CFO Thought Leader

Fiber is “a lot of investment up front for that stream of cash flow in the future,” Derek Doyle tells us. At C Spire, that reality defines nearly every strategic decision.The advanced technology and communications company has been reinventing itself for more than 70 years, Doyle tells us. Today, it is the largest privately held wireless carrier in the U.S. and operates 22,000 miles of fiber, placing it among the top 20 fiber internet providers in the country by premise passings, he tells us. The company has invested hundreds of millions of dollars expanding beyond Mississippi into Alabama, Tennessee, and Florida, Doyle tells us—moves that require disciplined capital judgment.For Doyle, capital allocation is not just about near-term profit. It is about equity value. Public companies may emphasize shareholder return metrics, but as a private company, C Spire centers on equity value growth, he tells us. “I'm a big intrinsic value person,” Doyle explains, grounding decisions in discounted cash flow and intrinsic value models, he tells us.That approach requires looking beyond projected profit to the full funding equation—how much must be borrowed, how much capital deployed up front, and what long-term cash flows justify the investment, Doyle tells us.Ultimately, the objective is clear: invest resources in what “drives that needle the most,” he tells us—ensuring that growth in connectivity translates into sustainable enterprise value.

In this episode of Planning Aces, CFO Kevin Rubin of Zscaler, CFO Bruce Schuman of Universal Technical Institute, and CFO Razzak Jallow of FloQast share how disciplined FP&A leadership is shaping AI adoption. Rubin frames AI as a capital allocation exercise governed centrally to prevent tool sprawl. Schuman stresses foundational readiness—data governance, ERP consolidation, and process redesign—before deploying AI-driven forecasting. Jallow cautions against fragmented “spaghetti AI,” advocating for platform coherence and skill development. Together, they reveal that AI success in FP&A depends less on speed and more on governance, architecture, and trust in the planning process.

Nearly 90% of Americans suffer from metabolic disease, Manu Diwakar tells us, citing a recent McKinsey & Company study. For Diwakar, CFO of Virta Health, that statistic defines both the scale of the challenge and the clarity of the mission.Metabolic disease, he explains, includes type 2 diabetes, obesity, liver disease, kidney disease, heart disease, and high blood pressure—“branches of a tree,” he tells us, all sharing the same root cause: poor nutrition. Virta's model blends medical professionals and technology to reverse those conditions, partnering with insurers, employers, and government entities in a B2B2C framework.From a finance perspective, the impact is measurable. Diwakar tells us Virta uses pharmacy and medical claims data to compare enrolled members with non-enrolled employees who share the same conditions—creating what he describes as a “really clean A/B test.” For type 2 diabetes, the company delivers a “two-to-one ROI,” he tells us, making the value proposition tangible.In a market captivated by GLP-1 drugs, the numbers sharpen further. Virta charges about $150 per month, Diwakar tells us, compared with roughly $1,000 per month list price for GLP-1s—about $500 after rebates. More important, he notes that when patients stop GLP-1s, weight often returns. By targeting the root cause—nutrition habits—Virta aims to make results sustainable and long-lasting, he tells us.For Diwakar, disciplined measurement and root-cause thinking align strategy with impact—improving health while lowering cost.

Before his first cup of coffee, Alex Melamud opens Slack—not to scan revenue charts first, but to read customer feedback. “The first one that may surprise you as a CFO that I look at is actually NPS,” he tells us. At Engine, every survey drops into a shared channel so “every executive can see” what customers said, he tells us.That habit fits a finance leader who didn't grow up in the CFO seat. Melamud started in investment banking and then spent 16 years in private equity, learning to build theses, chase signal, and “sell… the product of private equity,” he tells us. Sitting on boards, he watched the CFO role evolve from “corporate governance accounting” into “executive first and maybe CFO second,” he tells us—someone who can talk like product, sales, or operations and earn board trust.Engine became the moment he stepped inside. After leading the company's round “18 months ago,” joining the board, and helping with a CFO search, he looked at founder “Eli” and asked, “what if I joined you as CFO?” he tells us. The draw was a focused mission: serving SMB travel, where customers book “like a consumer” and lose corporate rates and visibility, he tells us.Now his investor lens shows up in the unglamorous work. During annual planning, he dug into the “top 50 costs” outside headcount and pushed leaders to treat each contract “as a brand new relationship,” he tells us—an inspection that produced “10, 15%” savings and “tens of millions of dollars,” he tells us.

On her first day as CFO at Greenphire, Sue Vestri sat in a conference room “learning all of the acronyms” of the clinical trial industry, she tells us. There were “many, many, many,” she recalls, and she listened to the sales team outside her door to understand how the product was positioned and why it mattered.That willingness to learn from the ground up defines her career. Earlier, a mentor warned her she would stagnate if she stayed in the safety of a large company. “You've got to go to grow,” he told her. She left for a 100-employee cloud software firm, a decision that launched a string of growth-company chapters, transactions, and ultimately multiple CFO seats.At Greenphire, she joined when the company had roughly 72 employees and “very low double digit revenue,” she tells us. Under private equity ownership, it expanded globally, shifted from clinical sites to big pharma customers, and supported the Pfizer clinical trial during COVID. Sue and her CEO conducted “20 or 30 presentations” during a remote exit process, she tells us.Today, as CFO of CRIO, she describes finance as embedded in the business—not “sitting behind a desk… producing financial statements.” Her filter for AI is deliberate: avoid the “shiny object” and invest in what is “truly transformational,” she explains. Whether evaluating predictive revenue indicators or AI tools, Sue's throughline remains the same—grow, but with discipline.

In his early 30s, Guillermo Lopez walked into finance as an outsider. “Nobody was giving me a chance in finance because I was an engineer,” he tells us. Then a boss took “a risk” and moved him into a finance role—partly because he was “good with numbers,” and partly because his consulting background meant he could be put “in front of…external parties,” Lopez tells us.That entry point set the tone for how he builds a career: intentionally and with breadth. At American Express, he moved across businesses and finance roles on purpose, because “it's important to get breath, especially if you're thinking about a CFO,” he tells us. Over time, he came to describe himself as “very data driven”—the “non emotional part of the decision making,” he tells us—while also learning to make decisions with “imperfect information” in global roles, he tells us.A later inflection arrived after Visa acquired Tink. Lopez became “the grown up” Visa sent to Stockholm, commuting from London each week, he tells us. The environment was smaller, faster, and short on big-company support. It was “daunting,” he tells us, but it taught him to move quickly, focus on priorities, and take bigger career risks.That same blend—speed and discipline—shows up in his definition of finance's strategic role: being embedded in investment and capital-allocation decisions with data in hand, Lopez tells us.His proof point comes from an earlier chapter. In an international CFO role, he helped reframe how a business allocated “close to $700 million a year,” building ROI insights that pointed to “$30 million more of revenue every year,” he tells us.

An employee is on vacation in the mountains when it happens: “I left my laptop at home.” Instead of scrambling, the employee logs into a virtual desktop from another device, pulling up what looks and feels like their own PC, delivered through the cloud. That simple moment captures how Steve Shimizu describes Omnissa's mission—helping companies enable a digital employee experience that allows people to work from anywhere, on any device, he tells us.For Shimizu, this practical use case reflects a broader evolution in end-user computing. What began with desktop computers moved to laptops and mobile devices, and now extends to “everything” that consumes data—from retail scanners to cars, Shimizu tells us. Omnissa operates at that expanding edge, supporting both physical and virtual endpoints while helping employees stay productive regardless of location.That same blend of flexibility and discipline shapes how Shimizu thinks about the company's growth. Although Omnissa emerged from a carve-out, he resists the startup label. Running a multi-billion-dollar organization with thousands of employees is more like earning a pilot license and being handed a “747” as your first plane, he tells us. Growth matters, but only when paired with financial stability—what he calls “profitable growth.”Finance plays a central role in that balance. Shimizu explains that real partnership comes from moving beyond surface-level metrics and “double-clicking” into the data until it becomes actionable. Just as importantly, finance must revisit those decisions, measuring what worked and what didn't, to guide the company through its next phase of transformation, he tells us.

As he nears the end of his first 100 days at Nintex, Burt Chao is doing something many new CFOs resist: listening more than talking. Understanding the business, its people, and its real growth potential comes before dashboards or directives, he tells us.Chao describes Nintex as a company with a “long and rich history” of helping organizations automate mission-critical work, but one now entering a new season. That evolution centers on orchestration—whether AI-enabled, agent-based, or rooted in RPA—while remaining clear-eyed about identity. Nintex, he explains, will not “become an AI company.” Instead, it aims to help customers leverage AI deliberately, embedding it where it strengthens the foundation of their operations, he tells us.That emphasis on fundamentals shows up quickly in how Chao evaluates performance. In today's environment, “there's no more important number than growth,” he tells us. Margins, profitability, and even rule-of-40 metrics only make sense once leadership understands what growth is possible and how it can be accelerated. Benchmarks matter, but only as tools; every business must be understood on its own terms, he tells us.That discipline has shaped some of the most challenging moments of his career. Chao recalls “shrink to grow” decisions—walking away from investments that still produced revenue but no longer delivered the best return. Those moments are rarely spreadsheet problems alone. They are emotional, cultural, and deeply human, requiring influence rather than authority, he tells us. For Chao, that balance—grounding strategy in numbers while leading people through change—defines the modern CFO role.

The lesson arrived abruptly in a boardroom in Battle Creek. After months of analysis, charts, and market data, the president of Kellogg's cereal division looked up and said, “That's all interesting. I just don't know what to do with it,” Dean Neese tells us. The comment landed hard. It forced him to confront a blind spot early in his consulting career: insight without action is inert.Neese and his team went back, rebuilt the presentation, and returned a week later with clear recommendations tied directly to decisions, he tells us. That moment rewired how he communicates to this day. Every deck now starts with the message and earns credibility with data, not the other way around.That discipline carried forward as Neese moved from consulting into operating roles. At DocuSign, he chose to run both corporate development and integration so there would be no ambiguity about outcomes, he tells us. Strategy, in his view, only becomes real when someone owns the consequences. Living and working overseas reinforced that belief, teaching him that even the best analysis fails if it ignores cultural context, he tells us.Today, as CFO of Placer.ai, Neese applies those lessons through capital allocation. He often asks to see the budget before the strategy document because “where you're spending the money” reveals true priorities, he tells us. Drawing on research involving 400 executives, he points out that top performers make roughly twice as many major decisions each year as underperformers, he tells us.From a single uncomfortable moment at Kellogg's to scaling a data-driven company, Neese's career reflects a consistent principle: finance creates value when it accelerates decisions, clarifies tradeoffs, and turns insight into action.

This special episode of CFO Thought Leader explores how finance leaders develop not through authority or technical brilliance, but through moments that reveal emotional intelligence. Drawing on recent conversations with Kevin Rubin, Toby Driver, and Bruce Schuman, the episode highlights a consistent pattern: leadership is forged through judgment, empathy, and self-awareness when stakes are high and answers unclear. Structured in two parts, the episode first examines formative moments that reshaped how CFOs think, featuring Shelagh Glaser, John McCauley, and Joe Euteneuer. It then shows how those lessons are applied in practice—through difficult decisions, organizational change, and trust-based leadership under real pressure.

The accounting team at Looker showed up every day knowing their jobs might disappear within a year. The company was in limbo—acquired by Google but still waiting on European approval—so the deal hadn't closed, integration hadn't begun, and uncertainty hung over the office. Yet the team continued to deliver “absolutely excellent work,” taking pride in their craft even when the upside had faded, Razzak Jallow tells us.That moment stayed with him. For Jallow, now CFO of FloQast, it crystallized a belief that professionalism and pride are not situational—they're intrinsic. “We get to choose what we do,” he says, reflecting on how the team's attitude revealed character when incentives were stripped away. It's a lesson that echoes throughout his career, from Adobe's subscription transition to Apple's sales finance organization and into his first CFO role.At FloQast, that mindset shows up in how he approaches scale. Early on, the work was about fixing what was directly controllable—the “low-hanging fruit,” as he puts it. Over time, the challenge shifted. As teams and systems matured, the hardest problems required multiple functions to change together, Jallow tells us. Speed gave way to coordination; individual fixes gave way to shared ownership.The same discipline shapes how he thinks about growth. Efficient growth, in his view, starts with customer value, not the P&L. If teams are investing in the highest-ROI initiatives for customers, the financial results will follow—“maybe not in three months… but certainly long term,” he tells us.Whether navigating acquisition limbo or platform expansion, Jallow's throughline is clear: strategy is built on judgment, culture, and pride in the work—especially when no one is watching.

At 18, while many of his peers were heading off to university, Toby Driver made a different choice. He joined an accounting practice through an apprenticeship, a decision driven by his desire for a “quick learning curve” and real exposure to business, he tells us. From the outset, he was less interested in credentials than in understanding how organizations actually work.That instinct carried him through years in audit and into transaction services, where he learned to dissect businesses at speed. In deal advisory, Driver was tasked with getting “under the nuts and bolts” of companies, performing financial health checks with significant value at stake, he tells us. The work sharpened his ability to spot value drivers—but it also revealed a blind spot he wouldn't fully appreciate until later.That realization came after he moved into operations at Ideagen. Leading M&A integrations end-to-end meant sitting with the CEO and C-suite to align sales, product, technology, and culture. Bringing two organizations together was far more complex than it ever appeared from the advisory side, Driver tells us. The experience reshaped his mindset, pushing him to think “business first, rather than necessarily finance first.”As Ideagen scaled from roughly £50 million in ARR to five times that size, Driver faced another inflection point. The company reorganized into regional operating units to restore accountability and clarity, a change finance helped design, he tells us. Today, he carries those lessons forward as CFO—focused on structure, transparency, and creating an environment where people surface issues early. “Bad news never gets better with time,” he says, a principle that now defines both his leadership style and his approach to scale.

When Kevin Rubin arrived at Zscaler in May 2025, he joined an established organization following the retirement of the company's longtime CFO, taking responsibility for continuing the work of a finance leader who had already built a strong foundation. Rubin describes stepping into a business with scale, experienced leadership, and a customer base that included some of the world's largest enterprises, he tells us.In explaining what Zscaler does, Rubin walks through the company's core idea: zero trust. Traditional cybersecurity, he says, relied on network-centric “castles and moats,” requiring large amounts of equipment to connect people, applications, and data. Zscaler challenged that model by treating the internet as a “superhighway” and applying a principle of minimal access. If an employee wants to use Salesforce or email, Rubin explains, the system first authenticates the user and then limits access to only what that person is authorized to see, he tells us.Zscaler was founded in 2007 and went public in 2018, Rubin tells us. Today, roughly 40 percent of the Global 2000 and about 45 percent of the Fortune 500 use the company's platform. Rubin attributes that adoption to a model that delivers security with less overhead and infrastructure than traditional approaches, he tells us. At its core, he says, cybersecurity comes down to two problems: stopping malicious activity from entering the network and preventing sensitive data from leaving it.Reflecting on his first 100 days, Rubin says the transition was shaped by continuity and people. He describes a welcoming executive team and an organization already positioned for growth. Cybersecurity, he notes, remains a dynamic market, with new vulnerabilities constantly emerging, and staying ahead of those threats continues to define the work ahead, Rubin tells us.

At Intel, Bruce Schuman remembers walking into a meeting as a controller, proud of a product change his team had worked on “for months.” Then CFO Andy Bryant asked one question—one that reframed the proposal around customer impact. “Nobody had thought about (it),” Schuman tells us, and that question “completely changed the entire conversation,” leading to a “10 times better” outcome.That moment captures why Schuman spent “two decades plus 27 years” at Intel, he tells us. Rotational roles pushed him into new challenges every few years, while leaders modeled what influence and partnership looked like in practice. Intel even had a term for it—“constructive confrontation,” Schuman tells us—encouraging finance leaders to put difficult issues on the table in service of better decisions.When Schuman later moved into CFO roles outside Intel, he carried that mindset with him. FP&A, he says, should not simply “report the score of the game,” but act like “people on the field literally changing the outcome of the game,” Schuman tells us. That expectation shaped how he built finance teams and approached decision-making in smaller, faster-moving organizations.Today, as CFO of Universal Technical Institute, Schuman applies those lessons to a mission-driven business focused on workforce development. UTI works with “about 35 OEM partners” and “about 6000 employer partners,” Schuman tells us, and measures success through “70% graduation rates” and “about 85% placement rates,” Schuman tells us. Growth remains disciplined: “We'll never sacrifice student outcomes,” he tells us, even as the company plans to build “anywhere from two to five campuses a year for the next five years,” Schuman tells us.

When Drew Laxton looks back on the past year at Outreach, one moment stands out—not a transaction, but a plan. The company set its annual targets, executed against them, and then exceeded expectations. “When you see green numbers at every quarterly all-hands,” Laxton tells us, “it's amazing how that little bit of momentum just builds the company.” What surprised him most was the cultural impact: morale rose, confidence compounded, and belief followed performance.That belief didn't happen by accident. Laxton's career has consistently positioned him at the intersection of numbers and narrative. He began in investment banking, where he learned early that finance only matters if people can retain the story behind it. “If you can't tell the story, it just stays there,” he tells us. That mindset carried him from banking into operating roles, and later to Apptio, where he experienced nearly the full corporate lifecycle—from IPO preparation to public markets and eventually a private-equity take-private.Serving as Chief of Staff during Apptio's Vista ownership pushed him beyond traditional finance. The role, he explains, was about making sure the CEO “didn't run into a locked door,” anticipating decisions and asking the questions leadership would need answered. That experience sharpened his instinct for alignment.Today, as CFO of Outreach, Laxton applies those lessons through planning discipline, FP&A embedded in the business, and storytelling that connects strategy to execution. Finance, in his view, is not a back-office function—it is the force that helps people understand why the company is moving where it is going.

In this Planning Aces special episode, CFO Thought Leader brings together three finance executives operating in very different industries—but facing remarkably similar planning challenges. David Lee of WEBTOON, Cristina Kim of Octaura, and Zane Rowe of Workday share how FP&A has evolved from a periodic planning function into a continuous decision system. Across global consumer platforms, fintech infrastructure, and enterprise software, each CFO explains how they use leading indicators, forecasting discipline, and real-time data to guide resource allocation. The conversation highlights how modern FP&A enables faster learning, sharper prioritization, and disciplined adaptability in an environment defined by rapid growth and accelerating change.

In his late 20s, Jorge Pliego found himself financing a major expansion in Mexico—not by calling corporate for cash, but by rethinking the entire structure. At Procter & Gamble, he was given the chance to fund a new paper products facility locally, navigating tax and financing incentives until the deal carried “zero” interest cost, Pliego tells us. Convincing senior leaders in Mexico and at headquarters required clarity, confidence, and an understanding of the business beyond finance alone.That moment reflects a career shaped by early responsibility and proximity to decision-makers. From ERP implementation work—where he adapted U.S. costing systems to Mexico's 100% inflation environment—to treasury leadership, Pliego learned how finance decisions land inside real operating constraints, he tells us. Those lessons were tested again when he left P&G for Sara Lee, joining as the second employee in Mexico. Suddenly, he was learning how to import product, choose systems, hire teams, and manage risk without the safety net of a mature organization.At Diageo, that operational grounding met strategy. As CFO of Mexico, Pliego helped lead a six-month effort to craft a plan to triple the business in three years, he tells us. Finance worked alongside marketing, sales, and operations to define investments, risks, and measurements, while leaders focused on inspiring people and course-correcting quickly.Today, as CFO of Improving, Pliego carries those lessons into a faster, private-equity-backed environment. Speed matters, but discipline matters more. He's shortened the close, sharpened data visibility, and applies the same lens to AI—calling it “a very hungry monster” that only delivers value when fed consistent, high-quality data, Pliego tells us.

In his first “60 to 90 days” as CFO of Presidio, Manny Korakis learned that preparation doesn't cancel pressure, he tells us. “Now the buck stops here,” he tells us, and he “didn't really appreciate the pace” required until he was living it daily, he tells us.Korakis traces his move into enterprise thinking back to the McGraw Hill companies. Early on, he was “very technical” and “pretty close” to a singular controllership focus, he tells us. Then a mentor CFO pulled him into what they called the “growth and value plan,” he tells us. He worked on the “system landscape” and “data flow,” and on portfolio decisions about which assets were core and which were “distracting,” he tells us. That work drove the separation of McGraw Hill Education from the rest of McGraw Hill and a rebranding to “S&P Global,” he tells us. It also surfaced “hidden gems of value,” he tells us. Seeing theory turn “real life” became his “aha moment,” he tells us.In a later chapter, Korakis served as CFO of S&P Dow Jones Indices, where partners were aligned “in many cases,” but “not always aligned,” he tells us, requiring balance of “different needs and expectations,” he tells us.That arc shapes how he defines finance: not just “counting the beans,” but “highlighting the key things” so others decide better, he tells us. Today, he says finance “own[s] the model” for where Presidio wants to go, he tells us, and AI starts with “bite sized pieces,” he explains.

As one year closes and another begins, most of us are wired to look forward—to new goals, fresh plans, and the next chapter. But this special episode of CFO Thought Leader invites you to do something slightly different: look back. Not to financial milestones or career titles, but to the moments that quietly shape who we become long before anyone hands us a business card.In this episode, three CFOs take us back to the earliest chapters of their lives—stories of family, displacement, discipline, sacrifice, and unexpected kindness. You'll hear how a father's insistence on “trying,” a mother's balancing act between career and family, and a landlord's life-altering act of generosity became the invisible architecture behind leadership, resilience, and purpose. None of these moments appear on a résumé. Yet each one echoes through boardrooms, decision-making, and how these leaders show up for others.As we release this episode on New Year's Eve, it feels like the right reminder: progress isn't only measured by what we build next, but by what shaped us along the way. Before the spreadsheets, before the titles, before the outcomes—there were people, moments, and values that set everything in motion.We hope these stories give you pause, perspective, and perhaps a renewed appreciation for the beginnings that make all the difference.

When it came time to pick our holiday bonus episodes, Tim Arndt quickly came to mind. Few companies sit at the crossroads of as many 2025 storylines—tariffs, data centers, and AI—as Prologis. In our February conversation, Tim walked us through a “merger of equals” that reset leadership, the capital-markets discipline that followed, and why logistics is about “atoms, not electrons.” He tells us Prologis oversees roughly 1.3 billion square feet across 20 countries, with nearly 3% of global GDP touching its facilities. From post-GFC balance-sheet rigor to new rooftop energy and mobility plays, this one captured listeners' attention—and still feels timely. Enjoy this rerelease of one of our most-played episodes of the year.

David Den Boer traces the origins of the EPM Summit to a pattern he kept seeing across projects. “Sometimes the error is not necessarily beginning in the project,” he tells us, “but in the way they selected the product.” Too often, he observed, finance teams were locked into technology decisions before fully understanding their requirements—or their alternatives.That realization reshaped how he thought about impact. While Den Boer says he enjoys solving customer problems through implementations, he began to focus on “slower, moving bigger problems,” including gaps in thought leadership and how organizations evaluate EPM solutions in the first place. The Summit, he tells us, was designed to address that upstream decision-making moment.He draws on experience hosting EPM-focused events beginning in 2009, after SAP acquired OutlookSoft. At large vendor conferences with “hundreds of products,” he explains, it was difficult for EPM practitioners to get focused answers, connect with peers, or evaluate options objectively. As legacy platforms declined, customers increasingly asked him where to go next—and how to choose wisely.That question has only intensified with AI. Den Boer tells us finance teams are now being asked to rethink processes “from a first principles perspective.” Without that reset, he warns, organizations risk “just bolting on AI” to workflows that haven't fundamentally changed in decades.The EPM Summit reflects that conviction. Den Boer says he personally curates content to avoid “glossy marketing stuff,” relying instead on practitioners who have delivered dozens—or hundreds—of projects. Panels, hands-on product access, and difficult vendor questions are all designed to give finance leaders what they rarely get: clarity before commitment. In an era of expanding choice, the Summit is built around a simple idea—better decisions start earlier.

As the year comes to a close, we're revisiting a conversation that feels newly relevant. This week, we're re-releasing our CFO Thought Leader episode with Jonathan Carr, recorded three years ago—long before any exit was in view, but rich with insight into how he thinks about leadership, growth, and decision-making under uncertainty.That mindset was shaped early. Just 18 months after finishing college, Carr was placed in charge of a major Oracle implementation at a Stryker manufacturing plant in Puerto Rico. He had never led systems work before. The advice from his division controller was simple and direct: “find the opportunities that either get you promoted or fired,” Carr tells us.The six-month project forced him to work across manufacturing, IT, and finance to understand how transactions actually flowed through the plant. Carr describes the learning process as peeling back layers “like an onion,” where each answer revealed more complexity, he tells us. It was an early lesson in getting out of one's comfort zone and doing work before feeling fully prepared.That approach carried forward as Carr moved through FP&A, accounts receivable, and customer-facing roles, and later joined SurveyMonkey when the company was generating less than $100 million in revenue. There, he helped build finance capabilities, supported acquisitions, and participated in capital raises totaling nearly $1 billion, with less than $100 million in primary capital, Carr tells us.Later, at Atlassian, Carr was part of the finance leadership team during the company's transition from on-premise software to the cloud. The shift required conviction, transparency, and clear communication with employees and investors, even as near-term economics changed, Carr tells us.In the episode we're re-releasing today, you'll hear Carr reflect on growth, influence, and adaptability. “I reserve the right to get smarter,” he tells us—a line that neatly captures how he has approached each chapter of his career, long before the outcomes were known.

As we re-release this conversation with CFO Karen Williams during the holiday week, we're opening the episode with a short preface drawn from something she shared recently on LinkedIn. In a post about books that shaped her as a leader, Williams reflected on culture, bias, and the importance of staying open to different perspectives—ideas that echo throughout this episode and frame how she's built her career.Those themes weren't always obvious early on.Williams traces a formative lesson back to her move from a 20-person startup into Mars, where she says she “bombed at networking.” Accustomed to a small, family-style environment, she kept what she describes as a “head down, get on with it” mentality. She didn't yet understand the importance of relationships and networks, she tells us, and after a couple of years, she left.That experience reshaped how she approached her next chapter at American Express. The culture there was “very people focused, very relationship driven,” Williams tells us, but progress still came slowly at first. It took time to move from analyst to manager as she built credibility and learned how influence actually works inside large organizations. Once she reached that level, things accelerated quickly.A structural gap gave her direct exposure to a divisional CFO, who became her sponsor and helped unlock three to four subsequent roles, Williams tells us. Over fifteen years, she held roughly nine roles at American Express—calling the experience her “Harvard School of training years.”In the episode, listeners will also hear how Williams continued to stretch herself by moving out of finance into business leadership, leading strategy through disruption, and later stepping into CFO roles where unexpected challenges—like cleaning up a balance sheet—tested her early credibility.It's a conversation about learning, reflection, and how experience—especially the uncomfortable kind—shapes leadership over time.

Roy Hefer expected a quick coffee. Instead, a “30 minutes” introduction with a newly appointed Lumenis CEO stretched “more than three hours,” he tells us, as they talked through her plan to transform a flat-growth, cash-bleeding medical device company and “ultimately take it public,” he tells us.That conversation marked a shift from theory to ownership. After five years at McKinsey—based out of Tel Aviv, but spending “most of my time abroad,” he tells us—Hefer realized he was “a doer,” he tells us. He loved delivering “an amazing model” and “a very sophisticated framework,” he tells us, but not walking away before execution.At Lumenis, execution became the point. A supply-chain initiative aimed to cut costs by 30%, he tells us; the team “managed to shave, save more than 40% cost,” he tells us. As the company prepared for a NASDAQ IPO in 2014, he tells us, his CFO pulled him closer—and Hefer had what he calls an “aha moment” where he “fell in love with finance,” he tells us, seeing how finance shapes decisions across fundraising, M&A, and expansion, he tells us.Years later, after a second IPO chapter at Hippo Insurance in 2021, he tells us, Hefer chose the CFO path at Perk. There, late 2022 fundraising forced a fork: accept “highly dilutive” capital or pivot toward profitability to become “default alive,” he tells us. For Hefer, that's the job: frame options early, build trust “brick by brick,” he tells us, and let the best decision make itself.

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.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.

The moment that stayed with him began at a marketplace where sales dashboards showed 40% gross margin—yet finance closed the books at 20%, Boon tells us. The gap, he discovered, lived in the shadows: rebates, discounts, and “free” services that never touched operational metrics. He manually traced economics to the client level and found margins many considered healthy were thin—or nonexistent. One customer representing roughly 30% of revenue delivered 0% gross margin, Boon tells us.That scene explains his broader path. He started in London investment banking “working on deals 24/7,” then spent five years at McKinsey across Europe on corporate finance and strategy. At Zalando he founded Strategic Finance to ready the company for IPO—tightening the P&L and working capital. Hypergrowth taught him that unchecked hiring breeds overlap and data drift, so ownership and reporting must evolve with scale, Boon tells us.He gravitates to complexity. At his current company—public since 2021 and combined with a U.S. competitor bought for “about a billion USD”—systems sprawl and legacy platforms made accuracy difficult while two-thirds of revenue came from the U.S., across 130 countries with people in 14, Boon tells us. He cut legal entities from 28 to 14, moved to one ERP, and shortened the monthly close from “15 days” to “five or six days,” Boon tells us. Two efficiency programs, a 120 million refinancing, and a rights issue 60% oversubscribed rebuilt credibility.Back at the marketplace, he installed a pricing director reporting to finance, killed blanket rebates, and tied commissions to net revenue. Within 12 months, margin rose from 20% to 40%, Boon tells us—proof that disciplined economics, not dashboards, drive durable turnarounds.

In this special episode of CFO Thought Leader—the first of three produced in collaboration with The Suite, Shaun Sethna (General Counsel and GM for the L Suite) maps where CFOs and GCs misjudge contract risk and how to collaborate effectively. He spotlights “locked-in” deals that still enable termination via vague clauses or missing notice-and-cure. Start with strategy alignment, then cross-train—mini finance for lawyers, mini legal for CFOs—and empower teams to escalate wisely. He urges adopting AI to summarize agreements, surface obligations, and route risks. Looking ahead, he flags AI agents as SaaS “users,” which could upend seat-based pricing. He closes with an M&A example where mutual fluency let GC and CFO catch material misses.• Align strategy first; contracts follow business intent.• Cross-train teams to spot each other's risks.• Adopt AI to illuminate obligations and exposure.

When Procter & Gamble asked Atsushi Kitamura to move from finance analysis into running a manufacturing plant, he didn't hesitate. “They always give me next challenge to stretch me,” he tells us. Managing one of P&G's large diaper plants in Japan forced him to apply finance in real-time operations—a proving ground that shaped his comfort with change and appetite for transformation.That readiness carried him from consumer goods to logistics, restaurants, and electronics before arriving at Astellas Pharma, where the stakes are now measured in science and strategy. When he joined in 2023, Astellas had just completed a $6 billion acquisition that shifted it from a net-cash to a net-debt position. Hired to “put financial disciplines and make the balance sheet stronger,” Kitamura tells us he views the moment as a “transformative timing” for the company. Loss of exclusivity on a prostate-cancer drug representing “more than 40 percent of our revenues” demands reinvention.His three-part playbook focuses on growing core brands, investing in science creation, and executing what he calls “sustainable margin transformations.” The approach has begun to pay off—“top line 19 percent, profit 40 percent,” he tells us—signaling a finance organization in renewal.Now he's turning to technology to sustain that momentum. Describing the shift from RPA to “agentic AI,” Kitamura explains, “I just ask agent AI to do that booking.” He calls it a tipping point that will “change significantly the way how we work.”Still, he adds, leadership begins with listening. “Don't pretend I know everything,” he tells us. For Kitamura, finance transformation starts not with machines or metrics—but with humility.

On a quiet afternoon in Punta Cana, Michael Levine sat alone on a stretch of white sand. The turquoise water and silence offered the perfect scene for rest—until he realized what was missing. “I didn't have my phone and I didn't have my laptop,” he tells us. “That's what makes me happy… I love doing work from the beach.” It was there, after stepping down as Payoneer's CFO, that Levine accepted a truth about himself: he wasn't ready to retire.Levine had spent 11 and a half years helping Payoneer scale from about 100 employees to 3,000 and from $150 million to more than $80 billion in annual volume. He guided the company from private to public in June 2021 and from unregulated to regulated operations. When he left in 2023, he planned a pause but instead found himself drawn to a new frontier.Calls from crypto companies arrived during what he calls the “crypto winter.” Although he had once avoided digital assets entirely, he became fascinated by “decentralized finance,” “smart contracts,” and the tokenization of real-world assets. A meeting arranged by Spencer Stuart with the CEO of Fireblocks solidified his next move. “When you don't know which horse to pick in a race,” Levine tells us, “buy the racetrack.”Fireblocks, he explains, is the infrastructure that secures digital assets for enterprises through self-custody and cyber-grade protection. For Levine, it was a chance to apply a career's worth of scaling and governance experience to a technology poised to define the next decade of finance.

She starts with tape from the field, not the spreadsheet. Listening to enterprise sales calls, Amy Foo heard customers whose usage rose and fell with seasons. Fixed per-seat pricing “wasn't quite hitting the mark,” she tells us, so she piloted a pooled-seat model that flexed monthly within an annual commitment—turning smaller clips into “one to five million” deals and lifting revenue “six to seven times per customer,” she tells us.That instinct—to meet the customer where they are—threads through her journey. Early at Zendesk, she was “employee number one in the region,” handling FP&A, accounting, taxes, and team-building as the business scaled, she tells us. Trust won her a dual path: SVP of Global Finance Operations (deal desk, billings, shared services) and APAC managing director, aligning teams across seven countries, she tells us. Mentors' unvarnished feedback helped her shed imposter syndrome and lead without geographic ceilings.Today at Ignition, she reduces complexity to a few levers—ARR, payments volume, cash flow—and aligns accordingly, she tells us. She monitors top-of-funnel quality and pipeline coverage daily to steer marketing spend and sales motions, she tells us. On pricing, she watches what customers pay and repackages value by segment, she tells us. She leads with customer insight, she tells us.As for AI, she calls it “not a magic pill,” advocating first for AI built into existing vendors, then new tools where capabilities are missing, she tells us. Finance, after all, is “about narrative and conviction”—numbers that move people to act, she tells us.

When Joe Custer describes Intrado's purpose, he begins with a story that traces back almost half a century. The company, he tells us, was born inside the Boulder County Sheriff's Department when someone asked whether there might be a better way to connect a caller in distress with a first responder. “Turns out they were on to something,” he adds. Today that idea has scaled into a mission-critical network touching roughly 90 percent of all 911 requests for assistance.Custer explains that Intrado “has to operate like a utility … we cannot fail.” Reliability is not a metric to be met but a promise to the public, one he refers to as “public safety grade.” Behind that standard lies a web of acquisitions—eight to ten over time—that were never fully integrated. That challenge, he says, became opportunity when Stonepeak Infrastructure Partners carved Intrado out of West Corporation and began investing to harden its network and modernize its operations.As both CFO and SVP of Operations, Custer leads a transformation aimed at restoring Intrado's position as the thought leader in emergency communications. The work goes beyond financial engineering; it's about aligning systems, culture, and purpose around a single mission: saving lives. “We want to be the most trusted authority in public safety,” Custer tells us, describing a workforce “deeply committed to the cause.” In his view, reliability, investment, and mission are inseparable—the essential framework for Intrado's next 50 years.

On his first day in investment banking, Clayton Kossl was “thrown right into the cauldron.” With few senior professionals in the small aerospace and defense group, junior bankers like him were expected to face company owners directly. “You had to understand the businesses inside and out,” he tells us. The experience forced him to blend analytical depth with the interpersonal agility needed to earn trust in every room.That mix of skills—numbers and nuance—became a through line in Kossl's career. At ZocDoc, he joined a Strategic Finance team that partnered closely with the CEO and CFO, taking ownership of decisions that rippled across the fast-growing health-tech firm. The role taught him that financial modeling and relationship-building could coexist—and that influence often came from understanding how leaders think, not just how spreadsheets add up.Later, when Kossl joined Paintzen as one of roughly a dozen employees, those lessons proved vital. He rebuilt systems from scratch, partnered daily with the CEO and COO, and touched nearly every function of the business. “Someone had to do it,” he recalls. His ability to translate operational chaos into financial clarity helped guide Paintzen through its expansion and eventual sale to PPG Industries.Across these chapters, Kossl's story reveals a consistent pattern: using strategy to tell better stories. Whether advising founders or steering finance in ad-tech today, he views storytelling not as spin, but as structure—the way finance can make complexity understandable and transformation achievable.

“InvoiceCloud is not just payments,” Chris Sands tells us. Sitting inside the company's finance organization, he sees a platform built to change habits—helping businesses shift customers from paper invoices and mailed checks to fully digital transactions. The success metric, he adds, is simple: “Do more of their customers stop receiving paper invoices, stop mailing in checks, and do both of those things digitally?”That clear yardstick reflects how Sands thinks about growth. He describes a foundation rooted in existing customers even as the broader economy accelerates toward digital payment adoption. Utilities and insurers remain core markets, yet new verticals, such as consumer finance, beckon. Each expansion, he notes, must rest on data that confirms user behavior is truly changing.Inside finance, Sands has built what he calls a Strategic Finance function to mirror that discipline. The group handles special projects and, increasingly, AI initiatives—efforts he says once fell entirely within FP&A. Now they stand on their own “leg of the stool,” amplifying how finance supports innovation.That mindset extends beyond the department. Sands helped stand up an AI Ops team—an internal SWAT group that guides employees exploring AI tools. Instead of experimenting in isolation, staff can bring use cases to the team for help. For Sands, finance's role is to stay analytical amid the excitement: “We can add more value … by helping the rest of the org with [AI] and using our finance skill set to understand where the best opportunities to create business value exist.”

In this episode of Planning Aces, host Jack Sweeney and resident thought leader Brett Knowles explore how finance leaders are approaching AI's early returns—balancing efficiency, experimentation, and human judgment. CFO Craig Foster of Pax8 discusses how AI enablement is driving measurable productivity gains. CFO David Obstler of Datadog reflects on finding ROI amid rapid innovation and market demand. And CFO Ben Gammell of Brex shares why forecasting still requires human intuition despite data-driven progress. Together, their insights reveal a spectrum of FP&A strategies defining the modern CFO's mindset toward AI adoption and business transformation.Brett Knowles' Key TakeawaysBrett Knowles observes that finance leaders are positioning themselves along a broad continuum—from bold experimentation to cautious skepticism—when it comes to AI in planning. He notes a shift in tone: CFOs are now openly discussing productivity gains and cost efficiency rather than avoiding them. Knowles cautions against overreliance on ROI metrics, emphasizing instead disciplined cost management, pragmatic experimentation, and the evolving role of finance in navigating technology-driven transformation.

When Kimberlee Duval arrived at Cymbiotika, the wellness company was preparing a leap few bootstrapped brands attempt—moving from direct-to-consumer to retail shelves. “Our two owners, Charlene and Shahab, have done everything direct,” she tells us. “They wanted to build an organization for the long term.” That resolve led the company to take on debt rather than private-equity money to fund its Sprouts launch in 2024. The risk paid off: Sprouts highlighted Cymbiotika's success in its quarterly earnings release, proof that intentional growth can outperform speed.Now, with products heading to 1,988 Target stores, Duval's finance team is focused on scaling without losing clarity. “We restructured the finance function to align with that growth strategy,” she tells us, pointing to centralized operations in NetSuite, expanded FP&A and cost accounting capabilities, and the creation of clear SOPs. Technology, she believes, is the enabler that keeps teams lean and insights sharp.“There's no reason to segregate between the groups,” she explains, describing her cross-channel approach to e-commerce and retail finance. AI tools and automated workflows now handle much of the transactional load, freeing her people to focus on analysis and collaboration.At the heart of her leadership philosophy is unity. “We're a team … with a common purpose and a common goal,” Duval tells us. That ethos—pairing disciplined systems with shared intent—continues to shape Cymbiotika's transformation from a digital wellness brand into a multichannel movement for intentional living.

When Steve Sutter joined Celigo five years ago, he stepped into a company positioned not as another SaaS app but as what he calls “the infrastructure, the piping, the plumbing” of business automation. Celigo, he tells us, moves data between systems like Salesforce, NetSuite, and Snowflake so companies can “create very sophisticated business processes” without the friction of disconnected silos.For Sutter, the real work of finance begins behind that plumbing. “As CFO, you have to build a sustainable business model,” he tells us, one rooted in clear unit economics—how each dollar of new recurring revenue is earned and what it costs to deliver value. That analytical discipline, he explains, gives finance a vantage point “no one else has,” allowing it to balance engineering ambition with go-to-market execution.Working inside a privately held, fast-growth environment, Sutter views resource allocation as both art and accountability. Sometimes, he says, companies must “invest in sales and marketing at an excessive rate” to gain traction—but the test is whether the model still makes mathematical sense. He partners closely with the CRO and CMO to watch metrics like the quota-to-OTE ratio and pipeline efficiency, adjusting as conditions change.Even at scale, Sutter keeps a simple mantra: acknowledge failure quickly. “As soon as you've acknowledged failure,” he tells us, “you can move on to something that will likely be successful.” It's a principle that keeps Celigo's growth disciplined—and its automation ambitions grounded in financial logic.

In 2008, Beth Gaspich stood on the floor of the New York Stock Exchange, ringing the bell as RiskMetrics went public. What made the moment extraordinary was its timing—amid one of the most volatile markets in decades. The IPO decision, she tells us, came “down to the wire.” After months of preparing the S-1, long roadshows, and weekend work with auditors, leadership had to choose: delay indefinitely or seize a fleeting opening. They chose action, and the listing became a defining milestone in her career.That experience shaped her conviction that preparation and clear communication are indispensable when markets are uncertain. It also foreshadowed the way she would later lead NICE through its own transformation. When she became CFO in 2016, NICE was largely an on-premise software company with roughly $1 billion in revenue. Today, she tells us, the firm is approaching $3 billion, with $2.2 billion in cloud revenue. “We don't put boxes around people,” she notes, describing a culture where finance leaders are expected to help drive strategy, not just report results.Her approach to AI investment echoes that belief. She explains that NICE's AI and self-service ARR reached $238 million, growing 42% year-over-year. Rather than measure ROI only through headcount reduction, she emphasizes redeploying people to more strategic work. Internally, AI “champions” in each function track outcomes with KPIs. From ringing the NYSE bell to scaling a global AI platform, Gaspich's journey illustrates how finance leaders can balance precision with boldness when transformation is on the line.

When David Obstler joined Datadog in 2018, the company's co-founders had already built momentum with a product that observed modern cloud workloads. What struck Obstler was the alignment with a powerful long-term trend—the shift from legacy, on-premise systems to modern cloud applications. “It was a product that had a lot of product market fit in a really strong growing market,” he tells us.From that foundation, Datadog scaled rapidly. Today, the platform serves more than 3,100 customers worldwide, including Samsung, Nasdaq, Shell, Autodesk, and Toyota. The company recently entered the S&P 500 after reporting more than $820 million in second-quarter revenue—a 28% year-over-year increase—alongside $200 million in free cash flow, Obstler tells us.The CFO attributes the growth to Datadog's unwavering commitment to product-led innovation. The company began in infrastructure monitoring and quickly expanded into logs, application monitoring, and security. “The company invests R&D at very high and consistent levels to continue to maintain and grow the platform,” Obstler tells us.His own role centers on scaling the infrastructure needed to support expansion. That includes building global go-to-market operations and strengthening his team across financial planning, predictability, and business operations. “We've been investing behind this growth opportunity and doing it in a strong, prioritized way,” he tells us.With new investments in AI, Datadog is preparing for its next chapter. For Obstler, disciplined prioritization and product-driven growth remain at the heart of how finance can fuel scale.

On her first day as CFO of UHY, Laura LaPeer asked a simple question: “Do you guys do Copilot?” She had grown accustomed to using Microsoft's AI assistant for tasks ranging from summarizing documents to creating slides, and she wanted it in place immediately. The request, she tells us, reflected both her pragmatism and her view that technology should be leveraged quickly, but carefully, to support higher-value work.That same instinct—to look beyond the surface of a task—has shaped her career. At an earlier company, LaPeer noticed that procurement and treasury were being handled transactionally. Purchase orders were checked for compliance, and cash was managed cyclically. By zooming out, she recognized the chance to turn these into strategic functions: evaluating vendor risks, aligning relationships with business goals, and putting idle cash to work. This shift, she tells us, allowed finance to deliver tangible impact.Her time at ProQuest, where she witnessed growth through M&A, gave her a business lens she later carried into her CFO role at Plante Moran. Now at UHY, she applies the same perspective. With Summit Partners as a new investor, the firm is targeting $1 billion in revenue within five years, LaPeer tells us. Growth will come through both acquisitions and services such as outsourced accounting, valuation, and state and local tax.To get there, she emphasizes unity. “One UHY,” she says, requires integrating regional groups, building the bench, and ensuring technology like Workday delivers consistent, firm-wide insights.