CFO THOUGHT LEADER

The Future of Finance is Listening

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.

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Sunday · 59 min
1228: The New Economics of SolarWinds | Samuel Monti, CFO, SolarWinds
Sam Monti was working in finance at Rockwell Automation when a conversation about charging customers for technical support took an unexpected turn. A salesman suggested collecting a fee for access to the company’s engineers. Monti had another idea: Why not make it a membership, like a country club? The resulting subscription business generated $150 million in revenue in less than three years. For Monti, it was an early lesson in how rethinking a company’s operations could fundamentally change its economics. More than two decades later, that experience has particular relevance at SolarWinds, where Monti is CFO. The IT infrastructure software company has recently moved from public to private ownership under Turn River Capital while completing a transition from license-and-maintenance revenue to subscriptions. Monti views net revenue retention as the critical measure of progress. His framework combines customer retention, annual price increases, and expansion into what he calls the ARR triangle. SolarWinds, he says, is advancing on all three fronts. Meanwhile, the company is investing in agentic AI, including its Avior technology, while working to improve the operational processes that support sales, product development, and future growth. Monti’s career has included large industrial companies, private equity investments, and a difficult turnaround as CEO of Crownpeak. Those experiences have reinforced a conviction about the CFO’s role. “Wars are won by logistics, business is won by operations,” he says. At SolarWinds, that philosophy translates into two priorities: improving operational efficiency and helping the company deploy capital against a clearly defined strategy.
Wednesday · 35 min
1227: Scaling an Apparel Brand: The CFO's Capital Allocation Challenge | Neely Rosen, CFO, Greyson Clothiers
At Greyson Clothiers, opening a new store can mean committing capital long before the first meaningful returns arrive. For CFO Neely Rosen, that gap between investment and payoff has become one of the defining challenges of helping a growing apparel company scale. Greyson's business began in wholesale before expanding into e-commerce and company-owned retail stores. Its Detroit flagship, Rosen notes, has become one of its strongest performers. Now, following a capital raise in late 2024 and a NetSuite implementation, the company is preparing to introduce its own footwear line while expanding its retail presence. The question is how to fund that growth without losing sight of profitability. Rosen's perspective reflects an unconventional career. At Campbell Soup, she moved beyond auditing processes to helping build them during an SAP implementation. At Urban Outfitters, she led a major Oracle systems transformation. Later, as CFO of the Greater Philadelphia YMCA, she developed a leadership philosophy rooted in collaboration and service. Those experiences now inform her approach to technology, talent, and financial decision-making. At Greyson, Rosen works closely with merchandising, production, and supply chain leaders, particularly as tariffs and shifting trade conditions complicate operating decisions. She also sees AI changing what finance teams must deliver: not simply forecasts, but insights that anticipate what comes next. For Rosen, the challenge is deciding when to invest in stores, systems, products, and people—and when those investments should begin producing returns. As Greyson shifts its attention from infrastructure to customers and profitability, capital allocation remains the question occupying her CFO agenda.
November 1 · 59 min
1226: Anaplan's Growth Equation: AI, Profitability, and Scale | Hemant Kapadia, CFO, Anaplan
For Anaplan CFO Hemant Kapadia, one of the more revealing measures of the company’s transformation isn’t revenue growth alone. It’s the fact that Anaplan has nearly the same number of employees it had when it was taken private in 2022—even as annual recurring revenue has grown from approximately $600 million toward $1.4 billion. The company has also become materially more profitable, generating free cash flow margins in the mid-30s. That financial flexibility has helped fund a $500 million investment commitment spanning infrastructure, platform development, new applications, and artificial intelligence. Yet Kapadia’s ambitions extend beyond Anaplan’s product roadmap. Drawing on an engineering background and 14 years at General Electric, he has long viewed financial performance through an operational lens. Today, that perspective informs Anaplan’s internal AI Readiness program, an initiative he leads to identify opportunities for redesigning processes across the business. Rather than treating AI as another cost-reduction exercise, Kapadia wants employees to reconsider how work gets done—and which activities deserve their attention. “Our approach is not to say we’re gonna implement AI and we’re gonna cut, you know, thirty percent of the organization,” he explains. There’s a similar philosophy behind Anaplan’s own financial operations. By connecting sales forecasts, customer bookings, workforce costs, and cloud expenses, Kapadia says he effectively has a daily financial close, allowing investment decisions to be made during a quarter rather than after it ends. Looking ahead, his challenge is whether Anaplan can double or triple its business while keeping employee growth far below historical norms. For Kapadia, AI’s promise isn’t simply doing the same work faster. It’s changing what the organization can accomplish.
October 29 · 24 min
Evan Goldberg on the End of ERP as We Know It
At 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 More To Goldberg, the transformation rests on three developments: AI becoming the primary user interface, ERP becoming tailored to individual businesses, and software gaining the ability to perform more work autonomously. The implications extend well beyond technology. Goldberg believes finance teams will increasingly apply their analytical capabilities across the enterprise, identifying operational issues before they affect financial results. He also sees the traditional month-end close giving way to more continuous financial visibility. Rather than focusing exclusively on achieving a zero-day close, Goldberg argues that CFOs should consider how accurately their systems can reflect the business throughout the reporting period. That shift could fundamentally change how finance contributes to decision-making. “We’re really trying to free up the CFO from firefighting mode to strategic analysis mode,” Goldberg explained. For CFOs, the emerging opportunity is not simply to automate existing responsibilities. It is to redirect financial expertise toward decisions that shape business performance—while increasingly intelligent systems handle more of the underlying work.
October 28 · 29 min
1225: Nix the Clicks: Building a Finance Function That Manages by Exception | Steve Fox, CFO, Every Man Jack
When 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 IT manager connected the new ERP platform to emerging AI capabilities. Still, Fox recognizes that easier access to technology brings its own complications. With roughly 70 employees suddenly capable of creating software-driven solutions, the company established an AI oversight committee to prevent duplication and keep experimentation aligned with strategy. It’s a distinctly operational approach from a CFO whose career began in public accounting before taking him into retail management and high-growth businesses. And while Fox is enthusiastic about what technology makes possible, his guiding principle remains decidedly human: successful adoption begins with investing in people.
October 25 · 39 min
1224: Building a Cybersecurity Leader for the AI Era | Joe Iantosca, CFO, Cyera
When 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, financing that expansion involves more than allocating capital. It means understanding how customers are acquired, how products reach the market, and how new offerings become commercially successful. His operating background has also made him unusually comfortable entering customer conversations and examining the friction that can slow enterprise sales. Meanwhile, the company's investment in centralized data is helping finance pursue AI-driven automation, including potentially significant changes to the month-end close. The challenge ahead is balancing experimentation with financial discipline. Cyera encourages employees to test new ideas and move quickly, but major investments require evidence. Iantosca's priorities reflect that balance: adaptability, discipline, and the successful commercialization of new products.
October 21 · 51 min
1223: Scaling Sokin: Beyond the First $100 Million | Tom Steer, CFO, Sokin
When 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. The assumptions behind those decisions can change quickly. An anticipated shortage of engineers, for example, became less pressing as AI improved productivity, shifting attention toward sales and partnerships. Inside finance, Steer encountered a different constraint: a lean team trying to accomplish too much. Three months into the role, he and his finance director stepped away from their daily responsibilities to map the work ahead. “We can’t get this done on our own,” he recalls. Today, Steer is building systems and teams designed for substantially greater transaction volumes. His guiding question is less about what finance can accomplish today than whether its infrastructure will still work when the business doubles in size.
October 18 · 49 min
1222: Scaling Through Acquisitions, Integration, and AI | Kara Childress, CFO, Vensure Employment Solutions
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 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 structure was duplicating work. The acquisition engine was not slowing down. The finance organization needed to change before further growth made its existing structure untenable. “We need to think about this differently,” Childress recalls. The resulting reorganization reduced duplication and positioned finance to support additional acquisitions without continually adding staff. Meanwhile, a dedicated integration accounting team now brings acquired businesses into a common reporting framework beginning in their first month. Today, Vensure is also expanding its AI capabilities while Childress concentrates on client retention, organic growth, and sales investment. For a company accustomed to acquiring businesses, the next test is making its growing organization work better.
October 14 · 48 min
1221: Rebuilding Bread Financial’s Capital Foundation—And What It Made Possible | Perry Beberman, CFO, Bread Financial
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, 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 lending, the daily challenge is balancing the ambitions of retail partners with the economics of consumer credit. Retailers want more approvals. Credit executives must manage losses. Finance must determine where the returns justify the risk. “They collide all the time,” Beberman says of those competing priorities. For him, such disagreements are not organizational failures. They are essential to making better decisions. That philosophy also shapes Bread’s adoption of AI, its continuing finance transformation, and its approach to capital allocation. Technology may accelerate analysis and automate routine work, but Beberman sees little reason to surrender judgment. After nearly four decades in finance, his operating principle remains remarkably consistent: growth matters, but only when the economics support it.
October 11 · 47 min
1220: At Hippo, Growth and Risk Work Together | Guy Zeltser, CFO, Hippo Insurance
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 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’s toy business, where customer complaints and everyday transactions made the consequences of business decisions tangible. At McKinsey, another lesson emerged: even a board-approved strategy could stall when short-term financial targets overwhelmed longer-term investment. Both experiences inform his current agenda. Hippo is also deploying AI across claims and finance operations. Zeltser reports that AI now handles more than 80% of initial loss notifications, while finance has shortened its quarterly reporting timeline. With Hippo targeting a threefold or fourfold increase in profitability between 2026 and 2028, Zeltser faces a familiar tension: delivering quarterly results without sacrificing the investments required to build a larger business.
October 7 · 50 min
The New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce
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 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 Chung Key Takeaways Consumption 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. Explore the Salesforce CFO Research The conversation draws on Salesforce research examining the growing complexity of revenue models, the expanding mandate of finance leaders, and the adoption of AI and agents across the enterprise. Among the findings discussed: 65% of finance leaders report managing more than one revenue model, 71% say their companies are selling through more channels than a year ago, and 87% expect to add more consumption-based products. Explore the Salesforce CFO report at Salesforce.com/CFO-report.
October 4 · 48 min
1219: 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.
September 30 · 48 min
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.
September 27 · 41 min
1217: 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.
September 23 · 37 min
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.
September 20 · 49 min
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.
September 18 · 28 min
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.
September 16 · 49 min
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.
September 13 · 56 min
1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri
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.
September 9 · 54 min
1213: When Constructive Tension Yields Sharper Decisions | Martin Uhrik, CFO, Third Bridge
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 information “lifted the energy” inside the organization because employees had not realized their work was less profitable than they believed. For Uhrik, the experience reinforced the value of challenging the status quo. He says finance leaders should not stop when they encounter pushback; tension, opinion, and conviction are part of reaching better outcomes. It also challenged management’s assumptions about people. As Uhrik observes, leaders should not be too quick to predict how others will respond. Given the unvarnished economics, the creative teams did not retreat. According to Uhrik, they surprised the CEO—and then helped improve the business.

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