Cfo Thought Leader

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 needed to scale the operation. “It put us probably off our margin targets by a year or two,” Stillwell says. “But it was a necessary investment for us to continue to scale.” Today, he says, cloud gross margin is approximately 80%.That willingness to examine economics without losing sight of the customer runs through Stillwell’s thinking about Pega today. Growth comes largely from expanding existing customer relationships, making adoption—and the transaction volumes that follow—an important early signal. Stillwell looks for patterns across verticals, regions and customer cohorts to understand where expansion is taking h

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, f

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 expec

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

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 p

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 challenge: connecting better patient outcomes with healthcare savings and, ultimately, financial performance.That long-term orientation shapes how Somers approaches capital allocation. Aledade has built its own technology platform rather than relying on another company’s roadmap, reflecting what Somers describes as a desire to “control our destiny.” Today, that same thinking is influencing the company’s approach to AI.Rather than viewing investments as isolated projects to be stack-ranked strictly by ROI, Somers wants leaders to understand how different investments interact and compound. That became particularly import

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 accumulated across mission-critical workflows, an advantage that becomes increasingly important as AI reshapes workforce technology.That evolution is also reshaping Gordon’s finance agenda. As Harri rolls out its AI platform, understanding the changing unit economics has become a priority. AI introduces new questions around usage costs, margins, pricing, and monetization. Inside finance, meanwhile, Gordon is pursuing “automations everywhere,” with the goal of eliminating much of the routine work performed by his team and creating more capacity for insight.His operating philosophy begins further upstream. Rather than wai

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 creatives “the true state of the business.” The response was resistance: management feared that exposing weaker bottom-line results could cost the premium brand its talent and luster.Uhrik insisted. According to him, the business began showing creatives the profitability of roughly 3,000 projects a year. Teams then examined pricing, rate cards, utilization, client requirements, and whether changes requested during projects were being captured and passed along to customers.Within six to 12 months, Uhrik tells us, margins improved substantially. The feared loss of creative talent did not materialize. Instead, he says the infor

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 in charge of those things.”Until his appointment, Barzily says, he had never expected to become a CFO. He studied engineering, where he developed skills in analytics, accuracy, modeling, forecasting, and making assumptions about the future. According to Barzily, consulting then taught him to work with people ranging from individual contributors to company executives, while business development exposed him to dealmaking, legal matters, contracts, and the many participants required to bring something to life.At Tipalti, Barzily says, the chief-of-staff role initially involved running executive-team agendas, surfacing imp

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 “planted” the seed. His mentor had seen something in him that he had not yet recognized.That moment echoed the way Ma describes his development at Morgan Stanley. He credits leaders in San Francisco and New York with teaching him to take his work seriously without taking himself too seriously. According to Ma, that meant remaining curious, asking questions, and admitting when he did not know an answer.Ma says trust arrived gradually rather than through a breakthrough. Clients gave him room to learn because they saw that he would work hard, uphold values and ethics, and protect their interests. He moved from mentoring inte

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 trade you don’t make.”For Robinhood’s CFO, the line offers a double meaning—and a little fun. In the interview, however, Verma applies it to corporate resource allocation. According to Verma, it is easy to make an investment, become excited, and sell yourself on the idea. The harder work is asking the right questions and “knowing when to say no.”That standard reaches beyond securities. Verma says he applies it when Robinhood considers funding an investment, approving a marketing campaign, or pursuing an acquisition. Restraint is not timidity: Robinhood wants to grow and say yes to many opportunities, he tells us, while ba

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 sales calls. But the experience also taught him another lesson: even if a leader can do everything, “you shouldn’t do those things forever” if they pull you away from where you can provide the most value.That owner’s mindset later followed Grainger back into finance. At a healthcare software company, he tells us he was passed over for a CFO role he wanted. The executive hired instead brought a different perspective—one that showed Grainger how finance could move beyond “the debits and credits” and help shape company direction. Grainger says he ultimately became “extremely happy” they hired someone else because the experi

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 announced before year-end. That left at most 120 days. Brouilette says he was managing finance and accounting, functioning as a business-unit CFO and loading up on MBA classes at Rice because his job had seemed stable.The new assignment changed that calculation. Brouilette says he ran its finance work “soup to nuts,” covering the valuation taken into negotiations, management presentations, purchase-and-sale terms, and transition-service agreements.The transaction presented him with what Brouilette describes as a $700 million “go or no go” decision. “Yes, this was hard,” he recalls thinking, but the experience prompted th

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 operating mindset followed Schroeder to Scotts Miracle-Gro, where unfamiliar assignments became a recurring source of development. According to Schroeder, he was repeatedly placed in situations involving ambiguity, collaboration, and the need to “create something brand new that didn’t exist before.” Over time, embracing discomfort became part of his professional identity.One experience taught him what it meant to be a growth CFO. According to Schroeder, stagnant category growth had led finance into a “profit preservation” posture when leadership changes at a major retailer created an opening for Scotts to pursue a mor

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 impact, operating performance, capital allocation, risk, and long-term shareholder value, according to Fracassa. Once the decision was made, his team had just under a year to carve out a business that had been part of Timken for 85 years.That meant standing up and staffing a company, capitalizing it, unwinding entanglements, separating systems, establishing processes, and developing public-company protocols. Fracassa tells us the work reached virtually every function, including legal, HR, IT, operations, finance, treasury, and tax.His own position carried a particular tension. Although Fracassa knew where he would land aft

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 of commission for months.The immediate pressure was to reopen properties and navigate the crisis. But Ostrower says the team forced itself to “pull back” and consider how the company could emerge positioned for growth.Working with CEO David Lukes and capital markets leader Conor Fennerty, Ostrower says the team developed an answer that had not been executed repeatedly elsewhere: Separate the portfolio, create a liquid pool of assets for public-market investors, and establish a remaining company positioned for greater growth.Because the approach was untested, Ostrower says the team had no certainty about how investors

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 its spending remains prudent and directed toward investments capable of moving the business forward.The company operates in housing and healthcare, two industries Korn describes as representing about 40% of U.S. GDP combined. He tells us both depend heavily on labor while contending with regulation and legacy technology. The result is overwhelmed teams, administrative work, and consumers waiting too long or paying too much for essential services.EliseAI enters primarily through the communication layer. According to Korn, its technology handles communications and repetitive work around the clock while providing accurate

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 online while consumers, confined to their homes, purchased kitchen equipment and looked for ways to earn money. That summer brought a business boom—and immediate pressure on working capital, supply chains and forecasting.Miller says the company quickly replaced its rolling forecast with a daily forecast. One of her first CFO assignments was determining what would happen if the warehouse could not remain open as an essential business. Finance modeled scenarios “from zero to quadruple” while weighing when to continue accepting orders, when to stop, and how to manage back orders without overwhelming the business.The professi

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 challenged the belief that technology businesses could not be predictable or capitalized with debt.During the firm’s first year, Greenberg says, the team closed its first fund. She helped build operating processes, worked on the first transactions, and participated in fundraising—experiences that she says made her a better operator years later.That builder’s instinct eventually pulled Greenberg away from investing. After 18 years as a technology investor, she had come to appreciate the discipline of “separating signal from noise,” surfacing insights, and allocating capital. But Greenberg tells us that running her own

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. Their stories capture the crisis from different vantage points—from companies scrambling to protect their own liquidity to finance teams helping customers regain access to theirs.The discussion is less about the collapse of a particular bank than about how CFOs respond when ordinary financial controls suddenly prove insufficient. It explores the decisions made under pressure, the communication required to steady employees and leadership teams, and the treasury practices reconsidered afterward.The larger lesson is one CFOs understand well: resilience isn’t built during a crisis. It is built long before the crisis begins.