactive, preventive care. Its value-based model also creates an unusual finance c...

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 years of data ac...

When Martin Uhrik compared the margins of two visual-effects brands at Technicolor, one appeared far more profitable than the other. Uhrik tells us the reported difference prompted him to investigate. One brand showed project results only to the direct-margin level, rather than revealing fully absorbed profitability. Uhrik says he asked the business-unit CEO why the company was not showing creativ...

Shortly after Dan Barzily became CFO of Tipalti, a go-to-market transformation altered the company’s working-capital profile. One quarter later, Barzily tells us, the company missed its forecast across multiple parts of the P&L. The surprise reached back to a subject he had barely considered since his university accounting class. “It really hit me,” Barzily recalls. “I’m now the CFO, and I’m i...

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 Health’s mission and some of its people, he says the call “pla...

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 mentor there supplied a rule Verma still carries: “The best trade you ever make is often the trad...

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 Mako 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, welding, doing body work, handling customer service, and making outside sal...

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 sold and ann...

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 finance could become an informed partner to operations. That...

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 extensive board consideration of strategy, stakeholder impac...

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, leaving a portfolio of company assets out...

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 gross margins and burn while ensuring i...

In April 2020, Laura Miller stepped into her first CFO role at Pampered Chef. According to Miller, she was pregnant with her second child, working with a new CEO and joining an executive team that had never worked together in the building before the pandemic sent everyone home. Demand was anything but predictable. Miller tells us that Pampered Chef’s independent consultants could hold parties onli...

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 she was drawn to the vision because it...

What happens when a company has money—but its CFO cannot reach it? Over one extraordinary weekend, finance leaders found themselves confronting a threat few had anticipated: cash locked inside a failing bank, payroll approaching, and no certainty about what Monday would bring. This episode brings together the experiences of Ben Gammell, Larry Roseman, Dan Murphy, Stacy Tumarkin, and Sarah Spoja. T...