CFO THOUGHT LEADER

CFO THOUGHT LEADER
CFO THOUGHT LEADER
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CFO THOUGHT LEADER is a podcast featuring firsthand accounts of finance leaders who are driving change within their organizations. We share the career journey of our spotlighted CFO guest: What do they struggle with? How do they persevere? What makes them successful CFOs? CFO THOUGHT LEADER is all about inspiring finance professionals to take a leadership leap. We know that by hearing about the successes — (and yes, also the failures) — of others, today’s CFOs can more confidently chart their own leadership paths across the enterprise and take inspired action.

  1. 2h ago

    The New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce

    How 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 right revenue.” — Sam ChungKey TakeawaysConsumption changes the finance equation. Usage-based revenue can strengthen the connection between what customers pay and the value they receive—but it also reduces predictability. Finance needs greater visibility into usage, billing, collections, and ultimately cash flow.The CFO is moving upstream. Today’s finance leaders cannot simply report the financial consequences of decisions made elsewhere. Increasingly, they need to participate in product, pricing, innovation, and operating conversations as those decisions are being made.AI needs an economic baseline. Rather than beginning with sweeping transformation, Chung advocates starting with use cases where companies already understand their operating metrics. Establishing a baseline makes it possible to determine whether AI is actually improving productivity, quality, and ROI.“Probably right” isn’t good enough for revenue. AI models can be probabilistic, while critical finance processes demand precision. The challenge is determining where AI can create value while maintaining the controls and deterministic outcomes that finance requires.Agents don’t transfer accountability. AI agents may increasingly perform work once handled by people, but responsibility remains with finance leadership. Controls, visibility, and oversight must evolve to encompass work performed by humans and agents alike.

    The New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce

  2. 2d ago

    2019: Building a Health Plan Around What People Actually Do | Tami Wilson-Ciranna. CFO, Curative

    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. 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, member behavior and wellness programs all come under scrutiny. Assumptions are expendable: Curative originally thought one health plan would suffice; market feedback convinced it to offer three.credentialing that Wilson-Ciranna says went from six months to 24–48 hours. Perhaps that helps explain her operating philosophy: build, measure, fix—and keep moving. For the coming year, that means supporting Curative’s capital needs, expanding its provider network, entering additional states and adding members.

    2019: Building a Health Plan Around What People Actually Do | Tami Wilson-Ciranna. CFO, Curative

  3. Sep 30

    1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems

    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 hold. 1218 Ken Stillwell AI introduces another economic puzzle. Pega chose not to build its model around maximizing token consumption. Stillwell argues that customers should use AI where it actually fits the work, selecting the appropriate model—or no AI at all—rather than treating consumption as the objective. It is an approach consistent with the Rule of 40 discipline Stillwell helped spread throughout Pega: growth matters, but so do the economics behind it. For the coming year, his priority is less about predicting every turn than preparing Pega to absorb them: staying agile, managing change and, as Stillwell puts it, remaining “calm and process focused” when the seas get rough.

    1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems

  4. Sep 27

    2017: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation

    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.

    2017: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation

  5. Sep 23

    People and Places: The Geography of a CFO Career

    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.

    People and Places: The Geography of a CFO Career

  6. Sep 20

    2016: Building the Operating System for Agentic Automation | Ryan Roccon, CFO, Zapier

    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.

    2016: Building the Operating System for Agentic Automation | Ryan Roccon, CFO, Zapier

  7. Sep 18

    When AI Changes the EPM Decision | David Den Boer, CEO, Column5 Consulting

    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.

    When AI Changes the EPM Decision | David Den Boer, CEO, Column5 Consulting

  8. Sep 16

    1215: Building Finance for the Long Game | Jessica Somers, CFO, Aledade

    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.

    1215: Building Finance for the Long Game | Jessica Somers, CFO, Aledade
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About

CFO THOUGHT LEADER is a podcast featuring firsthand accounts of finance leaders who are driving change within their organizations. We share the career journey of our spotlighted CFO guest: What do they struggle with? How do they persevere? What makes them successful CFOs? CFO THOUGHT LEADER is all about inspiring finance professionals to take a leadership leap. We know that by hearing about the successes — (and yes, also the failures) — of others, today’s CFOs can more confidently chart their own leadership paths across the enterprise and take inspired action.

Information

  • Channel
    CFO THOUGHT LEADER
  • Creator
    The Future of Finance is Listening
  • Years Active
    2014 - 2026
  • Episodes
    1.2K
  • Rating
    Clean
  • Copyright
    © Middle Market Media LLC, 2019
  • Show Website
    CFO THOUGHT LEADER

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