1,031: Unlocking Operational Scale in Health Insurance Through AI and Data | Scott Blackley, CFO, Oscar Health

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.

In 2018, Daniel Welch made a life-altering decision. After a decade in investment banking, working on high-profile IPOs and M&A deals at Morgan Stanley, Welch found himself at a crossroads. The birth of his daughter and a health scare involving his father led him to question the career path he was on. “I was mentally stimulated by the work, but it didn’t align with my personal values,” Welch reflects. Burnt out and seeking more purpose, he left the corporate finance world to pursue mission-driven opportunities in the health and wellness sector.Welch’s career pivot first brought him to Sonos, where he helped lead the company through its IPO. He later transitioned to Oura, the maker of the Oura Ring, guiding the company through a critical growth stage. These experiences solidified his desire to combine financial expertise with personal passion.In 2022, Welch found his ideal role as CFO of Kate Farms, a plant-based medical nutrition company revolutionizing the field. Kate Farms focuses on providing organic, plant-based nutrition products, free of common allergens and designed to improve health outcomes for patients in medical need. Its mission resonated deeply with Welch’s personal health journey, which began with his transition to a plant-based diet.Backed by investors like Goldman Sachs Private Equity and Novo Holdings, Kate Farms continues to grow its presence in hospitals and home care systems across the U.S., making Welch’s leadership integral to the company’s scaling efforts. His career transformation highlights how purpose and profit can intersect when leadership is guided by personal values.

When Deanna Strable was approached to take on the role of CFO at Principal Financial Group, she was taken by surprise. Having spent most of her 30-year career in leading business units rather than focusing on finance, Strable initially questioned whether she was the right fit for a position traditionally held by financial experts.“Ultimately,” she recalls, “what I learned from our board and CEO was that they really wanted someone who could partner with them in driving the company forward—someone who had the ability, obviously, not only to understand the financials but also to be able to do so within the context of appreciating and analyzing how the day-to-day impact of our operations on our financials related to our long-term strategy.”This blend of operational insight and financial expertise would come to define her tenure as CFO. Over her 7 years in the role, she led the company through significant strategic shifts. Under her leadership, Principal exited underperforming and commoditized businesses, such as retail annuities and individual life insurance. These moves were part of a broader plan to focus the company on areas with greater long-term-growth potential, including retirement solutions and asset management.Strable also reshaped the company’s financial priorities, moving beyond a narrow focus on earnings growth to a broader set of metrics, including return on equity, capital allocation, and customer satisfaction. Her emphasis on optimizing multiple metrics, rather than chasing short-term financial gains, helped to lay the groundwork for sustainable success. Strable’s career journey as CFO was a testament to the power of strategic thinking in driving both financial and long-term business growth.

Ben Averis’s journey to CFO of Yoto was shaped by diverse experiences in finance, ranging from his early days at PwC in mergers and acquisitions (M&A) to leading roles in private equity-backed businesses. His exposure to the "buy and build" strategy during M&A transactions taught him the challenges of scaling businesses while maintaining their core values. Ben worked on transactions that involved integrating smaller, family-run businesses into larger corporate structures. This experience revealed to him a key risk: while larger companies could gain operational efficiencies, they often lost the customer-centric magic that made smaller businesses special.Reflecting on these experiences, Ben noted, "What you would find is that, if you got to that buy and build moment, and you integrated (the businesses), some of the magic would be lost, and you would lose a bit of the customer obsession." This insight has become central to his strategic mindset as CFO of Yoto, a founder-led company with a strong customer-first philosophy.Ben’s understanding of the "buy or build" moment shapes his leadership at Yoto, where he balances the need for growth with preserving the company’s entrepreneurial spirit. He recognizes the unique passion founders bring, especially their deep connection to customers, which can be diluted in corporate acquisitions. As Yoto scales, Ben is committed to ensuring that this customer obsession remains at the heart of the business, reinforcing that a well-run founder-led company often thrives because of its focus on delivering tailored customer experiences rather than sheer scale.

It was during the first half of 2024 that press reports first surfaced to suggest that Bitcoin pioneer TeraWulf was seeking to make a bold strategic pivot into AI and high-power compute. Along the front lines of this move stood Patrick Fleury, TeraWulf’s action-oriented CFO, whose short tenure at the firm thus far has been notable for its aggressive cost-cutting measures and bold efforts to address the company’s debt. Moreover, Fleury’s focus on the optimization of the cash flow from TeraWulf’s Bitcoin-mining operations has proved crucial in stabilizing the company during turbulent market conditions.It is perhaps surprising to learn—given his success as a CFO—that Fleury had not always envisioned himself in this role. Having spent 16 years as a strategic investor, he had been content in working from the sidelines, guiding companies through investments and strategy. Becoming a public-company CFO had never been on his radar. Still, when TeraWulf needed a leader to guide it through significant challenges, his deep understanding of financial markets and investment strategy turned out to make him the ideal choice.Fleury’s unique investor mind-set has been instrumental in charting TeraWulf’s new growth trajectory. His ability to engage investors, simplify complex industry dynamics, and clearly demonstrate “value” has been key to gaining investor buy-in for TeraWulf’s new direction. Moreover, his experience on the buy-side has provided him with valuable insight into what investors look for—transparency, potential for growth, and clear financial discipline.This ability to communicate effectively, coupled with his strategic acumen, has allowed Fleury to lay the groundwork for TeraWulf’s shift into AI and high-power compute. By looking at decisions through an investor’s lens, he has garnered the ability to build trust with stakeholders while at the same time positioning TeraWulf as a forward-thinking player in the rapidly evolving AI and data center sectors. Fortunately for his firm, Fleury’s financial leadership continues to drive TeraWulf toward a promising future in these high-growth markets. 

When Scott Blackley was asked in kindergarten what he wanted to be when he grew up, his answer was surprisingly clear: “I want to be an auditor.” This early ambition was no coincidence; his father was a partner at KPMG, and young Blackley grew up around the firm’s offices, imagining himself one day sitting at a big desk, overseeing important work. True to his dream, he eventually ended up following in his father’s footsteps to become a partner at KPMG and invest a dozen career years there.Despite achieving his childhood goal and carrying on the family legacy, though, Blackley eventually found himself at a crossroads. “It was a tough decision to leave KPMG,” he recalls, “but some of the experiences that I had had involving other people’s business problems had made me want to own them.” This realization marked a turning point in his career that fueled his desire to take on more responsibility and solve problems on a firsthand basis.This drive led Blackley to Oscar Health, where he stepped into the CFO role during a pivotal moment. Reflecting on his early days at the company, Blackley observes, “When I joined, one of the things that I walked in the door with was a commitment to myself that I was going to be thoughtful about taking the time to understand the situation and then decisive about making decisions.” Consequently, within 90 days, he would end up reorganizing the finance function to separate FP&A from the controller’s office and hiring a new leader to build a more structured finance organization—one capable of supporting Oscar Health’s ambitious plans for growth and transformation.

In 2021, Don McGuire received an unexpected call from ADP's HR leader, offering him the In 2021, ADP’s HR leader reached out to Don McGuire, then the company’s globe-trotting EMEA In 2021, ADP’s HR leader reached out to Don McGuire, then the company’s globe-trotting EMEA president, to gauge his interest in stepping into the firm’s CFO role. McGuire was surprised, inasmuch as it had been nearly two decades since he had veered off the traditional finance career track. During this interim, McGuire had taken on various global leadership roles far removed from the typical CFO pathway.However, as the former CFO of ADP Canada, McGuire was by no means an unlikely candidate. Still, the leap from being CFO of a single geography to being CFO of an entire publicly traded corporation would be significant, and McGuire’s experiences along his unique previous journey served to make the unexpected offer to him only more intriguing.As it turns out, back in 2002, while serving as CFO of ADP Canada, McGuire had come to a similar crossroads. Although his career in finance had been progressing smoothly, his curiosity about the broader business landscape had led him to consider a different direction. Encouraged by his superior, ADP Canada’s president—who had noticed McGuire’s strong rapport with clients during joint meetings—McGuire took a leap of faith, stepping out of his finance role and into a client services leadership position. Taking on this mission—devoid of a “C” title—was a calculated risk, but McGuire believed that by immersing himself in the operational side of the business, he could gain valuable insights and broaden his leadership skills. Very consequentially, this move allowed him to engage directly with clients, manage teams, and drive business outcomes in ways that traditional finance roles seldom offer.This bold decision set McGuire on a unique career path, ultimately equipping him with the diverse experiences that would make him an ideal candidate for ADP’s CFO role nearly 20 years later.

In this bonus episode of CFO Thought Leader, host Jack Sweeney shares insightful stories from three finance leaders, focusing on their early beginnings and how those experiences shaped their careers. Scott Healy reflects on the influence of his father, an Air Force colonel, and his deaf brother, both of whom instilled a strong work ethic and a spirit of perseverance. Tracy Curley discusses her non-traditional path, balancing business experience with academic pursuits while navigating the challenges of being a military spouse. Lastly, Svai Sanford recounts his journey from being a Laotian refugee with a third-grade education to becoming a CFO, thanks to the support of his foster family. Each story highlights the significance of resilience, family influence, and the transformative power of education and opportunity.

In this episode of Planning Aces, Jack Sweeney and Brett Knowles discuss the evolving role of FP&A professionals, emphasizing the importance of relationship-building and strategic collaboration within organizations. As summer ends and fall approaches, Brett predicts a surge in business activity, particularly as companies rush to meet year-end objectives. The conversation highlights the decline in travel post-COVID, with more business being conducted via web meetings, though these are often less effective than in-person interactions. Brett underscores the need for FP&A teams to prepare thoroughly for meetings and to foster diverse thinking to achieve better outcomes. The episode also explores the challenges of integrating acquisitions, the significance of continuous improvement, and the evolving responsibilities of FP&A leaders. Ultimately, the discussion centers on the importance of strategic relationships, effective communication, and adaptive leadership in navigating today’s complex business environment.