1114: Building a Smarter Funnel at Speed | Kevin Wall, CFO, Stax Payments

When Kevin Wall first stepped into industry from public accounting, it wasn’t by accident—it was through a client he already knew well. The company, in the midst of an ERP conversion and preparing to go public, saw in Wall someone who understood both their numbers and their needs. “They were familiar with me. I was familiar with them,” he tells us.That early pivot from audit into operational finance set the tone for a career defined by depth over speed. Wall spent 13 years at Alcatel-Lucent and a decade at FIS, climbing steadily while broadening his remit from general accounting to pricing, FP&A, and global finance operations. His longevity at these firms, he tells us, allowed him to “move and see new things under one roof” while growing his leadership footprint.Today, as CFO of Stax Payments, Wall is again stepping into transformation. The company, which serves over 40,000 SMBs and processes more than $20 billion in volume annually, is preparing to launch its own end-to-end processing engine. Wall’s priorities reflect a blend of commercial focus and operational precision: “It’s the top of the funnel,” he says, referencing lead generation, “and speed to revenue.”A self-described servant leader, Wall believes in “clearing obstacles” so teams can grow. That mindset also drove a past strategic move—reorganizing finance functions like billing and AP to other departments. It was a bold step, but one grounded in clarity: “Let’s really define what we want finance to be,” Wall tells us.

When Josh Schauer joined Longview, a Toronto-based software company, he had no idea that a transformative chapter of his career was just a few years away. In 2020, Longview was acquired by insightsoftware—a turning point that brought both uncertainty and opportunity. “It’s kind of equal parts fear and optimism,” he tells us. “You wonder: Am I going to have a job coming out of this?”But his then-CFO advocated for him, making clear to the acquiring company, “they can’t lose you.” That moment, Schauer tells us, “swung the pendulum to the opportunistic side.”Rather than move on, Schauer leaned in—ultimately rising to become CFO of insightsoftware five years later. Today, he leads finance for a company that has completed 31 acquisitions and delivers AI-powered tools for CFOs—tools Schauer uses himself.Early in his career, a mentor CFO gave Schauer full ownership of budgeting, board reporting, and strategic analysis. That experience shaped his belief that finance is “a strategic operating partner.” It’s a mindset that drives his approach today, from implementing daily agile forecasting to integrating AI across functions.“We are an AI-first organization,” he explains, with AI liaisons and company-wide training supporting adoption. Though measuring ROI can be tricky, he sees clear returns in efficiency and insight.Still, he keeps people at the center: “Is the team taken care of? Do they feel engaged?” For a CFO who’s navigated acquisitions and transformation, Schauer tells us, team satisfaction remains one of his top priorities.

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.”