1150: Making AI Practical in Finance, Not Theoretical | Matt Novick, CFO, Triplelift

Matthew Novick traces one of his earliest business lessons not to a boardroom, but to a furniture store in Portland, Maine. Growing up in his family’s business, he learned how to read credit reports, price products, and assess who was “credit worthy,” skills that showed him how decisions affect a business long before he ever closed a set of books, Novick tells us.That operational grounding followed him into finance. Early roles at IBM and AOL put him on both the expense and revenue sides of the P&L, including sales operations and compensation design. Those experiences shaped his belief that finance is not just about counting dollars, but understanding what the numbers actually mean, he tells us. “If you don’t understand what goes into closing those books… you’re never actually going to understand your business,” he says.Read MoreHis path accelerated quickly. After leaving AOL, Novick joined Magnetic, where he became VP of Finance and then the company’s first CFO in his early 30s. Since then, he has moved through multiple CFO chapters across ad tech and data-driven businesses, refining how he partners with CEOs. That partnership, he explains, is central—so central that he once flew across the country to spend two days with a CEO before accepting a role, Novick tells us.A defining strategic moment came at PlaceIQ, when the company received an unexpected inbound acquisition inquiry. Preparing to assess synergies, unit economics, and whether “one plus one really equals three” reshaped how he thinks about strategy and readiness, Novick tells us. Today, as CFO of TripleLift, that mindset carries forward—pairing operational fluency with disciplined decision-making in an increasingly complex, AI-influenced finance landscape.

At 19, working part-time in a bank branch while attending college, Ed Hagan made a simple recommendation: expand the branch. The idea was taken seriously enough that he was transferred to the bank holding company’s finance and accounting department, where he suddenly found himself helping with acquisitions, preparing board materials, and contributing to an IPO. The exposure was far greater than he expected at that age, Hagan tells us, and it sparked a curiosity that would shape his entire career.That early experience with real-world complexity led him to KPMG—then Pete Marwick—because the firm audited the bank. There, he spent roughly 20 years, including a decade as partner, learning “every day” and taking on global finance transformation work. When the consulting arm later separated into BearingPoint, Hagan continued building capabilities, eventually moving to London to grow a financial services practice from just a few people to a couple hundred.After 21 years in consulting, he felt ready for a different kind of problem-solving. He joined a private-equity and family-office environment, then built a fractional CFO and outsourcing practice that connected him with growth-stage founders. One of those clients—Satisfi Labs—would draw him back into the intersection of finance and technology.Satisfi Labs, Hagan tells us, is an agent platform designed for live experiences like sports, entertainment, and tourism. The company blends proprietary technology with LLMs such as OpenAI and Gemini, packaging them into solutions that make “AI hireable.” Today, the platform supports about two-thirds of North American professional sports teams and continues expanding across venues, theme parks, museums, and tour operators.

At first, we wondered why Zane Rowe was once again leading us back to Continental Airlines. With notable CFO tenures at VMware and EMC—chapters rich with transformation—surely there were fresh stories to surface.But as Rowe began tracing the logic behind flight profitability, route modeling, and data-rich decision making, the relevance snapped into focus. His Continental experience isn’t just a recurring anecdote; it’s the lens through which he still interprets complex systems today. That early foundation made this discussion every bit as insightful as our last—especially as he connected those lessons to Workday’s AI trajectory and the accelerating pace of strategic decision making.“I spent a lot of time in the airlines in what we called flight profitability,” Rowe tells us. At Continental, he helped build systems to understand which routes truly created value when full planes were still losing money, he tells us. That work, grounded in heavy telemetry and EMC technology, showed him how finance could move from reporting results to reshaping the route portfolio, he tells us.In his first conversation with CFO Thought Leader, Rowe walked through those early chapters—from revenue management at a post-bankruptcy airline to a bold sales pivot at Apple and multiple CFO roles in technology, he tells us. In this second interview, he returns to the same storyline but takes it one step further, drawing a direct line from that profitability model to today’s AI-driven world, he tells us.Now, as Workday’s CFO, he describes AI as an equalizer that lets small teams run multiple forecasting models and ingest far more variables in cash projections than before, he tells us. He points to “Everyday AI,” a company-wide initiative, and a cross-functional AI leadership group that pushes common tools, responsible use, and regular check-ins on what is changing in the work itself, he tells us.Rowe’s finance strategic moment this year is “recognizing the importance of investing more into AI”—organically and inorganically—because peers are not standing still and customers want those capabilities, he tells us. With a total addressable market “in the hundreds of billions of dollars” and revenue “much less than that,” he frames leadership now as deciding where to lean in hardest, he tells us.

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.