Cfo Thought Leader

In this Planning Aces episode, Jack Sweeney and co-host Brett Knowles spotlight three CFOs who are advancing their organizations' FP&A capabilities through thoughtful AI adoption. Andrea Hecht of CSAA Insurance discusses aligning generative AI with enterprise strategy and efficiency. Matthias Steinberg of MindBridge explores combining machine learning and LLMs in finance workflows. Brian Hogeland of Packer Fastener highlights how AI training and grassroots adoption can foster a tech-forward culture. Together, these leaders offer a cross-industry view of how CFOs are balancing risk, innovation, and ROI while helping their organizations navigate today’s fast-evolving planning landscape.Brett Knowles' Key TakeawaysBrett Knowles emphasizes three recurring themes: the importance of framing AI narratives carefully to avoid workforce fear, the rising expectation among employees for AI-enabled tools, and the need to align AI efforts with real business value. He also highlights the necessity of risk awareness and

When the Silicon Valley Bank crisis erupted in early 2023, Larry Roseman was already well-acquainted with market upheaval. A member of the CFO class appointed around 2020—just as the pandemic began—Roseman had weathered previous storms. He began his career amid the dot-com collapse, then advanced through the 2008 financial crisis. “Scar tissue helps,” he tells us.So when he landed in Palm Springs for a tennis tournament and learned SVB was in freefall—taking all of Thumbtack’s cash with it—his weekend plans were immediately sidelined. “Literally getting on the plane and landing, and the whole thing sort of blowing up,” Roseman recalls. “I was holed up in the hotel room for days,” working through how to ensure payroll and access to capital.That crisis became a defining moment. “That was the catalyst for us,” he tells us. Roseman used it to pivot the business away from growth-at-all-costs and toward sustainable, profitable growth. In just a few years, Thumbtack went from -$60 million in EBITDA to +$60 million.H

Back in 2003, when a recruiter lined up Kent Hoskins for a finance interview at Boosey & Hawkes, he came prepared to discuss guitar manufacturing. Instead, the executive immediately began quizzing him on music royalties—the recruiter had apparently misunderstood the brief. Hoskins didn’t get the job—at first. But two days later, he got a call: the selected candidate had quit after just 24 hours. Hoskins stepped in.That twist marked a pivotal entry into the world of music IP—one that would shape a two-decade career. At Boosey & Hawkes, he saw firsthand how legacy operations could weigh down financial performance. “Fifty percent of revenue came from physical sheet music,” he recalls, “but it only made up 15% of EBITDA.” The company licensed out the segment, cut headcount, and reinvested in IP, increasing both margins and focus. “It stayed with me… if there’s not a path to profitability from revenue, why are you doing it?”Today, as CFO of Concord, Hoskins applies the same operational lens across a $900 m

What sets John Rettig’s CFO journey apart from most is not just its length—spanning more than two decades—but its unusual symmetry. His CFO career roughly divides into two decade-long tenures: first helping scale a digital advertising firm from $15 million to $250 million in revenue, and now serving as CFO of Bill, where he’s helped lead the company from startup to public market success.When Rettig joined Bill, the company had just $13 million in revenue and a modest employee base. What drew him in, he tells us, was the combination of people, culture, and a product that placed finance operations at the center of its design. It was the first time in his career that he’d worked this closely with a finance-focused technology platform.At the time, Rettig anticipated a 10x growth opportunity—similar to his earlier experience. “It turns out, it’s 100x,” he tells us. Today, Bill has 2,500 employees, serves 500,000 customers, and supports a network of 7 million members. The company processes $300 billion in annual pa

During his decade at Google, Tim Ritters worked at the intersection of product and finance, helping to launch financial systems in collaboration with engineering, marketing, and product teams. The role gave him early exposure to cross-functional work and large-scale data environments. “Day one, you’re working cross-functionally,” Ritters tells us. He adds that this mindset became foundational to his approach going forward.When Ritters joined Gong in 2019, he says the company had already begun challenging traditional approaches to customer data. “We asked a really interesting question… what could we do if we gathered the 99% of information about your customer that was not in a traditional CRM?” Ritters explains. According to him, that original question continues to shape Gong’s mission today.Ritters tells us that Gong’s platform has since scaled to analyze more than 3.5 billion customer interactions. He says the company now serves approximately 4,700 businesses globally, including organizations such as Google,

It’s no secret CFOs frequently exit soon after a major acquisition—especially when a larger enterprise takes the reins. But Rene Ho stayed.Ho had been CFO of Taulia, a working capital fintech, when it was still an independent company. After helping lead the firm through its acquisition by SAP, he chose to stay on, guiding the company through integration while preserving what made Taulia unique.It’s a reality Ho doesn’t resist—instead, he works to make those connections scalable. That mindset reflects a broader shift under his leadership. “We’re also embedding our technology more and more into the SAP technology,” Ho tells us, noting that when he joined, the two platforms were sold separately. Now, integration enables “more of a single sale,” smoothing the go-to-market motion.While SAP Taulia continues to align its tech stack, one area remains purposefully independent: the financing operations. “We don’t use our balance sheet to finance the invoices,” Ho says. Instead, more than 30 financial institutions and n

As Cardinal Health nears its second anniversary since the company’s first investor day under CFO Aaron Alt’s leadership, steady progress has been made in its ambitious transformation. Alt reflects on the company’s trajectory since his appointment, saying, “We’ve deployed several billion dollars in acquisitions to drive our strategy.” This shift highlights the company’s focus on specialty distribution and related services—areas Alt tells us offer higher margins and greater growth potential than the company’s traditional core business.Under Alt’s leadership, Cardinal Health has pursued both organic growth and strategic acquisitions, targeting key therapy areas like gastroenterology and urology. According to Alt, the company’s balance sheet has played a critical role, enabling investments and allowing Cardinal Health to return capital to shareholders through increased dividends and share repurchases.With the recent increase in the company’s fiscal year 2026 profit estimates, Alt’s strategy appears to be paying o

In this episode of Planning Aces, co-hosts Jack Sweeney and Brett Knowles spotlight the FP&A strategies and AI adoption journeys of three CFOs—Gillian Munson (Vimeo), Dan Fletcher (Planful), and Chad Gold (FullStory). Each finance leader discusses how AI is reshaping their planning processes, from accelerating automation and revenue generation to transforming cross-functional collaboration. Brett introduces a framework for evaluating AI ROI across three dimensions: operating cost reduction, risk mitigation, and revenue generation. The episode reveals how FP&A teams are becoming catalysts for AI-driven change, extending their influence and helping to architect new organizational efficiencies and data-driven decision-making.

When Matthias Steinberg entered the CFO office at MindBridge in 2022, the audit files displayed on his laptop were already being processed by the company’s own AI. KPMG, he adds, was using the same platform to automate journal‑entry testing—work “traditionally done manual.” That shift marked “a big step toward continuous audit,” Steinberg tells us.The platform, he explains, monitors “all relevant financial flows” for two audiences. External audit firms—including “a number of the top 100 in North America”—rely on it to surface anomalies with machine‑learning speed. Enterprise finance teams deploy the same engine as a “monitoring cockpit” that flags vendor over‑charges, payroll errors, and revenue leakage so managers can intervene before profits slip. Replacing after‑the‑fact sampling with continuous insight, it gives auditors and CFOs a single source of truth. By serving both constituencies, MindBridge fuses compliance certainty with operational advantage.Capital strategy now occupies equal attention. Founded

When Andrea Hecht walks into a finance meeting, she’s not preparing for earnings calls or shareholder Q&A. Instead, her focus is inward—on aligning every financial decision with a mission that begins and ends with AAA members.CSAA Insurance, where Hecht serves as CFO, operates in 23 states and the District of Columbia. It’s not publicly traded. “We’re technically owned by our policyholders,” Hecht tells us, noting that CSAA distributes almost exclusively through AAA clubs to AAA members.That difference in ownership structure reshapes everything—from financial priorities to communication rhythms. “We don’t necessarily have those traditional…quarterly earnings calls,” she explains. “Part of the way I think about my communication is primarily inward…to make sure every decision we make is deeply tied to our strategy.”For CSAA, strategy is inseparable from service. “Our strategy is deeply tied to serving AAA members,” Hecht tells us. That’s especially vital in California, where Hecht says CSAA faces its greate

When Tom Egan walks a homeowner through the math—“If your house is worth a million dollars and you owe five hundred thousand,” he says—the traditional options surface quickly: load the balance sheet with a costly home‑equity loan or sell and hope you can find somewhere new to live. That binary choice, he explains, is exactly what Hometap set out to upend. The company’s flagship home‑equity investment lets owners “access the liquidity in their home without having to sell or take on debt,” Egan tells us.The mission “to make homeownership less stressful and more accessible” shapes his every decision. By giving capital in the form of equity, Hometap leaves monthly payments unchanged and can even “improve your credit if you use it to pay down debt.” The concept, first sketched by founder Jeff Glass, resonated immediately with consumers; Hometap has completed “18, 19 thousand of these” transactions so far, Egan tells us.Yet the CFO is careful to frame the product as a beginning, not an endpoint. He calls it “a prod

Imagine an accounts‑receivable clerk clicking through four different systems just to finish one routine task. Chad Gold sees that bottleneck instantly. Fullstory’s newly launched Workforce product maps every mouse‑stroke of such employee journeys, then surfaces friction points so companies can “make them more productive, so they can do even more value‑added things,” Gold tells us.The scene encapsulates the finance leader’s thesis: data depth wins. “The companies that have the capabilities to capture the most comprehensive sets of data in a meaningful way are going to win,” he says. That conviction drew Gold—now in his fourth CFO chapter—to the Atlanta‑based behavioral‑data platform. Fullstory records the complete digital experience of each customer, from e‑commerce clicks to SaaS workflows, and feeds the corpus into AI models that flag churn risk or recommend instant actions, such as sending a coupon to a wavering shopper. The result drives revenue and reduces churn, he tells us.For its part, Fullstory has ra

Broadcasting from Planful’s Perform 25 conference in Miami, CFO Thought Leader presents frontline finance insights in an on‑location special. CEO Grant Halloran rejects the narrative that generative AI replaces people; instead he calls it the only viable antidote to a looming three‑million‑professional accounting shortage and collapsing CPA pipeline. Halloran outlines a 30‑second, company‑wide forecasting experience that lifts productivity without swelling headcount. CFO Dan Fletcher echoes the team‑sport mantra, explaining how daily pipeline feeds, product‑usage telemetry, and strict ROI tests now steer capital allocation, meetings, and R&D growth. Attendee “on the spot” clips reinforce priorities: scaling FP&A influence, embedding AI securely, and freeing analysts from manual work so they can drive high‑cognition strategy at greater speed through data democratization, faster decision cycles, and collaborative technology roadmaps for modern finance.In this episode, CFO Thought Leader is On Location i

When a restaurant’s weekly salmon order suddenly spikes in price, Emma Whelan wants chefs adjusting menus the next morning—not tallying losses a month later. “The system will alert them if the price of salmon (has) gone up unexpectedly,” she tells us, describing MarginEdge’s real‑time cost engine. It is a small but telling vignette from Whelan’s first months as CFO, and it captures the company’s wider ambition: “MarginEdge wants to create a world where restaurant operators can focus on great food and great service without having to worry about the back office,” she tells us.Whelan explains that the platform “automate(s) the key back office tasks like invoice processing, inventory and recipe costing” by pulling data directly from point‑of‑sale systems and scanned invoices. That automation replaces hours of spreadsheet drudgery and—more critically—turns yesterday’s paperwork into today’s decision support. The salmon alert, she notes, lets owners “switch vendors, re‑price the menu, or adjust portion sizes before

When Peloton’s stock debuted in 2019, CFO Jill Woodworth believed the playbook was air‑tight. She had shifted fiscal calendars, re‑segmented reporting and shaped statements that “tell a story,” she tells us. Then COVID hit. Orders “flew nine‑fold overnight,” marketing was switched off, and customer focus narrowed to a single metric: getting bikes from order to doorstep. Wait times ballooned to “four or five months,” but earlier bets—a vertically integrated Taiwanese factory and Peloton‑owned delivery crews—proved “fortuitous,” enabling a sprint to drive delivery toward one week. When demand fell just as quickly, Woodworth slashed the bike’s price and led a restructuring that cut “$800 million of costs,” announcing it days after the board replaced the CEO. The lesson, she says, is clear: even elegant models need room for the unimaginable.That conviction now guides her first months at Prenuvo, where a patient can slip into an MRI bore and, under an hour later, leave with a radiologist‑written report on every or

For nearly ten years, Kevin Ingram knocked on S&P’s door, arguing that FM’s A‑plus rating undervalued its balance sheet. Other agencies, such as Fitch, already had the mutual insurer at AA. Each visit, Ingram presented fresh data; each time, the agency hesitated, wary of revising a long‑standing mark. Last summer, six months after FM dropped “Global” from its name, S&P finally moved, lifting the company to AA‑minus—a hard‑won validation.Throughout the campaign, Ingram stressed a core belief: “capital is our product.” By capital, he means policyholders’ surplus—the net assets that back every policy. That surplus, he tells us, doubled from $12 billion in 2014 to $26 billion today, even as insured exposure expanded far more modestly. The widening cushion lets FM keep more risk on its own books, ride out catastrophe swings, and focus on clients committed to engineering‑led resilience instead of chasing marginal premium growth.That discipline took shape after the 2017‑18 catastrophe losses, when Ingram led

When Gillian Munson pictures a Vimeo customer, she doesn’t start with a filmmaker. She imagines a Fortune 500 grocer uploading a training clip, dropping in Vimeo’s player, and hitting publish without ever surrendering control—or ad space—to a third‑party network. That simple embed workflow, she tells us, explains why “eight of the ten largest healthcare companies” and a widening roster of retailers, insurers and media giants now trust Vimeo to keep their footage private.Munson’s goal, stated plainly, is to build “the most trusted private video platform in the world.” The former Wall Street analyst has translated that ambition into a product that shuns advertising and prizes user autonomy. “We don’t sell ads,” she says, positioning Vimeo as the secure opposite of open video marketplaces. Instead, the platform thrives on a dual audience: enterprises that need friction‑free distribution and creators who still look to Staff Picks for artistic validation.That duality fuels growth. The enterprise segment reached a

This Planning Aces episode explores how finance leaders navigate volatility without drifting into political cross‑currents like tariffs. Prologis CFO Tim Arndt explains why e‑commerce triples warehouse demand and how real‑estate strategies must adapt. Genworth CFO Jerome Upton shows how disciplined leverage and balanced product exposure turn rate uncertainty into opportunity while guarding against inflationary claim spikes. Flexport CFO Stuart Leung reveals the weekly two‑hour operating cadence and scenario drills that keep freight flows nimble amid strikes, conflicts, and policy swings. Co‑host Brett Knowles connects the dots, urging planners to pair AI “agents” with dynamic rhythms that detect risk sooner and react faster.

Bea Ordonez still recalls the whirlwind of her first CFO post: a raw fintech start‑up where, in two short years, she recruited “over a hundred people,” built the processes they would follow and decided what kind of culture would bind them, she tells us. Immersing herself in every workflow taught her that finance leadership begins on the frontline—listening, questioning, then turning messy reality into structure.That builder’s reflex shapes her playbook at Payoneer today. After a decade as a global COO and a stint as Chief Innovation Officer, Ordonez now sits in the public‑company CFO chair, but she leads with the same conviction that data and customer proximity must converge. Payoneer’s mission—“talent is equally distributed globally, but opportunity isn’t,” she says—drives investments in a cross‑border payments platform serving more than two million SMBs. To scale responsibly, she has poured resources into a robust data foundation, predictive AI models that flag churn, and governance that satisfies regulator

Back in the 1990s, Dilip Upmanyu sat in a room filled with servers as he pieced together a homegrown database of costs and SKUs. His employer at the time couldn’t tell which products paid the bills; by dawn, the young financial analyst could. That improvised profitability model, he tells us, still informs his investment mindset today.Upmanyu never mistook rows of numbers for the whole story. Later joining IBM, he moved from product analytics to revenue accounting in a single year, then volunteered to face Wall Street. Preparing earnings decks, he practiced fielding questions until he could anticipate three out of four before the line opened. “Data matter only when you can explain the ‘why,’ ” Upmanyu tells us.A misstep—a brilliant job wrapped in toxic politics—taught him culture diligence. From then on he evaluated environments as rigorously as balance sheets. That instinct paid off when NetIQ sold to Attachmate: suddenly he was steering a global integration that tripled his team and required fresh capital. H