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.