Synopsis
CFO THOUGHT LEADER is a ground-breaking business podcast, hosted by Jack Sweeney that brings you first hand accounts of CFOs who are driving change within their organizations.Our interviews capture their actions so that you can learn what might work for your organization. In addition to their company history we share the career journey of our spotlighted guest: What do they struggle with? How do they persevere? What makes them successful?
Episodes
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Evan Goldberg on the End of ERP as We Know It
29/10/2026 Duration: 24minAt SuiteWorld 2026, NetSuite’s founder outlines how AI is transforming business software—and what the shift means for CFOs.When Evan Goldberg, founder and executive vice president of Oracle NetSuite, declares that ERP as we know it is over, the statement carries particular weight. Goldberg helped pioneer cloud-based enterprise software in 1998, challenging the conventional wisdom about how businesses should manage their financial and operational systems.Nearly three decades later, he sees artificial intelligence driving an equally consequential transformation.Speaking with CFO Thought Leader at SuiteWorld 2026 in Las Vegas, Goldberg described a future in which ERP systems do more than organize information, automate transactions, and generate reports. Increasingly, they will anticipate problems, recommend solutions, and execute work—with human oversight.Read MoreTo Goldberg, the transformation rests on three developments: AI becoming the primary user interface, ERP becoming tailored to individual businesses, a
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1225: Nix the Clicks: Building a Finance Function That Manages by Exception | Steve Fox, CFO, Every Man Jack
28/10/2026 Duration: 29minWhen Steve Fox joined Every Man Jack in 2021, the men’s personal care brand had a new private equity owner and an ambitious growth agenda. Carlyle Group saw an opportunity: a widely distributed brand that had never invested heavily in marketing. The challenge was finding the operating leverage to fund that investment.For Fox, the answer increasingly lies in technology.At Every Man Jack, a company known for its outdoor-inspired grooming products, the finance team has remained at five employees even as transaction volume has tripled. Fox credits investments in technology and a growing emphasis on automation.The initiative even has a name: “Nix the Clicks by 26.”The goal is to eliminate manual transactions and replace traditional workflows with functional command centers where employees supervise automated processes, investigate exceptions, and monitor business performance.The transformation gathered momentum after Every Man Jack implemented NetSuite in September 2025. A month later, at SuiteWorld, the company’s
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1224: Building a Cybersecurity Leader for the AI Era | Joe Iantosca, CFO, Cyera
25/10/2026 Duration: 39minWhen Joe Iantosca arrived at Cyera as CFO, his first hire wasn't an accountant or an FP&A professional. It was a data engineer.For Iantosca, the decision reflected a conviction formed over years of working inside technology companies: Finance cannot help steer a business without reliable access to the information driving it.That conviction first took shape at Palantir, where he witnessed the impact of centralizing financial and operational data. At BetterCloud, where his responsibilities eventually expanded into the COO role, he carried the lesson further, connecting product, marketing, and business information into a common analytical foundation.At Cyera, that experience has become especially relevant.The five-year-old cybersecurity company operates across 15 countries, employs approximately 2,000 people, and has completed seven acquisitions. Its ambition is to build a comprehensive AI security platform that helps enterprises adopt artificial intelligence while protecting sensitive data.For Iantosca, fin
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1223: Scaling Sokin: Beyond the First $100 Million | Tom Steer, CFO, Sokin
21/10/2026 Duration: 51minWhen 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 to experience was the challenge of building a finance organization capable of keeping pace.Sokin helps multinational businesses manage cross-border payments, currencies, and treasury operations across fragmented banking systems. Its infrastructure supports payments to 170 countries, while a growing embedded-finance offering allows other companies to bring Sokin’s capabilities to their own customers.For Steer, the challenge is deciding where to place the next investment. North America has emerged as Sokin’s fastest-growing market, while embedded payments and AI-enabled treasury tools present additional opportunities. Each requires capital, talent, and organizational attention.Th
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1222: Scaling Through Acquisitions, Integration, and AI | Kara Childress, CFO, Vensure Employment Solutions
18/10/2026 Duration: 49minAt 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 multiplying its own inefficiencies.That challenge has become familiar territory for Childress, whose career took an unusual turn when she left public accounting to join Vensure as COO. Having previously served as the company’s outside auditor, she knew its finances. Operations offered something different: an opportunity to remove roadblocks and help people perform better.As Vensure expanded into global payroll, HR technology, and human capital management services, Childress’s responsibilities broadened to include finance and the presidency. Along the way, she confronted a finance organization whose regional and divisional st
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1221: Rebuilding Bread Financial’s Capital Foundation—And What It Made Possible | Perry Beberman, CFO, Bread Financial
14/10/2026 Duration: 48minWhen 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, would demand patience.Today, Beberman points to a substantially different financial foundation. Bread has paid down more than 70% of its parent-company debt, built capital beyond established targets, and shifted direct-to-consumer deposits from less than 5% of funding in 2020 to more than half.The changes have given Bread greater capacity to invest in technology, support growth, and return capital to shareholders.Still, Beberman is quick to explain that financial discipline is not simply about strengthening a balance sheet. At Bread, whose products include co-branded credit cards, private-label cards, and installment len
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1220: At Hippo, Growth and Risk Work Together | Guy Zeltser, CFO, Hippo Insurance
11/10/2026 Duration: 47minIn 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 recalibrated the risks it was willing to carry. For Zeltser, the decision marked a turning point in a broader transformation—one that would move the company toward profitability and a more diversified business model.Today, Hippo supports more than 60 insurance programs, generating fees and commissions alongside underwriting and investment income. That mix matters. Fee revenue offers greater predictability, while improved underwriting performance gives the company confidence to retain additional insurance risk.Zeltser’s approach reflects an unusual career path. Before McKinsey and corporate finance, he worked in his family
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The New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce
07/10/2026 Duration: 50minHow consumption models, AI, and rising complexity are reshaping the CFO mandateRevenue 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 to manage revenue from beginning to end.Salesforce Chief Customer Officer Sam Chung brings an unusually broad perspective to these challenges. Over more than two decades at Salesforce, his roles have spanned revenue operations, finance and strategy, CFO of Salesforce.org, enterprise transformation, and customer leadership. In this conversation, Chung explores why CFOs must move further into operations, product, and technology; how AI and agents are changing the economics of finance; and why greater automation does not diminish the need for financial controls, precision, and human accountability.“You can’t have probably
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2019: Building a Health Plan Around What People Actually Do | Tami Wilson-Ciranna. CFO, Curative
04/10/2026 Duration: 48minWhen 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. Curative ultimately administered 36 million COVID tests.Then came the harder question: What was phase two?Curative wanted to remain in health care, but its leaders concluded that influencing care meant becoming the payer. The result was an employer health plan built around zero deductibles and zero copays, with members encouraged to complete an early baseline visit and engage in preventive care. Curative rolled roughly $500 million into starting the insurance business.For Wilson-Ciranna, now president and CFO, the experiment is increasingly about what the data says. Medical loss ratios, provider costs, network economics, me
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1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems
30/09/2026 Duration: 48minWhen 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
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2017: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation
27/09/2026 Duration: 41minFor 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
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People and Places: The Geography of a CFO Career
23/09/2026 Duration: 37minCFO 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
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2016: Building the Operating System for Agentic Automation | Ryan Roccon, CFO, Zapier
20/09/2026 Duration: 49minAt 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
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When AI Changes the EPM Decision | David Den Boer, CEO, Column5 Consulting
18/09/2026 Duration: 28minAI 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
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1215: Building Finance for the Long Game | Jessica Somers, CFO, Aledade
16/09/2026 Duration: 49minAt 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
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1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri
13/09/2026 Duration: 56minFor 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
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1213: When Constructive Tension Yields Sharper Decisions | Martin Uhrik, CFO, Third Bridge
09/09/2026 Duration: 54minWhen 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
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1212: When Working Capital Rewrites the CFO Agenda | Dan Barzily, CFO, Tipalti
06/09/2026 Duration: 36minShortly 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
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1211: Mission, Means, and the Will to Grow | Jonathan Ma, CFO, Sutter Health
02/09/2026 Duration: 39minJonathan 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
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1210: The Best Trade May Be the One You Don’t Make | Shiv Verma, CFO, Robinhood
30/08/2026 Duration: 53minSix 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