CFO THOUGHT LEADER

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.