CFO THOUGHT LEADER

In her second week as CFO, Cristina Kim sat with Octaura’s leadership team reviewing a three-year strategy and ambitious 2026 targets, she tells us. As the numbers appeared on the screen, her instinct was to do what she had done for nearly two decades: probe what might go wrong, stress-test assumptions, and look for what could break, she tells us. Mid-meeting, she experienced what she calls an “aha moment”—realizing she was no longer outside the story but inside it, responsible for helping the team achieve those goals, she tells us.

That shift caps a career built on breadth rather than a linear ladder. Cristina began in investment banking in Hong Kong before spending 17 years in JP Morgan’s strategic investments group across London and the United States, she tells us. There, she learned to sit at the center of technology innovation, translating between business needs, risk, and upside, and working closely with management teams and CFOs, she tells us. Over time, investing in Octaura and partnering with its leaders made her want to move from evaluating companies to helping build one, she tells us.

Today at Octaura—an electronic trading platform and data company focused on loans and CLOs, she tells us—Cristina is applying that investor muscle in new ways. She is building frameworks for resource allocation, pushing for more granular, week-to-week metrics, and exploring how AI-enabled forecasting and internal data tools can sharpen decisions, she tells us. The discipline remains, but now it is in service of writing the story from within, she tells us.

The morning after Airbase’s sale closed, Aneal Vallurupalli woke up to a very different org chart. Before the deal, roughly a third to almost half of the company reported to him, including onboarding, professional services, account management, customer success, and financial services revenue, he tells us. The day after, those teams rolled into the acquirer and “I have my EA reporting to me. And that was it,” he tells us. It left him thinking, “wait a minute… I’m not making any decisions anymore,” he tells us.

That jolt became a pivot point. Rather than chase another title, he went looking for roles where finance could architect the whole engine—customer journey included. It’s the same instinct that once led him to peel back Airbase’s retention problem: starting with GRR by segment, then listening to Gong calls and mapping every step from contract signature to renewal, he tells us. Retention, he concluded, is almost never a single-issue story.

Today, four weeks into his CFO role at Drata, it already feels like “the third quarter operating” there, he tells us. He talks about “ruthless prioritization” as a muscle first trained in high-level tennis and investment banking, where time, not money, was the real constraint.

Now he wants finance to be the company’s best “so what” team—not just reporting variances, but offering an informed view on what to do next. Even with AI, he is wary of “tool proliferation” and scattered agents, arguing that every business must choose deliberately what sits centrally on its data and what remains at the edge.

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 simplified his logistics challenges in such a way that he became a believer in its end-to-end visibility vision.

In this special retrospective episode, we revisit three standout conversations from our archives to explore how automotive CFOs have long shaped strategy inside some of the industry’s most complex business models. From auctions to dealerships to early-stage EV manufacturing, these finance leaders reveal how they navigated scale, technology shifts, and operational risk. KAR Auction Services CFO Eric Loughmiller discusses turning massive transaction data into intelligence. Warren Henry Automotive CFO Erik Day explains the realities of margin compression and liquidity pressure. And former Electra Meccanica CFO Bal Bhullar shares how finance guides a young manufacturer from prototypes to production. Together, their insights form a timeless lesson in CFO leadership at high speed.

The email with the term sheet arrived first, then the bottle of champagne from the CEO, Jayme Brooks tells us. The lender had agreed to a nontraditional structure that allowed Capstone to borrow against intangible assets, creating a lifeline at a moment when revenue had dropped about 40% and market cap had fallen from roughly 400 million to 25 million, she tells us. Cost reductions, including a 25% reduction in force and ultimately a 50% cut in the cost structure, followed, she tells us. But the bridge financing meant the company could still fund payroll, buy supplies, and keep shipping microturbines.

That moment caps years of learning “in the room.” Brooks began in engineering before shifting into accounting and public practice, she tells us. Controller roles in aerospace and a UK-owned division exposed her to debt, private equity, and board dynamics. She later accepted what looked like a step back—a director of financial reporting role at an unprofitable public company—because she wanted capital-markets experience and trusted a former CFO mentor, she tells us.

Along the way, an MBA and countless investor calls broadened her view beyond “head down” execution. In the restructuring, she focused on explaining the “why” to suppliers, employees, and investors, securing payment plans and shared sacrifice so the business could survive, she tells us. Today, at Limbach, she continues to leverage external experts, integrate acquisitions, refine owner-direct metrics, and lead with an empathetic, trust-building style inspired in part by Leading with the Heart, she tells us.

Jack Welch’s binder hit the floor before Michael Bourque had time to react. At just 23, he sat in a Honeywell acquisition review meeting as the “keeper of the numbers,” rifling through a binder he knew didn’t contain the EPS detail Welch demanded. When the answer didn’t come, Welch “swept his binder off the table, threw it across the room, and got up and left,” Bourque tells us. The moment stayed with him—not only the need to anticipate every question, but the feeling of “how I was treated,” a lesson he carried forward.

That early scene captures the intensity of Bourque’s 15 years at GE, where he rotated every four months on the corporate audit staff, learned to understand a business model quickly, and moved across countries from Mexico to Italy to Canada. He tells us those experiences became “a massive accelerator” but also showed him what he did not want: senior lives “lived 90 days at a time.”

Leaving GE led him into Ocwen, where regulatory pressure mounted immediately. Advisers warned him to “run for the hills,” yet he stayed, tracking cash daily and absorbing public blows from the New York DFS. The experience, he tells us, taught him “how to navigate a crisis and try to keep your cool.”

At LendingHome (later Kiavi), he applied that calm to redesign the business around two customer cohorts—first-timers and professionals doing “eight or more” flips a year—and anchored decisions in unit economics. That discipline would shape his leadership at Convera, where he now steers a global payments network and pushes teams to adopt AI tools that “help them… get clarity on that next operational step.”

In this episode of Planning Aces, we spotlight FP&A insights from three CFOs leading innovation with discipline: Chris Sands (InvoiceCloud), Steve Sutter (Celigo), and Niels Boon (Cint). Each shares how finance is shaping AI, go-to-market models, and data-driven transformation without losing rigor. From building an “AI Ops” function and embedding finance in sales strategy, to piloting AI tools in small, staged experiments, these leaders treat innovation as a managed process. Our resident thought leader joins to connect the dots, emphasizing structure, clear metrics, and portfolio thinking as the new essentials of FP&A.

We’re excited to welcome author and former CFO Glenn Hopper into the co-host seat. Glenn joins us as our resident thought leader, bringing a deep well of experience at the intersection of finance, technology, and AI. We’re thrilled to have his voice and perspective guiding this next chapter of Planning Aces.

Chris Sands leans into organizational design, reallocating talent into a formal AI Ops team and emphasizing change champions.

Steve Sutter focuses on commercial mechanics, tying FP&A to sales economics, talent mix, and scale-up guardrails.

Niels Boon emphasizes risk-staged innovation, using small pilots for operational wins while ring-fencing bold synthetic-data bets as long-horizon R&D.

When Troy Anderson accepted the CFO seat at Kelly Services in 2024, he stepped into an organization that, as he tells us, “had done a number of acquisitions … and really invested in the business.” The legacy staffing firm had spent nearly $1 billion to expand its reach but had yet to fully integrate those pieces. Anderson’s mission: align a global operation that had grown faster than its systems.

It was a familiar challenge. Across three decades and multiple industries, Anderson has made a career of steering companies through transformation. At Universal Technical Institute, he led a finance overhaul that supported a business which, he tells us, “more than doubled the company.” Before that, as a senior finance leader at Xerox and its services spinoff Conduent, he helped raise $2 billion in debt and “build out the public company infrastructure … from scratch.” That experience, preceded by an investor-relations rotation where he worked directly with Xerox CEO Ursula Burns and CFO Kathy Mikells, became “the game changer” that propelled him toward the CFO office.

Now, at Kelly, Anderson is guiding a transformation “on both sides of the ledger … organizational and technology.” He’s integrating recent acquisitions, modernizing finance systems, and preparing the company for the cyclical realities of a staffing industry he describes as “in decline for about two years now.”

His approach reflects a pattern consistent throughout his career: when others see complexity, Anderson sees structure waiting to be built—and an opportunity to apply every lesson learned from the transformations that came before.

When David Lee joined PG&E in San Francisco, the company was collapsing under the weight of California’s first energy crisis. “These utility veterans kind of got us into this,” the new CFO told him, handing him an unusual assignment: act as an “anti-CFO.” Lee spent his days testing every forecast and financing plan, proposing contrarian options like a preferred-equity line from KKR. The exercise, he tells us, forced him to “think independently” and learn how to guide a public company in deep trouble.

That moment crystallized a pattern in Lee’s career—a willingness to enter complex situations and rethink accepted wisdom. From his start at Leo Burnett Company, where he learned to “walk in the shoes of the consumer,” to his nine-year transformation tour at Del Monte and later Best Buy’s celebrated “Renew Blue” turnaround, he has sought environments that reward original thought over routine expertise.

Today, as global COO and CFO of Webtoon, Lee applies the same mindset to a different kind of transformation—the business of storytelling. He tells us the platform connects 24 million creators to 156 million readers each month, growing its English-language audience 19 percent year over year. Yet he draws a bright line around technology’s role: “Human storytellers are the best storytellers.” AI, in his view, should fight piracy and improve discovery, not replace creativity.

Across every chapter, from crisis utilities to digital comics, Lee’s philosophy remains constant—progress begins when finance leaders question assumptions and listen long enough to see possibilities others overlook.

When Erik Wissig recalls his early years as a founder, one moment still stands out. The team had met its growth goals and earned their bonuses—but the company’s cash flow hadn’t caught up. “You need the cash to make those payments,” he tells us. That hard-won lesson reshaped how Wissig approached finance from that day forward: plan ahead, balance ambition with liquidity, and bring the wider leadership team into that awareness.

Before that turning point, Wissig had spent a decade in investment banking, advising hundreds of middle-market companies on transactions. Eventually, the advisor wanted to build. In 2013, he co-founded Hixme to give employers a new way to fund individual health insurance—an idea born from the Affordable Care Act’s reshaping of the market. When regulatory realities slowed progress, Wissig stayed the course. Hixme’s platform and team were acquired by SureCo in 2020, where he now serves as CFO and COO.

At SureCo, Wissig’s banking discipline meets an operator’s pragmatism. He focuses on two levers—raising revenue per customer and scaling efficiencies—and on hiring into his weaknesses, surrounding himself with strong CPAs. His leadership style mirrors his philosophy on failure: persistence is progress. “If the game is still being played, then you haven’t failed,” he tells us.

Twelve years into his pursuit of the ICHRA model, Wissig remains motivated by one conviction: lasting change in healthcare begins by putting individuals—not institutions—at the center of the system.