The CFO Role in Scaling AI Curiosity

When Nathan Winters led a supply chain team earlier in his career, he noticed something that would shape his leadership style: “The credibility you get by the operating leaders when they see you out in the field… is incredibly important.” Whether visiting customers, walking a manufacturing floor, or sitting in on operating meetings, Winters found that physical presence fostered trust—and that trust gave finance a real seat at the table.Today, as CFO of Zebra Technologies, Winters continues to emphasize business partnership grounded in proximity to operations. In the four years since he stepped into the CFO seat, Zebra has weathered post-COVID surges, global supply chain disruptions, and enterprise restructuring. The company’s product footprint—often “hidden in plain sight,” from grocery checkout scanners to hospital wristbands—has expanded to include robotics and machine vision, Winters tells us.He’s also broadened his own remit, taking on IT and cybersecurity leadership, including oversight of both the CIO and CISO. In that time, Zebra has reduced China-based production from 80% to 30% and introduced new AI capabilities like “Zebra Companion” to automate shelf management for retailers. Internally, Zebra launched a private LLM instance—“Z-GPT”—to streamline tasks from expense report queries to sales presentations.“Your job isn’t to just close the books,” Winters tells us. “If you’re not analyzing… finding new ways to think about things… you’re getting passed up.” At Zebra, finance is not just a control function—it’s a strategic force embedded in every operational stride.

Nearly a year into his CFO role at Reltio, James Redfern still feels like he’s catching up. “I’ve made some progress, but I’m definitely not where I… need to get,” he tells us. That steep learning curve was exactly what drew him to the company.Redfern didn’t find the Reltio opportunity through recruiters. Instead, it surfaced during a casual conversation with a mentor. “I was actually looking at something else,” he recalls. “And he said, ‘Oh, if you’re looking… I’m on the board of a company that’s looking for a CFO.’” That kind of personal connection—what Redfern calls “psychic safety”—has guided his last two career moves. It’s less about who you know casually, he tells us, and more about “people you actually have worked with.”At Reltio, Redfern stepped out of his comfort zone. After years in application-layer software companies like Workday and PayScale, he shifted into deep IT infrastructure. Reltio’s platform ensures enterprise data is clean and consistent across systems—a need made more urgent by the rise of AI. “You need a reliable, unified view of your data,” he explains. “One customer equals one customer—not three different customers in three different systems.”With 190 customers and $160 million in annual recurring revenue, Reltio works with some of the world’s largest enterprises. The company’s mission, Redfern tells us, is to replace legacy systems like Informatica and IBM with cloud-native data unification at scale.For Redfern, the attraction wasn’t the title. It was the challenge. “This is the kind of journey I committed myself to,” he says.

How are finance chiefs steering the AI revolution? In this fast-paced special edition of CFO Thought Leader, host Jack Sweeney spotlights Packer Fastener CFO Brian Hogeland and LinkedIn’s top AI voice Allie K. Miller. Together they unpack why 2023’s “just try ChatGPT” mantra is obsolete, how agent-orchestrated systems will reshape mid-market operations, and where cash-savvy CFOs can safely place AI bets today. Tune in for fifteen minutes of practical insight, provocative foresight, and career-defining guidance.

Amanda Whalen’s first unit CFO role began with a question. “You’re not a finance technical person,” her company’s president told her, “but you’re the strongest leader on my team. Will you be willing to be the CFO and help me transform the finance function?” She accepted.Over the following year, Whalen tells us, her team tackled three major initiatives: fixing broken cost accounting at a dairy plant, realigning sales incentives to drive margin, and overhauling the P&L reporting structure to match the new parent company’s expectations. The team was skeptical—“They said, ‘You’re crazy. There’s no way we can do that all in a year,’” she recalls. But they did. The business became 10% more profitable.That experience, Whalen tells us, revealed finance as a powerful lever to drive business transformation—“You get to work with every function… It’s highly quantitative and analytical, and it involves working with a lot of really great people.”Now CFO at Klaviyo, Whalen brings the same philosophy. In three years, the company more than doubled revenue and improved margins by 20 percentage points. She led Klaviyo’s IPO, expanding the company’s readiness across technical, strategic, and investor-facing dimensions. “It wasn’t just about getting ready to go public,” she says, “but about operating successfully as a public company for a long, long time.”Whether transforming legacy operations or scaling a fast-growing SaaS firm, Whalen’s approach remains constant: think long-term, go deep into execution, and “be kind to your future self.”

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 the evolving role of FP&A as a driver of organizational agility. Across the board, Brett sees finance leaders striving to balance innovation with caution in a way that positions their teams for scalable growth.

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.