CFO Thought Leader

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.His ability to adapt comes from a varied career path—public accounting at Ernst & Young, investment banking at Bear Stearns and JPMorgan, and operational finance at eBay, where he helped spin off PayPal. At Thumbtack, a national home services marketplace, he's scaled the finance team tenfold and implemented a discipline around contribution margin, hire rate, and CAC.“The P&L doesn't lie,” Roseman tells us—especially in times of crisis, when it's clarity, not comfort, that defines the leader.

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 million IP portfolio. After joining Concord through acquisition in 2017, he became CFO in 2021. Strategic forecasting now combines AI and streaming data—insights that recently helped identify renewed demand for the Creed catalog. “We could see it from the consumption,” he tells us, which triggered targeted marketing and revenue lift.

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 payment volume and has grown to $1.5 billion in revenue.Much of that growth, Rettig explains, has come from addressing the operational challenges of small and midsize businesses. Early efforts to modernize paper-based processes helped shape the company's current offerings, which span accounts payable, receivable, corporate cards, and cash flow management.“We become the center of their financial operations,” Rettig says of the platform's role. His focus remains on scaling Bill's impact across the “Fortune 5 million.”

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, LinkedIn, Canva, and Anthropic. The platform, Ritters notes, helps customers extract insights from a broader set of data sources—including conversations, emails, and documents—that may not be captured in traditional CRM systems.Ritters believes that AI adoption has made Gong's value proposition more tangible to prospective buyers. “When [they] peel back the onion… they start seeing some of the incredible sort of results,” he says. According to Ritters, some customers have reported “halving of deal cycle times” using the platform.All of Gong's growth to date has been organic, Ritters tells us, and he views the company's trajectory as part of a broader evolution in how organizations approach customer intelligence. “The sweet spot we're in right now,” he says, “is helping companies make smart business decisions.”

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 non-bank entities fund those transactions.

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 off. “We're doing what we said we were going to do,” Alt emphasizes, underscoring the transparency and accountability he has fostered during his tenure. Looking ahead, the company's growth trajectory is set to continue as it leverages acquisitions and internal investments to expand its portfolio and drive long-term value creation.

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 in Ottawa, MindBridge had completed several Canadian and U.S. venture rounds; its last raise before Steinberg arrived was led by Silicon Valley's PeakSpan, he tells us. Charged with “professionalizing the business and also [doing] a fund‑raise,” he orchestrated a recap that introduced Boston‑based PSG Equity and offered early backers a partial exit. The diversified balance sheet, Steinberg says, funds the product roadmap that keeps KPMG—and every controller chasing real‑time insight—a step ahead of the next anomaly. Fresh capital also fuels deeper AI R&D and global reach, he adds.

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 greatest insurance concentration and the most market volatility.While other insurers have exited the state, CSAA has stayed the course. “It's been really gratifying to see what we can do,” Hecht says. Balancing capital protection and member coverage remains a daily challenge—one she's eager to embrace.With AM Best as CSAA's key external stakeholder, Hecht's metrics of success differ from peers in public or PE-backed companies. “It's a really interesting balancing act,” she tells us—and one that redefines what it means to lead finance from the inside out.

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 product, not the product,” an opening move toward a platform of offerings that address the full arc of ownership. Growth, he notes, is already visible as other operators enter the market—a sign of “enormous upside.”Egan's narrative reveals a strategist who sees finance as empowerment. By replacing debt with shared success, he aligns the homeowner's peace of mind with Hometap's own performance, turning equity itself into the most flexible currency a family possesses—and signaling a new era for consumer housing finance.

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 raised capital rounds through Series D and counts Kleiner Perkins, Stripes, Premier, Salesforce Ventures, GV and Dell Technologies among its backers, he tells us. Independent directors Ryan Barreto of Sprout Social and former Atlassian CFO Alex Estevez deepen the bench. After 22 years in finance, Gold values “lines, not dots”—long‑term relationships that provide partnership, not just cash. By pairing that philosophy with a platform built to illuminate every click, he aims to turn invisible friction—whether customer or employee—into the next chapter of growth. Stakeholders across the business will feel the lift, Gold predicts.

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 in Miami, where host Jack Sweeney gathers candid insights from Planful's leadership and FP&A practitioners. CEO Grant Halloran outlines why AI must boost productivity—not cut jobs—amid a historic finance talent crunch. CFO Dan Fletcher shares how product‑usage data and daily reforecasting sharpen capital decisions. Attendees add rapid‑fire priorities, from scaling forecasts to embedding secure AI.

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 it starts to impact their margins,” a response time that can separate profitable months from painful ones.Her strategic priorities echo the same urgency. Backed by Osage, Schooner Capital and Ten Coves Capital, Whelan directs new funding primarily to R&D so the software stays “at the cutting edge” of restaurant needs. Investing in talent runs a close second; Glassdoor awards and sky‑high satisfaction scores, she tells us, prove that an engaged workforce builds better products—and happier customers feel the difference. In Whelan's finance playbook, speed, clarity and culture work together, just like ingredients in a well‑seasoned dish.

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 organ and joint, Woodworth tells us. She is “learning the business” alongside technology, AI and clinical teams, convinced the company holds “so many different ways to grow,” including a new biomarker offering. Finance remains small yet “mighty,” but she will embed analysts so thoroughly that the head of clinical practice “doesn't want to be in a meeting without” them. Acting as co‑pilot to the CEO, she intends to safeguard a balance sheet that grants “every available option” for raising capital—ensuring, this time, finance anticipates both the surge and the calm that follow ahead.

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 a rigorous re‑underwriting that bolstered profitability and reserves. Drawing on decades of loss data and hundreds of engineer‑captured risk points, his team now deploys AI models to rank mitigation projects for FM's 1,600 core policyholders. Those accounts generate over $8 billion of the company's $11.2 billion (gross operating) revenue.

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 “$100 million run rate” within just a few years, Munson tells us, and she is convinced “there's a lot more to come.”

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 regulators across 190 countries.Volatility, meanwhile, no longer startles her. Having weathered the dot‑com bust, 2008, COVID, the 2023 U.S. banking shock—and now a new wave of tariffs whose ultimate impact remains uncertain—she treats upheaval as a catalyst for opportunity.For aspiring finance leaders, her path offers a signal: there is no prescribed ladder. Curiosity, operational empathy and a willingness to “lean into areas where there's no obvious right answer” open the widest doors—and keep a company's growth story moving long after the numbers are scored, through volatile cycles across global markets today.

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. He treated the chaos as a practicum in fundraising and leadership, logging the final credit hours for his CFO ambition.By the time Cloudera called in 2023, Upmanyu had stitched together every major finance discipline. Today he pushes growth by leading with the firm's public‑cloud platform and embedding AI into forecasting.

A little more than decade ago, Travis Page was hauling gear off a tour bus, criss-crossing the country with indie bands. One late night, sweat-soaked and exhausted, he noticed fans waiting in the rain simply to glimpse their favourite artist. Passion like that ought to power a business, he thought. That backstage epiphany still guides him as CFO of Crunchyroll, the world's largest anime platform.After the music industry's 2007 crash, Page hit reset—trading road cases for a Wharton MBA and, soon after, a seat at Barclays Capital. Covering entertainment firms during the Lehman-to-Barclays transition gave him, he laughs, “a five-year education in two.” The intensity paid seemed to pay off: at 30, he was head of finance at Remark Media, then a corporate-development deal maker at Demand Media.Sony Pictures Entertainment came calling next. Page helped stitch together seven anime acquisitions, culminating in Funimation's purchase and, later, the Crunchyroll merger. When Sony needed a strategic CFO to scale the nascent service, his boss put his name forward—before even asking him. He accepted on the spot.Today, Crunchyroll counts “over 15 million subscribers in 200 countries,” Page tells us, triple the total since the 2021 merger. His playbook pairs disciplined capital allocation with fan-first intuition: license or co-produce 99 percent of content in Japan, then “explode” each franchise across streaming, film, and consumer products. Finance's role? Embedded FP&A analysts sit in strategy off-sites, ensuring every creative gamble lands on a sound financial stage—just like those fans waiting in the rain taught him years ago.

It was Friday the 13th in March of 2020, and Steven Miller was staring at a suddenly irrelevant budget. Hours earlier Warby Parker had shuttered every one of its 280 stores to protect employees and customers. “Remember that plan we just approved?” he asked the leadership team. “Forget it.” In its place he introduced PAR—Pause, Adjust, Redeploy—a framework that let finance review cash daily, pivot marketing dollars to booming e-commerce, and preserve innovation spend while the world locked down. The episode crystallized Miller's philosophy: data guides decisions, but agility preserves advantage.Raised as a strategy consultant at Monitor Company, Miller learned early to hunt for competitive leverage. A New York City Urban Fellows stint deepened that lesson when a commissioner advised him to “read the budget if you want to know a society's values.” The line sent him chasing the intersection of money and mission—from Flatiron's venture trenches to Majestic Research, where the 2008 crisis forced layoffs and, ultimately, a sale to ITG that began with his cold call. Warby Parker appealed because it made a tangible product and pledged social impact.Miller joined when the firm had 20 employees and no stores; today it approaches 4,000 people and, he tells us, opens “40-plus new locations a year.” Eight capital raises and a 2021 direct listing later, his remit is constant: align capital with purpose. By measuring four-wall EBITDA, inventory turns, and cost lines against revenue, Miller ensures every dollar advances a simple mission—help more people see clearly around the world daily.

It was a morning commute Chris Greiner had made hundreds of times before. Living in old Shanghai and working in the city's sleek business district, Greiner's daily drive to the Jin Mao Tower often stretched well beyond an hour. But on this particular day, his driver told him they'd arrive in just 30 minutes. Puzzled but intrigued, Greiner went along—only to discover the traffic patterns had shifted. “They repainted the lines,” the driver told him with a grin. The same bridge, same road—just used differently.Greiner never forgot the lesson. As CFO of Zeta Global, he often draws from that experience when approaching business challenges. “You might be fixed in your infrastructure, but there's almost always another way through,” he tells us.That mindset is now shaping Zeta's evolving AI strategy. Rather than applying AI for efficiency's sake, Greiner tells us his team follows the real patterns of work—starting with customer behaviors. “We began by observing how marketers use our platform,” he says, “then built automations to eliminate keystrokes and surface next-best actions.”Now, the finance function is adopting the same approach. Greiner's team is analyzing daily tasks across accounting, FP&A, and sales operations to identify which can be codified and automated. Zeta is building agent-based workflows that transform data into actionable insights—at the push of a button.“We're letting the work show us where to go,” Greiner says. And like that rush-hour bridge in Shanghai, sometimes a better route is just a few new lines away.

Jerome Upton still remembers the silence that descends just before a game begins. As captain of his college team, he'd scan the huddle, gauge nerves, and ask, “What does winning look like today?” “That's where I learned the power of shared goals,” Upton tells us. Years later, the Genworth Financial CFO opens staff meetings similarly—then hands teammates room to execute.The first bold play of his career came soon after graduation. At a small insurer, Upton stunned mentors by jumping to KPMG. “I needed wider fields,” he explains. Eight years of audits sharpened his technical vision, yet the move that truly stretched him arrived when GE Capital—Genworth's predecessor—offered a divisional‑controller seat with global scope. Overnight his “team” expanded ten‑fold, teaching him to win through trust rather than touch‑every‑file oversight.International assignments followed: boardrooms in Europe, investor roadshows in Asia, client visits in Latin America. Hearing customers critique products in real time “made finance feel less like a ledger and more like a heartbeat,” he says. That perspective proved vital during Genworth's post‑crisis crossroads. Tasked with raising capital quickly, Upton orchestrated a minority IPO of a foreign subsidiary, executed at speed and premium valuation. The deal slashed leverage and revealed hidden asset value.Today his playbook balances share buybacks and debt reduction with growth bets such as CareScout. Multi‑year downside modeling safeguards the core, while his Gretzkyesque mantra—skate where the puck is going—keeps him focused on tomorrow's opportunity.

t was sixty days into his new role when Brian McClintock tells us he realized the company's monthly “profit” was actually a million-dollar loss. As the CFO reviewed the financials, he discovered that each rosy figure concealed a troubling truth. For many executives, panic might have followed. Instead, McClintock's response underscored a key principle: remain calm and stay focused on data-driven solutions.As he dug deeper, a misalignment of actual costs and revenue assumptions emerged, revealing the precarious financial situation that demanded immediate action. Determined to right the ship, he mapped a bold course, recommending a strategic acquisition that would fortify cash flow and support operational improvements. “We had to leverage operational insights along with our existing relationships,” McClintock explains, adding that his experience in complex telecom environments allowed him to see beyond the numbers. The result was rapid transformation. Within a year, the company went from losing seven figures each month to generating a million dollars in monthly EBITDA—proof of the CFO's insistence on purposeful change.

It was a first meeting Naeem Ishaq tells us he'll never forget: stepping into the Chief Product Officer's office at Salesforce, he began pitching a bold new pricing model. Yet the officer cut him off, bluntly telling him to “figure out the (numbers) first, then we can talk strategy.” Ishaq admits he had inherited something of a mess when it came to the data. Despite the tough feedback, however, he refused to give up. He dove deeper—verifying metrics, updating budgets, and clarifying every detail—determined to show he could be both a financial expert and a strategic partner. By persevering rather than shrinking from the challenge, he eventually earned the trust needed to advance his pricing insights.That wake-up call echoed lessons he'd learned as a child of immigrants. Ishaq tells us his father arrived in the United States with just twenty dollars, fueled by grit and hope. Growing up, Naeem watched firsthand how determination could unlock opportunity—even if the odds seemed stacked. This conviction led him to form his first business in 1999, forging a passion for technology-driven solutions that would guide him in future roles at Salesforce, Square, and eventually Checkr.Today, as CFO and Chief Strategy Officer at Checkr, Ishaq's mindset blends rigorous analysis with an entrepreneurial spark. He believes finance leaders create the most impact when they go beyond reporting numbers to envision what's possible—and then rally others around that vision.

It was the kind of boardroom moment that separates finance professionals from finance leaders. Tony Jarjoura, now CFO of Gigamon, found himself surrounded by audit committee members as a dense, highly technical tax strategy unraveled before them. Despite having pored over legal memos and internal reviews, the room still looked puzzled—until Tony spoke. In just two sentences, he distilled thousands of hours of technical effort into a clear, accessible takeaway. “That was the moment,” he tells us, “when I realized the power of translating complexity into clarity.”Tony's journey to that moment began with a professor's advice back in university: go Big Four, earn your CPA, and the world will open up. He took it to heart, spending 15 years at Ernst & Young in San Francisco, embedded in Silicon Valley's IPO engine room. At EY, he wasn't just crunching numbers—he was watching ideas travel from whiteboard sketches to billion-dollar listings. Companies like Atlassian, Okta, and Workday became case studies in how finance underpins innovation.When he stepped into industry during the COVID years, Jarjoura traded IPO war rooms for the operational depths of Gigamon. He jokes about never having recorded a journal entry before—but quickly embraced the inner mechanics of finance operations. Today, he views FP&A not as a rearview mirror but as a GPS system for business decision-making. “Finance has to be the connective tissue,” he says, “translating data into decisions that shape where we go next.

“It wouldn't surprise me. No, it would be exciting.”That was Adam Ante's initial response when asked if five years from now, he could imagine himself still in the C-suite—but not as a CFO. The comment seemed to linger in the air, hinting at a deeper current in his career journey. Ante, who had led Paycor through an IPO, a pandemic, and most recently, a $4.1 billion sale to Paychex, wasn't just closing out a CFO chapter—he may have been opening something entirely new.While he later softened the sentiment, suggesting he might be surprised if he moved beyond finance, his earlier candor revealed a finance leader attuned to operations—and perhaps transformation.Years earlier, Ante had flown weekly to Colorado, struggling to integrate a newly acquired company. “I felt like I was failing,” he tells us. The lesson was hard-won: strategy and spreadsheets are meaningless unless you can move people with them. That shift—from financial executor to business operator—has defined his trajectory ever since.His strategic mindset matured further with Extreme Ownership, a book he credits with changing how he approached leadership, cross-functional collaboration, and results.Now, as the dust settles on Paycor's acquisition, Ante's priorities have shifted once again—to preserving what works, aligning teams, and honoring the customer experience.

Host Erik Zhou sits down with Amber Papp, VP of Finance at Scentbird to explore the unique challenges of accounting in the e-commerce space. From managing a massive inventory of over 700 fragrances to navigating rapid growth and making smart automation decisions, Amber shares firsthand insights on what it takes to keep financial operations running smoothly at a high-growth, subscription-based company.Amber and Erik also dig into relevant themes like the role of AI in accounting, balancing efficiency with cost when evaluating new financial tools and systems, and the never-ending pursuit of data integrity.And as the episode closes, Amber shares a truly unexpected budget request—one that involved a Cybertruck, a demolition derby, and a marketing team with big dreams.

Fresh out of a hedge fund analyst role, Erik Rothschild walked into an interview at a Chicago-based trading firm and did something unexpected—he pitched actual trade ideas to the portfolio manager across the table. That bold move earned him a spot on the team, and eventually, a portfolio of his own. “That whole experience taught me how to assess decisions through the lens of an investment,” Rothschild tells us. It's a mindset that has quietly shaped every leadership decision he's made since.Rothschild's early career was forged in the high-stakes world of investment finance during the 2008 financial crisis. He later transitioned into corporate finance, helping build out the FP&A function at Sovereign. When the CFO unexpectedly departed, Rothschild found himself reporting directly to the CEO—presenting financial results to the board and leading a complex equity raise. “It was both exciting and stressful,” he recalls, “but I knew I had a window to gain experience that would last a lifetime.”What sets Rothschild apart is the investor's mindset he brings to the CFO role at Cin7. He encourages his team to think in bets—evaluating risks, testing hypotheses, and acting decisively. He's also a champion of simplicity and automation, challenging his team to reduce low-ROI cycles and focus on what matters most.

It was a late-night meeting room lit by the glow of Excel spreadsheets and half-empty coffee cups. Brian Carolan, then a rising finance leader, looked around the table and saw not just fellow accountants and analysts but a collection of people relying on him to bridge data and strategy. In that moment, he felt the weight of a CFO's responsibility keenly. “Finance is never only about numbers,” Carolan tells us. “It's about connecting the dots for everyone in the room.”Years earlier, he had traded the security of a Big Four firm for a nascent startup, learning quickly that growth rarely follows a neat script. One day, he might be projecting cash flow; the next, mending fractured vendor relationships. Each challenge Caloran tells us strengthened his conviction that adaptability drives sustainable success. He carried that lesson into a complex M&A deal, where he orchestrated integration across multiple departments. “M&A isn't just consolidation,” Carolan tells us. “It's a chance to redefine the culture, if you're willing to listen.”As his influence grew, Carolan found that effective CFOs serve as translators—turning raw data into forward-looking stories. After a particularly tense board presentation, he recalls a mentor pulling him aside. “Numbers matter, but so does the narrative behind them,” the mentor said. That advice remained Carolan's compass. In every leadership role since, he has championed an inclusive approach, ensuring finance is a unifying force that galvanizes operations, sales, and strategy under one clear vision. And that, Carolan tells us, is how real transformation takes root.

In this episode of Planning Aces, three forward-looking finance leaders share how they're transforming planning and forecasting inside their organizations. CFO Kevin Rhodes of Extreme Networks discusses the dual lens through which he evaluates AI—external monetization and internal productivity. Brendon Sullivan, CFO of 2X, reveals how a post-PE investment reality check led him to pioneer a weekly reporting cadence to drive faster decision-making. Meanwhile, Gabi Gantus of Mytra AI draws on her Tesla FP&A roots to illustrate how finance can lead long-term operational planning. Brett Knowles joins Jack Sweeney to unpack key insights and the broader implications for FP&A.Co Host Brett Knowles emphasizes the need to distinguish internal and external AI use cases, applauds CFOs who are expanding AI's role beyond headcount reduction, and highlights how AI can sharpen decision-making and compress process cycles. He underscores the CFO's evolving role in overseeing cross-functional strategy, particularly as AI accelerates organizational complexity. From sales effectiveness to real-time alerting, Knowles sees AI as a vital lever in both financial performance and agility, cautioning laggards that competitors are already moving ahead.

It was a pivotal moment Brian Robbins tells us he'll never forget: stepping onto a makeshift stage to address some 400 employees just minutes before a key 8-K filing would publicly announce the potential sale of a major business unit. The room bristled with anxiety—people worried about their jobs and the future of the company. Robbins recalls that, instead of relying on scripted talking points, he spoke from the heart and vowed to keep everyone informed as events unfolded. By offering that openness, he reinforced his belief that finance isn't just about numbers, but about building trust and forging a clear path forward.Today, that spirit of transparent communication fuels Robbins's approach as CFO. Above all, he prioritizes strong relationships across every organizational function, from sales and marketing to product and engineering. This is why go-to-market execution, he explains, has become the centerpiece of his strategic leadership. Robbins embeds dedicated finance professionals alongside revenue-focused teams, helping to fine-tune territory splits, refine pricing, and calibrate product positioning based on real-time data. Now Listen

Tim Arndt still remembers the urgency in the air when AMB Property Corporation decided to merge with Prologis at the height of the financial crisis. It was, as he describes, “a merger of equals,” but Arndt tells us that, in the end, it was the legacy management of AMB that would lead the newly formed Prologis.The “equal” nature of the deal belied a deeper reshuffling of leadership, with AMB's team rising to steer the new entity and Arndt finding himself on the CFO path.Fresh from this integration, Arndt tells us, he learned one of his most valuable lessons: staying agile and raising your hand for new opportunities is critical when your environment is in flux. He found himself immersed in evolving structures, from investor relations to strategic funding, honing a flexible leadership style that balanced risk management with forward-thinking vision.Today, as CFO of Prologis, Arndt credits this experience for shaping his strategic mindset. By leaning into the complexities of merging companies—where cultures, processes, and people collide—he discovered that strong financial leadership isn't just about spreadsheets and metrics; it's about stewarding a newly formed organization toward stability and growth. That early trial taught him to embrace change rather than fear it, which is precisely how he continues to guide Prologis into future opportunities.

It was a moment that would shape Erik Swenson's approach to finance forever. As a co-op student at Northeastern University, he found himself in front of a room full of engineers, presenting financial metrics he had carefully compiled. When the meeting ended, one of the engineers approached him and said, “That was interesting, but it doesn't mean anything to me. I make the product.” The comment struck a nerve. Driving home that evening, Swenson couldn't shake the realization—numbers alone don't drive a business; they need to connect to the people building it.That early lesson in financial storytelling set the foundation for a career built on bridging finance with operations. Swenson tells us his path wasn't a straight line—he originally pursued computer science before pivoting to economics and then accounting. After early roles in financial analysis, he spent 15 years moving through finance leadership positions at Danaher, where he sharpened his ability to translate financial insights into business decisions.When IDT tapped him to be CFO in 2018, Swenson faced a challenge that tested his adaptability. As he tells us, the company had a strong accounting foundation but needed deeper financial analysis to support its innovation-driven growth. He immediately set to work embedding finance into IDT's decision-making, ensuring the function wasn't just reporting numbers but helping shape the company's strategic direction. “It's not just about getting the numbers right,” Swenson explains, “it's about making sure those numbers mean something for the business.”

It was a moment of “shock and awe” that Jason Lee says shapes his strategic mindset. Soon after joining Square, he discovered a major partnership with Starbucks that was quietly bleeding millions of dollars and threatened Square's financial runway. “We had to swarm the problem,” Lee tells us. The team renegotiated terms and preserved the company's stability—a crucial lesson in vigilance and swift action.Lee's path to that pivotal juncture began in investment banking and private equity, where he gained perspective on what makes companies thrive. Years later, as he moved from corporate development into investor relations and financial strategy at Square, he refined his approach to measuring ROI, understanding key business drivers, and aligning capital investment with sustainable growth. During Square's IPO process, Lee learned how investor feedback refines product strategy and strengthens customer relationships.Today, as CFO of Faire, Lee keeps the same principle front and center: gain visibility first. “If you don't know where your money goes, you can't optimize the outcome,” he tells us. This insistence on clear metrics is part of a broader philosophy that financial leaders must do more than simply balance books. They must articulate how each investment—whether for short-term gains or long-term positioning—serves an overarching goal.That pragmatic yet visionary perspective is evident in Lee's readiness to address risk head-on, allocate resources smartly, and engage stakeholders with clarity. In his view, a successful CFO not only safeguards the bottom line but fosters an

The moment 2X secured private equity backing in March 2023, CFO Brandon Sullivan knew expectations would shift overnight. “There's gonna be a press release,” he remembers thinking. “Our new PE partners will open up a treasure chest of relationships for us—we need to be ready.”In anticipation, Sullivan and his team ramped up hiring, ensuring 2X had the supply of talent needed to meet the expected surge in demand. But in the six months spent navigating investment negotiations, pipeline oversight had faltered. Revenue didn't spike as expected. Instead, churn crept up. “We had holes we hadn't paid attention to,” Sullivan tells us. “And the benefits we thought would be immediate weren't—they needed time to take root.”The result? A painful lesson in timing. They had staffed up, but business momentum had stalled, sending gross margin percentages downward month after month. The wake-up call came swiftly—a tough conversation with the PE board. “It was needed,” he admits. “The realization hit: Monthly reporting was too infrequent for a dynamic business like ours.”

Stuart Leung had occupied the CFO office at Flexport for only a few months when he realized the supply chain management company's growing margin pressures stemmed not from a single root cause but from many. From pricing misalignment to invoice errors, Leung had compiled a lengthy list of snags. Along the way, he began empowering the people closest to each issue to drive the necessary improvements. By implementing more than 15 “big rock” initiatives—tracked through monthly reviews—Flexport rapidly identified, tested, and refined solutions. This cross-functional, data-centric effort not only began restoring margins but also created a replicable model of continuous improvement.That turnaround effort, Leung tells us, echoed lessons he learned earlier in his career. As a young analyst at an investment bank, he quickly discovered how fundamental analysis and modeling could uncover hidden risks. Later, private equity taught him the vital link between operational decisions and financial outcomes—a perspective he solidified while leading finance and supply chain for a small consumer brand. When he encountered Flexport as a paying customer, its tech platform so thoroughly simplified his logistics challenges that he became a believer in its end-to-end visibility.

Trintech CFO Omar Choucair is increasingly turning to AI as a strategic advantage—building teams, refining data “plumbing,” and automating time-consuming processes. His strategic mindset, honed by years of thriving in unpredictable environments, drives him to embrace AI as a catalyst for operational efficiency and transformative growth. Choucair tells us that his approach centers on leveraging AI to unlock competitive insights, streamline decision-making, and propel Trintech ahead in the rapidly evolving landscape of finance and technology.

It was an impromptu meeting Gantus will never forget. One day at Tesla, the company's then-President of Automotive, Jérôme Guillen, pulled her aside, whispering about a decision Elon Musk was leaning toward. Guillen—who led the automaker's push for production scale and supply chain agility—believed a different path could better serve the company, but needed someone with operational and financial data at her fingertips. “Let's go talk to him—just you and me,” Guillen said. Standing before Musk, Gantus walked through cost impacts and strategic trade-offs, methodically highlighting why their plan would outperform the existing direction. She recounts feeling a rush of excitement when Musk ultimately changed course, calling it key to her growth.That moment encapsulates Gantus's rapid ascent from Tesla's first corporate FP&A hire to a finance leader shaping billion-dollar decisions. Her approach has always been about embedding finance in day-to-day operations, whether rethinking shift schedules, optimizing inventory, or forging data-driven paths for emerging initiatives. Sitting alongside engineers and factory managers, she became a trusted partner who refused to let finance stay locked in spreadsheets.Today, as CFO of Mytra AI, Gantus carries forward the mindset that made her indispensable at Tesla. She now steers Mytra AI's efforts to secure large warehouse contracts and streamline supply chain workflows, forging growth paths. She's determined to refine her new company's cost structures, champion a culture of close collaboration, and leverage every insight from the operational trenches. It's a philosophy built on pragmatism, strategic thinking, and unwavering perseverance—one that began with a tap on the shoulder, data-driven vision, and a fearless willingness to challenge the status quo.

On this episode of Controllers Classified, host Erik Zhou sits down with Brad Silicani, COO of Anrok, to talk about his journey from Big Four accounting to leading operations at a fast-growing tech company.The discussion begins by covering Brad's transition from audit to client side, and highlights the myriad of roles he held at Dropbox. In his time there he was Controller, tasked with landing a sound revenue recognition method, Head of Tax, focused on developing the right international tax structure prior to IPO, and Treasurer, responsible for managing $2B in cash in a changing interest rate environment. In covering all this, Brad shares how these experiences set him up for success in his current role as COO at Anrok, highlighting why a background in accounting and finance makes him the operations leader he is today.And of course, no modern finance conversation would be complete without tackling the AI revolution. Erik and Brad dig into how automation and AI are reshaping accounting, tax, and treasury functions—not just making processes smoother but fundamentally redefining the role of finance leaders. Whether you're a CFO- OR COO-in-the-making, or just someone who loves hearing behind-the-scenes war stories from hyper-growth companies, this episode delivers sharp insights and great conversation.

Kevin Rhodes recalls one of the earliest lessons in his finance career. “I wanted to understand the business,” he tells us, describing his decision to ride along with a Waste Management truck crew. Clipboard in hand, he meticulously recorded stop distances, tonnage collected, and time spent at each location. By the end of the week, he had compiled a customer-by-customer profitability analysis. The results were clear—routes with clustered stops were highly profitable, while distant, scattered pickups drained resources. When he shared his findings, leadership encouraged him to gather more data. The insights led to an initiative that incentivized sales teams to densify routes, improving efficiency and making Rhodes's business unit one of the most profitable in the region. The approach became a company-wide standard.This hands-on, data-driven mindset has shaped Rhodes's leadership across multiple CFO roles. After earning his MBA at Babson College—while working full-time and supporting a growing family—he stepped into his first CFO position at age 32. Since then, he has focused on transforming finance functions beyond traditional reporting, using analytics to guide resource allocation, operational efficiency, and revenue growth. Now at Extreme Networks, Rhodes applies these principles to simplify complex networking solutions and optimize recurring revenue streams. His career illustrates how finance leaders can drive strategy by immersing themselves in operations, leveraging data insights, and aligning financial decisions with long-term business value.

It began with a tense stretch of weeks that Bill Koefoed tells us he won't soon forget. As OneStream's CFO, he was juggling the details of going public when a small AI startup called DataSense caught his attention. “We didn't even have a formal corporate development function,” Koefoed explains, but he threw himself into researching the opportunity. There were skeptics—some board members questioned the timing, while others worried the acquisition might be too costly.Still, the numbers looked promising, and so did the technology. Sitting in late-night calls, Koefoed listened to DataSense's University of Michigan–trained engineers describe predictive models that could supercharge OneStream's demand forecasting. “Getting that talent on board could pay huge dividends,” he recalls thinking. Even with the looming IPO, Koefoed pressed ahead, negotiating terms while appeasing wary investors.For Koefoed, AI isn't a far-off gamble—it's an immediate strategic lever. By championing technology that marries predictive power with secure financial data, Koefoed tells us he helping steer OneStream toward a future where finance and AI seamlessly intertwine.

It was a puzzle that John Wilson simply couldn't resist. Intel had long sold processors to the federal government on a commercial basis, but the rising importance of High Performance Computing (HPC) demanded a new approach. Undeterred by the maze of federal acquisition regulations, Wilson volunteered to stand up a dedicated government unit, a move that he tells us helped unlock cutting-edge HPC research. The work took him to the edges of “bleeding-edge technology,” even if it also meant navigating the detailed rigors of government compliance.That knack for transformation would serve Wilson well when he later encountered another pivotal moment: the day the moving truck arrived at his new home in Oregon—just as Intel announced the dissolution of the very business group he was joining. Rather than panic, he thrived, moving on to master complex FP&A and business development roles. It was the same mindset that guided him in standing up an entirely separate legal entity to better serve government contracts, broadening his view of finance from purely operational tasks to strategic decision-making.Today, as CFO of Sabey Data Centers, Wilson continues to fuse vision with pragmatism. He has drawn from his HPC experience—where technology evolves at breakneck speeds—to guide Sabey's approach to data center design and expansion. Collaborating with teams to manage billion-dollar investments, he remains resolute on two fronts: balancing the need for innovation with disciplined capital allocation, and preserving a culture of “good stewardship” that ensures long-term stability for tenants ranging from tech giants to smaller enterprises.

It was a phone call Amy Butte tells us she will never forget. Lifting the receiver, she heard the familiar voice of her father—an accountant who had always championed her career. But this time, his words were tinged with a curious mixture of praise and amazement. He simply couldn't fathom how his daughter, who had taken only one accounting class, was now the CFO of the New York Stock Exchange. “Finance leadership is more than numbers,” Butte reminds us, explaining that, for her, success hinges on weaving data into a strategic narrative that shapes decisions.That same flair for bold moves followed her into a pivotal meeting with the NYSE's new leadership. “How'd you like to be the CFO?” she was asked on the spot, an offer so direct it felt surreal. Butte tells us she immediately saw an opportunity to modernize a centuries-old institution, and within two and a half years—half the time originally planned—she was leading the organization's transition to a public company. The accelerated timeline tested her agility, forcing her to rethink legacy processes and overhaul entrenched systems. Through it all, she discovered that being an agent of change meant continuously blending operational discipline with forward-thinking ideas.

In this episode of Controllers Classified, Erik Zhou sits down with Karen Wu, the Chief Accounting Officer at Clari, to discuss the role of accounting in a company's exit strategy. The conversation starts with an overview of Karen's time in Transaction Services at PWC, where she helped a myriad of companies prepare for IPO - including Alibaba, the largest IPO in US history. Drawing on those experiences, Karen covers the reasons why a company may look for an exit, the types of exit strategies, and the role of the accounting team in those strategies.Specifically, Karen speaks to some ‘musts' that accounting teams have to get right no matter the exit strategy - things like closing the books on time, ensuring precision and reliability in financial statements, and being able to comply with public company requirements. She speaks to the IPO readiness timeline, and how companies should approach it not just through the lens of accounting and finance, but across all functions.The conversation then pivots to Karen's time at Clari. She shares her priorities as well as her POV on global accounting processes given the company's international operations. Her number one piece of advice? Don't be hesitant to outsource pieces of work to consultants who may have a better handle on local tax policies.

Ashim Gupta, who has evolved from a pre-IPO CFO to now serving as both CFO and COO, is busy redefining the role of finance in driving growth and innovation. Initially focused on strict financial discipline, Gupta's responsibilities have expanded to integrate long-term growth initiatives with day-to-day operational execution.In our discussion, Gupta explains that funding AI projects at UiPath is guided by a rigorous evaluation framework. “We assess every project based on scalability, efficiency, revenue impact, and strategic differentiation,” he tells us. This disciplined approach ensures that each AI investment not only delivers measurable ROI but also aligns with UiPath's broader vision of merging AI with automation.Transparent communication with the investment community has been key to this evolution. Gupta emphasizes that clearly articulating milestones and performance metrics is essential as the company's narrative shifts from its RPA origins to becoming a leader in AI-driven automation, he tells us. This transparency builds trust and demonstrates the strategic value behind each investment decision.Moreover, Gupta's dual role enables him to balance aggressive AI R&D investments with the demands of core operational priorities. By bridging finance and operations, he ensures that strategic initiatives are effectively executed while maintaining robust financial discipline. As UiPath continues to push the boundaries of automation, Ashim Gupta's strategic mindset remains central to its sustained success and innovation in the evolving digital landscape.

Like many seasoned finance executives, Damon Fletcher saw Snowflake as a game-changer in cloud-based data management. While a senior finance executive at Tableau, he championed its adoption, recognizing its ability to scale analytics and streamline enterprise data operations. But he also discovered a challenge familiar to many finance leaders—the hidden costs that come with cloud consumption-based pricing.At Tableau, Fletcher tells us, the company's Snowflake costs grew exponentially, mirroring a broader trend in tech where companies struggle to control cloud spend. This realization led Fletcher beyond the CFO office. In 2023, he co-founded Caliper, a company dedicated to bringing greater cost transparency and AI-powered efficiency to cloud spending.Fletcher tells us that AI is central to Caliper's approach. The platform leverages machine learning forecasting to predict cloud usage trends and generative AI to surface actionable cost-saving recommendations. Unlike traditional cloud cost tools, Caliper provides deep insights across Snowflake, AWS, and Datadog, allowing finance and DevOps teams to pinpoint inefficiencies in real time.

Early in his career, Lior Maza chose to immerse himself in smaller, venture-backed startups instead of large enterprises—a move that exposed him to an array of responsibilities, from fundraising, recruiting to crisis management. “When you're in a small team,” Maza tells us, “you end up doing everything, and that's where the agility mindset really takes root.”Years later, after honing his skills in larger organizations, he joined Priority Software, an established yet agile cloud ERP firm. Under his guidance, the finance function embraced new performance measurements—focusing on recurring revenue, net retention, and churn—to manage a transition from traditional licensing to a SaaS model. “Agile finance leadership,” Maza tells us, “is about looking beyond immediate metrics and creating frameworks that drive long-term value.”

Bill Korn approaches board leadership with the same strategic, forward-thinking mindset that defined his CFO career. He believes a board member's role extends beyond governance to actively supporting company growth, shaping financial discipline, and guiding leadership teams through inflection points. Bill prioritizes long-term value creation over short-term gains, leveraging his M&A expertise, IPO experience, and global operations knowledge to help companies outmaneuver larger competitors. He advocates for hiring and retaining top talent, using technology as a competitive advantage, and fostering a culture of transparency and accountability—ensuring that businesses not only grow but sustain their success in evolving market conditions.

In this episode of Controllers Classified, host Erik Zhou sits down with Jeff Arensman, Controller at Bloomerang, to cover two important topics: building a finance function from scratch and the role of finance in acquisitions.For Jeff, the two are inextricably linked at Bloomerang. As the first finance hire at the company, his first task was supporting an acquisition that needed to close in just three weeks. He then quickly turned to building a strong foundation for the accounting and finance practice at the company through new processes, tools, and technology. Jeff covers how he spent his time in the first few years at Bloomerang, including how he approached team building, and then turns to his current priorities now four years in at the company (a big NetSuite implementation!).After sharing how he approached building a function, Jeff does a deep dive into considerations during acquisitions both on the buy and sell side. He details his extensive experience in acquisitions and highlights some of his best practices and learnings - including how important it is to add nuance and context to the models that bankers develop during the due diligence process.The episode closes with Jeff sharing the deep detective work he had to do to get to the bottom of one of his weirdest company expense moments early in his career.

For Matt Collis, CFO of PairSoft, storytelling is more than a skill—it's a strategic tool for aligning teams and scaling businesses. Whether leading acquisitions or guiding cross-functional teams, Collis uses financial narratives to clarify priorities and inspire action. “Someone has to be the storyteller,” Collis tells us, emphasizing how framing financial data in relatable terms helps drive organizational alignment and decision-making.Collis' career began in accounting, where he spent seven years honing technical expertise in public accounting. However, he recognized early on that his ambitions extended beyond the technical realm. His transition into leadership roles provided opportunities to engage directly with business leaders, crafting financial strategies that supported operational goals. A pivotal chapter in his career came at Transaction Data Systems (TDS), where he helped the company scale dramatically. Over five years, TDS tripled in size through seven acquisitions, Collis tells us, requiring him to integrate diverse cultures, systems, and processes while scaling the finance team from 10 to 30 members.At PairSoft, Collis leverages these experiences to prioritize purposeful integration. He sees cultural alignment as key to long-term success, noting that acquisitions can falter without proactive efforts to unite teams around a shared vision. His strategic mindset also focuses on transparency and scalability, ensuring that financial strategies align with operational goals and are clearly communicated across the organization.