CFO THOUGHT LEADER

Tom DiDesidero describes a period when SmartRecruiters was actively taking customers from a much larger competitor. It wasn’t just momentum—it was proof. “We were stealing a lot of their customers,” DiDesidero tells us, describing how that traction became a defining signal of value.At the same time, SmartRecruiters was moving quickly on a new front. “We were really the first mover in the embedded AI product,” DiDesidero tells us, emphasizing that speed and execution—not perfection—mattered most. The team brought its AI platform to market early, leaning on strong customer relationships and credibility. Beta users quickly became paying customers, reinforcing that the strategy was working.This combination—customer momentum and early AI execution—positioned SmartRecruiters as more than just a product. It became a strategic asset. “It’s important… it’s not just the theory, it’s the execution,” DiDesidero tells us. That distinction ultimately shaped how SAP evaluated the opportunity.Still, the deal itself was only the beginning. Integration, he explains, is where value is realized. “You keep being you. Don’t let our bureaucracy slow you down,” DiDesidero tells us, recalling the message from SAP leadership.Six months in, the reality is nuanced. “It’s a mixture of progress and pain every day,” he tells us. Yet, for DiDesidero, the differentiator remains the people—teams committed to building, adapting, and pushing forward.In his view, success at scale isn’t just about strategy or technology—it’s about sustaining the behaviors that made growth possible in the first place.

Within his first 90 days at Docusign, Blake Grayson recognized the company needed to make difficult efficiency decisions following a post-COVID slowdown. Acting quickly, he partnered with leadership to address the issue, noting that “making the hard decision faster is way better than waiting,” Grayson tells us. That moment set the tone for how he approaches finance leadership—decisive, data-driven, and focused on forward momentum.That same mindset now shapes how he views Docusign’s evolution. Long known as the “default eSignature business,” Grayson tells us, the company serves over 1.8 million customers worldwide. Yet he emphasizes that the real opportunity lies beyond the signature itself. “There’s so much more to an agreement than just the act of the signature,” he tells us, pointing to missed renewal clauses and buried pricing terms as examples of untapped value.This realization underpins Docusign’s push into intelligent agreement management. Early results suggest traction: the platform reached more than $350 million in annualized recurring revenue within 18 months, Grayson tells us, contributing to a broader milestone of over $1 billion in both billings and free cash flow. Still, he remains measured, describing the progress as “early validation” while acknowledging the company is “in the early innings,” he tells us.Across these moments, a consistent theme emerges. Whether evaluating operational efficiency or unlocking customer value, Grayson’s approach centers on acting with clarity and speed—using finance not as a constraint, but as a catalyst for disciplined growth.

Late one night in Calgary, Amy Wang was running final checks on a billion-dollar transaction when something didn’t sit right. “My immediate instinct…was to dismiss it,” she tells us. After all, multiple teams and advisors had already vetted the deal. But she couldn’t let it go. Instead, she challenged the work—carefully, respectfully—and was right. The correction prevented more than a million dollars from being misallocated.That moment became a defining inflection point. It reshaped how Wang viewed leadership—not as deference to expertise, but as the willingness to trust one’s own judgment. Titles and credentials, she tells us, may signal experience, but they don’t guarantee accuracy.Her path to CFO may appear traditional—beginning in audit and progressing through finance roles—but Wang emphasizes that the real education came from moments like this. Early in her career, she believed success meant mastering the numbers. But during Solium’s acquisition by Morgan Stanley, she saw that “everyone can read a spreadsheet,” she tells us. What truly moved the deal forward was the ability to articulate a compelling narrative behind those numbers.Today, as CFO, Wang carries both lessons forward. Technical skills may “get you into the room,” she tells us, but leadership requires asking better questions, making decisions with imperfect information, and having the courage to speak up.In an era increasingly shaped by AI, she believes that judgment—not data alone—will ultimately differentiate finance leaders.

In 2023, stepping into the CFO role at Twilio, Aidan Viggiano faced a defining reality: “the first hard call was a layoff,” she tells us. The company had surged during the pandemic as digital communications accelerated, but by mid-2022, growth slowed while profitability lagged. “We can’t be slowing in growth and not be profitable and not generating cash,” she explains, describing the moment that forced a fundamental shift in strategy.Over the next six months, Twilio reduced its workforce by about 40%, she tells us—a decision that tested not just financial discipline but leadership resolve. For Viggiano, the experience underscored a core principle: communication is as critical as the decision itself. “The importance of over communication…being transparent… and treating everybody with humanity,” she tells us, became central to how she navigated the transition.This moment reflects a broader leadership mindset shaped by aligning growth with accountability. The pivot from rapid expansion to balanced performance required not only cost action but a cultural reset—one grounded in clarity, trust, and execution.At the same time, Viggiano continues to frame Twilio’s value through its role as a communications infrastructure provider, powering interactions between businesses and consumers at scale. From authentication codes to real-time customer engagement, the company’s reach is often invisible but essential.For Viggiano, the lesson is clear: finance leadership is not only about numbers—it is about guiding organizations through inflection points with transparency, discipline, and humanity.

Early in his career, Rich Schmidt recalls presenting an analysis of an operational challenge to leadership—only to be told, “we want you to go fix it.” The assignment marked a turning point. What began as financial analysis quickly became ownership, execution, and accountability across the business.That moment would come to define Schmidt’s future career path—one that would unfold almost entirely within Inmar Intelligence. After starting in public accounting—“a grind,” as he tells us—he gained exposure to multiple industries in rapid succession, from manufacturing to healthcare. Yet it was inside Inmar where his trajectory took shape, as he moved beyond traditional finance into roles that blended technology, operations, and execution.Rather than follow a conventional path across multiple companies, Schmidt built a reputation as a problem solver within one. Each new challenge expanded his scope. Each solution deepened trust. Over time, that pattern—analyze, act, deliver—created opportunities that no job change could have replicated.At times, the path brought uncertainty. He admits he wrestled with whether he was moving “sideways” instead of forward. But those lateral moves became his advantage—preparing him to lead initiatives like M&A integrations and enterprise transformations that required both insight and execution.Years later, that same mindset informed a defining leadership decision. Facing operational complexity after multiple acquisitions, Schmidt led a transition to a cloud-based ERP system—an investment that reduced the company’s close cycle from “eight to ten days” to “four and a half days,” he tells us.Looking back, Schmidt’s journey challenges a common assumption: that advancement requires moving on. In his case, growth came from going deeper—solving problems across the enterprise and building a reputation that ultimately carried him to the CFO seat.

Tony MacDonald prefers a different image of the CFO role—one that replaces restraint with direction. “I would like to be considered as one of the people on the stagecoach that helps hold the reins,” he tells us, describing sales as “the horses that I want galloping always full speed ahead.”That mindset was shaped during his time at Oracle, where he operated inside a deeply sales-driven organization. There, MacDonald learned that finance could influence growth not by limiting it, but by guiding it. His role extended beyond oversight—he led financial planning across an organization of roughly 140,000 people, gaining visibility into how revenue engines scale and where they break down, he tells us.Today, that experience informs how he approaches revenue operations. Rather than acting as a gatekeeper, MacDonald positions finance as an enabler—rewarding “exceptional performance…unconditionally relative to quality revenue,” while maintaining rigorous control over the metrics that matter, he tells us.This balance requires precision. From lead generation through the sales funnel, MacDonald emphasizes continuous calibration—using data to refine performance and ensure that growth is both measurable and repeatable. He remains actively involved, even helping build marketing dashboards to improve visibility across the funnel, he tells us.For MacDonald, revenue operations is not a support function—it is where finance and strategy intersect. The goal is simple: let sales run fast, but make sure they’re headed in the right direction.

In this CFO Thought Leader episode, Jack Sweeney speaks with technology general counsel Akin Adekeye about when AI becomes a board-level concern. Adekeye explains AI crosses into governance when it impacts risk, capital allocation, and competitiveness. He highlights “shadow AI” risks, regulatory uncertainty, and the need for structured oversight. Effective governance includes board involvement, executive ownership, and clear operating controls. CFOs play a central role in balancing innovation with risk, ensuring organizations neither lag competitors nor expose themselves to harm. Looking ahead, AI governance will become standardized, with rising expectations for board literacy, disclosure, and formal control frameworks.Three Key Takeaways1. AI becomes a board issue when it impacts enterprise risk and capital allocationThe transition point is not technical maturity—it’s strategic exposure. Once AI influences risk posture, investment decisions, or long-term strategy, it moves beyond IT into board-level oversight.2. Governance must evolve alongside AI adoptionBoards can no longer treat AI as a siloed innovation effort. It requires structured governance frameworks that address accountability, transparency, and cross-functional implications.3. Legal and finance leaders play a critical translation roleGeneral Counsels and CFOs are essential in helping boards understand AI’s implications—bridging technical capabilities with risk, compliance, and strategic decision-making.

Marc Mehlman still recalls the moment a senior leader pulled him aside and told him he was “in such a rush” and needed to “enjoy the journey,” he tells us. At the time, Mehlman was part of a leadership program filled with high achievers eager to move quickly into senior roles. Instead, he took a different path—spending nearly a decade moving laterally across FP&A, corporate development, strategy, and operational roles.That deliberate detour became the foundation of his leadership philosophy. By working across divisions and even geographies, Mehlman built a broad understanding of how businesses actually function. Later, when he stepped into operating roles—including leading a roughly $1 billion revenue segment—he began to see a gap. Many finance leaders could explain results, but not the decisions behind them. “They’re just numbers,” he tells us, emphasizing that financial outcomes are simply the result of actions taken across the business.Another pivotal moment came when he initially declined an investor relations role. After multiple conversations with senior leadership, he accepted—and discovered the power of communication. There, he learned to tell a consistent story, build credibility, and deliver on expectations quarter after quarter.Today, as CFO, those experiences converge. His early focus on exploration, combined with operational insight and storytelling discipline, shapes how he evaluates decisions, partners across functions, and defines the modern CFO—not as a reporter of results, but as an architect of them.

Michael Perica had been discussing the market implications of AI with investors for a number of years, but the market didn’t fully react—until one particular moment. In late January and early February, a wave of announcements around enterprise-focused AI models and workflow plugins triggered what has become widely known as the “SaaS-pocalypse.” In a single day, roughly $258 billion in SaaS market value disappeared, he tells us.For Perica, the episode confirmed something he had already been sensing in conversations with investors and clients. The traditional path to enterprise modernization—committing to large, monolithic software platforms—was no longer the only option. AI, particularly emerging agentic AI technologies, was beginning to offer organizations a new route: modernizing workflows and processes without necessarily replacing entire systems.The sudden market reaction accelerated those conversations. Investors and executives began reaching out to Rimini Street asking whether this moment validated the alternative technology path the company had been discussing. For Perica, the answer was clear. The event underscored that organizations now had the ability to tailor AI models directly to specific business processes rather than conforming their operations to a rigid software roadmap.That shift has shaped how Perica thinks about strategy going forward. Instead of viewing AI purely as a tool for efficiency, he sees it as a catalyst for enterprise-wide transformation. Finance leaders, he argues, now have an opportunity to work closely with CIOs to rethink workflows, eliminate operational bottlenecks, and deploy targeted AI solutions that create quick wins across the organization.In Perica’s view, the SaaS-pocalypse wasn’t just a market correction. It was a signal that a new technology paradigm had arrived—and that forward-looking CFOs must be ready to lead the change.

Andrew Bender still remembers a moment from high school football practice when a coach challenged him with a simple question: “Do you want to be all conference or all state?” The comment surprised him. At the time, Bender tells us he wasn’t even sure he had the potential to reach the lower bar. Yet the moment stayed with him because it revealed something important—that sometimes others see possibilities before we do.That lesson about recognizing potential shaped how Bender approached his career decisions. Early on, while working at William Blair, he faced a choice common among his peers: continue toward private equity or pursue a different path. Instead of following the typical investment track, he realized he preferred working inside organizations rather than advising them from the outside. The parts of investment banking he enjoyed most involved “diving into the organizations” he represented, Bender tells us.Over time, that realization led him toward roles blending strategy and finance. Consulting and business school helped him develop structured problem-solving skills and the ability to learn new industries quickly. Later, at Snyder’s-Lance, he worked across corporate strategy and business-unit finance, gaining operational perspective that would prepare him for future CFO roles.That blend of strategy and finance thinking surfaced again after Bender joined BNI Global. Preparing board materials, he realized the company tracked numerous KPIs but struggled to explain performance drivers. If the metrics didn’t link to financial outcomes, he recalls thinking, “what are we doing here?”The solution was simplification. Bender helped refocus leadership on five core business drivers—member renewals, visitor activity, conversion rates, chapter launches, and pricing—while teaching operational leaders how those metrics translate into financial performance.

Early in Lucanet’s expansion, two Chinese employees working in Germany had a moment of insight. Seeing how configurable the consolidation software was, they believed it could succeed in their home market. Acting on that conviction, they traveled from Berlin back to China and built what would become Lucanet’s Chinese business. The story illustrates how a tool designed for global complexity could travel easily across borders, Gurney tells us.Lucanet’s origins are firmly rooted in Germany, where the company first built its reputation with a consolidation platform designed for companies operating across multiple jurisdictions. That design decision proved foundational. Because customers often consolidate entities across countries, the platform had to integrate financial data from different jurisdictions and support multiple accounting frameworks, Gurney tells us. The system can report under German GAAP, IFRS, or different management accounting rules and allows users to toggle between those views efficiently, he tells us.Read MoreToday, the company’s geographic reach reflects that original cross-border orientation. While Germany remains Lucanet’s strongest market, the company now operates across Europe and Asia, including the Netherlands, Switzerland, France, Italy, Spain, the United Kingdom, China, and Singapore, Gurney tells us. Increasingly, a majority of new customer bookings come from outside Lucanet’s historical DACH and Netherlands markets, he tells us.Growth has also been shaped by capital structure changes. After roughly eighteen years as a founder-run business, HG Capital made a majority investment in 2022, accelerating both product development and geographic expansion, Gurney tells us.For Gurney, who joined Lucanet at the start of May last year, the company’s focus remains clear: build tools that make the Office of the CFO more effective across borders and systems, he tells us.

Ashley Still, Executive Vice President and General Manager of Intuit’s mid-market business, discusses how the expectations of finance leaders are shifting as AI reshapes the finance function. She explains how Intuit is expanding beyond its small-business roots with Intuit Enterprise Suite, designed to serve growing mid-market organizations seeking faster implementation and lower total cost than traditional ERP systems. Still highlights how AI-powered agents are helping finance teams reduce manual work, accelerate month-end insights, and focus more on strategic decision-making. As the CFO role evolves from scorekeeper to growth driver, she believes technology will increasingly enable finance leaders to connect data, manage risk, and guide business growth.

Early in his career, Intekhab Nazeer found himself sitting in go-to-market meetings rather than finance reviews. A CFO mentor had pushed him beyond traditional accounting responsibilities, exposing him to pipeline discussions and sales forecasting. That experience changed how he viewed finance leadership. Instead of simply reporting financial results, he began understanding “how pipeline is generated, how deal flow is measured, how the forecasting really works,” Nazeer tells us. The exposure reshaped his perspective, shifting his mindset from reporting outcomes to influencing them.The shift became even more real when he stepped into an interim CFO role after his mentor moved on. Responsibility changed overnight. “I was no longer supporting decisions. I was making decisions,” Nazeer tells us, describing board meetings, capital allocation choices, and the balancing act between growth and risk.Throughout his career, he continued to place finance alongside operations rather than apart from them. At one venture-backed company, that mindset proved critical. Revenue targets were being met, yet something felt wrong. When Nazeer overlaid unit economics—customer acquisition cost, payback period, and expansion revenue—he discovered the company was optimizing growth while quietly locking in unprofitable customer behavior, he tells us.The response required collaboration rather than spreadsheets alone. He worked with sales and product leaders to redefine the ideal customer profile, adjust pricing discipline, and elevate metrics like payback period and the “magic number” into core operating indicators, he tells us.The experience reinforced a lesson he carries today: the CFO role is “far less about spreadsheets and more about psychology,” Nazeer tells us. Precision creates accuracy, but influence creates outcomes.

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, hosts Jack Sweeney and Glenn Hopper lead a focused discussion spotlighting the thinking of CFO Kevin Rubin of Zscaler, CFO Bruce Schuman of Universal Technical Institute, and CFO Razzak Jallow of FloQast on how disciplined FP&A leadership is shaping AI adoption. Rubin frames AI as a capital allocation decision, supported by centralized governance to prevent tool sprawl. Schuman underscores 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.As resident thought leader, Glenn Hopper reinforces a unifying insight: AI should function as an “exoskeleton” for finance—amplifying sound processes, not replacing them. Together, Jack and Glenn connect the perspectives, highlighting a shared conclusion: AI success in FP&A depends less on speed and more on governance, architecture, and trust embedded 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 “Elia” 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.