The discussion centers on three CFOs—Don McGuire of ADP, Scott Blackley of Oscar Health, and Patrick Fleury of Terawulf—and their approaches to financial planning and communication. Don McGuire emphasizes ADP's predictable business model, centralizing financial planning to ensure consistent forecasts. Scott Blackley restructured Oscar Health's FP&A to better support a public company, focusing on cost structure and providing actionable insights. Patrick Fleury simplifies Bitcoin mining by using unit economics and is diversifying Terawulf into high-powered compute and AI, positioning the company for future growth. Each CFO tailors their communication to investor expectations, highlighting the importance of matching professional style with organizational needs.

When the opportunity to help lead the corporate travel business at Expedia arose, Regi Vengalil knew it was exactly the role he had been seeking to put his CFO role in gear. Stepping into the CFO position meant overseeing a business unit with $600 million in revenue and $120 million in EBITDA, and Vengalil was eager to take on the challenge. Prior to this, he had been leading a team of strategy and M&A professionals, but the new role offered a much broader scope of responsibility.

“It was a way for me to jump in with both feet to kind of get a full, you know, it wasn’t just a pure FP&A role. I had commercial finance, I had accounting. I even had a systems team. I had financial operations. So it was a full CFO role and a global team that I still knew very well, because I had led strategy for the company,” Vengalil recalls.

This transition marked a critical point in his career. It was only about two years earlier, that Vengalil tells us upon joining Expedia corporate development he immediately became thrust into high-level decision-making, including a meeting with Chairman Barry Diller and CEO Dara Khosrowshahi. During the meeting, Vengalil was tasked with providing input on a strategic deal. After Khosrowshahi expressed support for the deal, Diller turned to Vengalil, who was new to the room, and asked, “Hey, new guy! What do you think?” Vengalil, though it was his first week, confidently laid out the reasons why he thought the deal posed more risk than reward, despite its appeal.

Reflecting on their relationship, Vengalil observed a deep mutual respect between the two leaders, forged during years of close collaboration. Khosrowshahi, who had been with the company for over a decade, had worked closely with Diller on many deals, and Vengalil noted the rapport they shared, particularly in how they approached complex issues.

Diller, known for his sharp insights and high standards, preferred discussions to be clear and lucid. “If you don’t understand the complexity,” Vengalil observed, “you won’t be able to communicate it simply.” This demand for clarity pushed Vengalil to deliver concise, well-reasoned perspectives, an expectation that both challenged and strengthened his leadership capabilities. This early exposure to Diller’s precision-thinking had a lasting impact on Vengalil’s strategic mindset.

In 2012, after nearly two decades in the airline industry, Zane Rowe made a bold career pivot. Leaving behind his role as CFO at United Airlines, Rowe stepped into the tech world, joining Apple in a sales role—a move many saw as risky but one that would ultimately shape his perspective on finance leadership in the digital age. This decision marked the beginning of a transformative journey that prepared Rowe to navigate the complexities of technology, innovation, and data-driven strategies.

Rowe’s time in the airline industry laid a solid foundation for his analytical mindset. Reflecting on his experience, he stated, “I recognized early on the power of data and the power of technology and how it could differentiate a good airline from a bad airline.” As he tackled the capital-intensive, data-heavy world of aviation, he developed an appreciation for how technology and data could unlock operational efficiency. His work on profitability models helped him understand how data could unlock hidden insights, a lesson that would become crucial in his later roles in the tech sector.

In his roles at EMC and VMware, Rowe saw firsthand how technology could revolutionize business operations. His ability to bridge financial expertise with technology adoption became a defining strength. Now, as CFO of Workday, Rowe applies those lessons to the evolving world of artificial intelligence (AI). For him, AI is not just a tool to streamline processes, but a strategic asset that can unlock untapped value, differentiate companies in competitive markets, and drive business transformation.

Rowe views AI as an extension of his long-standing belief in the importance of data. By leveraging AI to analyze massive data sets, CFOs can make faster, more informed decisions. This, he believes, enables finance leaders to be not just stewards of the bottom line but key players in shaping company strategy and future growth. Rowe’s multi-industry career journey, with its blend of traditional finance and cutting-edge technology, has uniquely equipped him to lead in the age of AI.