It was a puzzle that John Wilson simply couldn’t resist. Intel had long sold processors to the federal government on a commercial basis, but the rising importance of High Performance Computing (HPC) demanded a new approach. Undeterred by the maze of federal acquisition regulations, Wilson volunteered to stand up a dedicated government unit, a move that he tells us helped unlock cutting-edge HPC research. The work took him to the edges of “bleeding-edge technology,” even if it also meant navigating the detailed rigors of government compliance.

That knack for transformation would serve Wilson well when he later encountered another pivotal moment: the day the moving truck arrived at his new home in Oregon—just as Intel announced the dissolution of the very business group he was joining. Rather than panic, he thrived, moving on to master complex FP&A and business development roles. It was the same mindset that guided him in standing up an entirely separate legal entity to better serve government contracts, broadening his view of finance from purely operational tasks to strategic decision-making.

Today, as CFO of Sabey Data Centers, Wilson continues to fuse vision with pragmatism. He has drawn from his HPC experience—where technology evolves at breakneck speeds—to guide Sabey’s approach to data center design and expansion. Collaborating with teams to manage billion-dollar investments, he remains resolute on two fronts: balancing the need for innovation with disciplined capital allocation, and preserving a culture of “good stewardship” that ensures long-term stability for tenants ranging from tech giants to smaller enterprises.

It was a phone call Amy Butte tells us she will never forget. Lifting the receiver, she heard the familiar voice of her father—an accountant who had always championed her career. But this time, his words were tinged with a curious mixture of praise and amazement. He simply couldn’t fathom how his daughter, who had taken only one accounting class, was now the CFO of the New York Stock Exchange. “Finance leadership is more than numbers,” Butte reminds us, explaining that, for her, success hinges on weaving data into a strategic narrative that shapes decisions.

That same flair for bold moves followed her into a pivotal meeting with the NYSE’s new leadership. “How’d you like to be the CFO?” she was asked on the spot, an offer so direct it felt surreal. Butte tells us she immediately saw an opportunity to modernize a centuries-old institution, and within two and a half years—half the time originally planned—she was leading the organization’s transition to a public company. The accelerated timeline tested her agility, forcing her to rethink legacy processes and overhaul entrenched systems. Through it all, she discovered that being an agent of change meant continuously blending operational discipline with forward-thinking ideas.

In this episode of Controllers Classified, Erik Zhou sits down with Karen Wu, the Chief Accounting Officer at Clari, to discuss the role of accounting in a company’s exit strategy. The conversation starts with an overview of Karen’s time in Transaction Services at PWC, where she helped a myriad of companies prepare for IPO - including Alibaba, the largest IPO in US history. Drawing on those experiences, Karen covers the reasons why a company may look for an exit, the types of exit strategies, and the role of the accounting team in those strategies.

Specifically, Karen speaks to some ‘musts’ that accounting teams have to get right no matter the exit strategy - things like closing the books on time, ensuring precision and reliability in financial statements, and being able to comply with public company requirements. She speaks to the IPO readiness timeline, and how companies should approach it not just through the lens of accounting and finance, but across all functions.

The conversation then pivots to Karen’s time at Clari. She shares her priorities as well as her POV on global accounting processes given the company’s international operations. Her number one piece of advice? Don’t be hesitant to outsource pieces of work to consultants who may have a better handle on local tax policies.

Ashim Gupta, who has evolved from a pre-IPO CFO to now serving as both CFO and COO, is busy redefining the role of finance in driving growth and innovation. Initially focused on strict financial discipline, Gupta’s responsibilities have expanded to integrate long-term growth initiatives with day-to-day operational execution.

In our discussion, Gupta explains that funding AI projects at UiPath is guided by a rigorous evaluation framework. “We assess every project based on scalability, efficiency, revenue impact, and strategic differentiation,” he tells us. This disciplined approach ensures that each AI investment not only delivers measurable ROI but also aligns with UiPath’s broader vision of merging AI with automation.

Transparent communication with the investment community has been key to this evolution. Gupta emphasizes that clearly articulating milestones and performance metrics is essential as the company’s narrative shifts from its RPA origins to becoming a leader in AI-driven automation, he tells us. This transparency builds trust and demonstrates the strategic value behind each investment decision.

Moreover, Gupta’s dual role enables him to balance aggressive AI R&D investments with the demands of core operational priorities. By bridging finance and operations, he ensures that strategic initiatives are effectively executed while maintaining robust financial discipline. As UiPath continues to push the boundaries of automation, Ashim Gupta’s strategic mindset remains central to its sustained success and innovation in the evolving digital landscape.

Like many seasoned finance executives, Damon Fletcher saw Snowflake as a game-changer in cloud-based data management. While a senior finance executive at Tableau, he championed its adoption, recognizing its ability to scale analytics and streamline enterprise data operations. But he also discovered a challenge familiar to many finance leaders—the hidden costs that come with cloud consumption-based pricing.

At Tableau, Fletcher tells us, the company’s Snowflake costs grew exponentially, mirroring a broader trend in tech where companies struggle to control cloud spend. This realization led Fletcher beyond the CFO office. In 2023, he co-founded Caliper, a company dedicated to bringing greater cost transparency and AI-powered efficiency to cloud spending.

Fletcher tells us that AI is central to Caliper’s approach. The platform leverages machine learning forecasting to predict cloud usage trends and generative AI to surface actionable cost-saving recommendations. Unlike traditional cloud cost tools, Caliper provides deep insights across Snowflake, AWS, and Datadog, allowing finance and DevOps teams to pinpoint inefficiencies in real time.

Early in his career, Lior Maza chose to immerse himself in smaller, venture-backed startups instead of large enterprises—a move that exposed him to an array of responsibilities, from fundraising, recruiting to crisis management. “When you’re in a small team,” Maza tells us, “you end up doing everything, and that’s where the agility mindset really takes root.”

Years later, after honing his skills in larger organizations, he joined Priority Software, an established yet agile cloud ERP firm. Under his guidance, the finance function embraced new performance measurements—focusing on recurring revenue, net retention, and churn—to manage a transition from traditional licensing to a SaaS model. “Agile finance leadership,” Maza tells us, “is about looking beyond immediate metrics and creating frameworks that drive long-term value.”

Bill Korn approaches board leadership with the same strategic, forward-thinking mindset that defined his CFO career. He believes a board member's role extends beyond governance to actively supporting company growth, shaping financial discipline, and guiding leadership teams through inflection points. Bill prioritizes long-term value creation over short-term gains, leveraging his M&A expertise, IPO experience, and global operations knowledge to help companies outmaneuver larger competitors. He advocates for hiring and retaining top talent, using technology as a competitive advantage, and fostering a culture of transparency and accountability—ensuring that businesses not only grow but sustain their success in evolving market conditions.

In this episode of Controllers Classified, host Erik Zhou sits down with Jeff Arensman, Controller at Bloomerang, to cover two important topics: building a finance function from scratch and the role of finance in acquisitions.

For Jeff, the two are inextricably linked at Bloomerang. As the first finance hire at the company, his first task was supporting an acquisition that needed to close in just three weeks. He then quickly turned to building a strong foundation for the accounting and finance practice at the company through new processes, tools, and technology. Jeff covers how he spent his time in the first few years at Bloomerang, including how he approached team building, and then turns to his current priorities now four years in at the company (a big NetSuite implementation!).

After sharing how he approached building a function, Jeff does a deep dive into considerations during acquisitions both on the buy and sell side. He details his extensive experience in acquisitions and highlights some of his best practices and learnings - including how important it is to add nuance and context to the models that bankers develop during the due diligence process.

The episode closes with Jeff sharing the deep detective work he had to do to get to the bottom of one of his weirdest company expense moments early in his career.

For Matt Collis, CFO of PairSoft, storytelling is more than a skill—it’s a strategic tool for aligning teams and scaling businesses. Whether leading acquisitions or guiding cross-functional teams, Collis uses financial narratives to clarify priorities and inspire action. “Someone has to be the storyteller,” Collis tells us, emphasizing how framing financial data in relatable terms helps drive organizational alignment and decision-making.

Collis’ career began in accounting, where he spent seven years honing technical expertise in public accounting. However, he recognized early on that his ambitions extended beyond the technical realm. His transition into leadership roles provided opportunities to engage directly with business leaders, crafting financial strategies that supported operational goals. A pivotal chapter in his career came at Transaction Data Systems (TDS), where he helped the company scale dramatically. Over five years, TDS tripled in size through seven acquisitions, Collis tells us, requiring him to integrate diverse cultures, systems, and processes while scaling the finance team from 10 to 30 members.

At PairSoft, Collis leverages these experiences to prioritize purposeful integration. He sees cultural alignment as key to long-term success, noting that acquisitions can falter without proactive efforts to unite teams around a shared vision. His strategic mindset also focuses on transparency and scalability, ensuring that financial strategies align with operational goals and are clearly communicated across the organization.

Arriving at a high school in Cape Town, South Africa, without speaking English, Cosmin Pitigoi faced an immediate communication challenge. Yet he refused to be deterred, immersing himself in language studies and expanding his vocabulary so he could thrive in the classroom. Years later, that same resolve reemerged in eBay’s IR function, where Pitigoi realized the company’s available data was falling short in communicating the breadth of eBay’s story. This time, Pitigoi immersed himself in the data, adding and fine-tuning metrics that would allow him to better convey eBay’s message.

Before joining Flywire as CFO, Pitigoi spent two decades rotating through leadership roles at eBay and PayPal, building his finance acumen across treasury, investor relations, FP&A, and data analytics. “I never stayed in a single role for more than 18 months,” Pitigoi tells us, describing his drive to learn every facet of the business. By immersing himself in diverse functions, he honed both analytical and communication skills—critical for strategic decision-making.

At eBay, the lack of comprehensive data became a new language barrier, prompting Pitigoi to advocate for stronger data architecture. “Numbers alone can’t tell a story unless they’re accurate and well-organized,” he tells us, underscoring his belief that precise, actionable information fuels effective narratives. This mindset ultimately shaped his approach to finance leadership: be as fluent in data as in interpersonal communication.

Today, at Flywire, Pitigoi champions the idea that true value emerges when finance guides broader organizational goals. His journey from struggling to speak English in Cape Town to optimizing data-driven storytelling at a global fintech highlights a simple truth: conquering communication obstacles—whether linguistic or numeric—can spark remarkable career transformation.