1177: Navigating an Acquisition at the Edge of Change | Tom DiDesidero, CFO, SmartRecruiters

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.