CFO THOUGHT LEADER

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.

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 important as Aledade weighed continued progress toward profitability against the opportunity to make larger AI investments. The result was a willingness to make bigger bets where leadership saw the potential to extend the company’s advantage.
Somers’ perspective is shaped by an earlier career in investment banking, private equity, and corporate development. Moving from advising on transactions to operating inside the businesses themselves taught her that financial results reflect countless everyday decisions—and that finance creates the most value when it deeply understands the business behind the numbers.
Her agenda now extends that philosophy to AI: not simply using technology to make finance faster, but reimagining work so the team has greater capacity for judgment, insight, and strategic partnership.

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 waiting for financial results, Gordon watches customer satisfaction, usage patterns, support activity, and customer outcomes. “Financials are outcomes of a good product and happy customers,” he explains.
That emphasis on leading indicators is accompanied by an acute awareness of downside risk. After a planned Series B financing unexpectedly collapsed in 2023, Gordon restarted the process and ultimately helped secure new funding four months later. The experience reinforced a principle he carries forward today: understand the downside and build contingency plans.
Now Gordon is stretching the CFO remit again—working as a product owner alongside Harri’s product and engineering teams. For a finance leader who has deliberately accumulated new operating experiences throughout his career, building and launching a product represents another capability still to be added.