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

One of the key lessons that helped advance Jim Benson down the CFO path was one in clarity and focus during his tenure as FP&A leader for the customer service division of Compaq, freshly acquired by Hewlett-Packard. Eager to influence how the division’s performance was presented, Benson dedicated himself to crafting detailed reports and narratives. However, each time he handed his work to the general manager—a skilled storyteller in his own right—his carefully prepared materials were distilled down to two or three essential points.At first, Benson, a ten year HP veteran, found the process frustrating. “You work very hard to prepare a set of materials and a narrative,” he recalls, “but he would take my materials and build his own narrative.” Yet over time, Benson began to see the value of simplicity and focus, especially in conveying complex financial information to large audiences. The customer service division was in the spotlight for HP’s earnings, so every quarter required a clear, compelling story that was rooted in financial reality and accessible to diverse audiences.Through this process, Benson honed his storytelling skills, learning to construct narratives that cut to the core of the message without sacrificing key details. This foundational experience shaped his leadership style, setting a high standard for strategic communication throughout his career. Today, as CFO of Dynatrace, Benson applies these skills to ensure that every financial story aligns with the company’s mission, balancing growth, profitability, and innovation.

Had Martin Nolan studied engineering instead of accounting, his career might never have intersected with icons like Marilyn Monroe, John Lennon, or Michael Jackson. Born and raised in Ireland, Nolan’s journey to becoming CFO of Julien’s Auctions, the world’s leading entertainment auction house, was as unique as it was unpredictable. His path to New York City—and ultimately to Julien’s—was made possible by a Green Card lottery, not an accounting degree.Upon arriving in New York in the early 1990s, Nolan worked at the front desk of the New York Hilton, immersing himself in American culture. Through determination and networking, he ascended into the finance world, becoming a stockbroker and investment advisor at firms like JP Morgan Chase and Merrill Lynch. Yet, when he met Darren Julien in 2004, everything changed. Julien was running a Johnny Cash auction and, as Nolan explains, “He was a marketing guy who needed a finance guy, so I joined him.”The following year, Nolan resigned from Merrill Lynch to join Julien’s Auctions as CFO—a decision met with surprise from his Wall Street colleagues, who questioned the risks. But Nolan saw no difference between auction halls and stock exchanges, where buyers and sellers converge. By 2010, he became an equal partner in the business, embracing the risks and rewards of the auction world.Today, with Julien’s at the forefront of entertainment memorabilia, Nolan’s journey highlights a unique blend of finance acumen, adaptability, and an enduring sense of adventure—a career truly shaped by chance and daring choices.

In this episode of Controllers Classified Erik Zhou explores the role of accounting in scaling businesses as well as public company accounting processes with Eric Van Cleve, Controller at 8x8. The episode begins with a recap of Eric’s career in accounting, detailing his discovery of accounting in college and how he worked his way up the ladder once he landed client side out of college. He notes that he found the most success when he focused on being interested, proactive, curious and capable.The episode then turns to a discussion on how to think about directing accounting operations at scaling companies. Eric shares how he thinks about team structure to ensure efficiency in the close process as well as his decision making framework for where to automate and where to offshore. In every decision he tries to factor in not just current but also future business needs.From there, the discussion deep dives into private vs. public company accounting, with Eric providing advice to finance and accounting leaders at pre-IPO companies regarding what to prioritize as they think about SOX readiness. He notes that these companies must be able to confirm that the answers they get to in their data are in fact the right answers. In other words, teams have to be able to prove out their control processes and ensure that reporting obligations can be met. And of course, teams should familiarize themselves with 10Ks and 10Qs.

When it came to the public markets, no one can accuse David Morris and his seasoned C-suite colleagues, Fred Burke and Kendall Forbes, of being impatient. Guardian Pharmacy Services, a company they built from the ground up, recently raised $112 million in an IPO, listing on the NYSE under the symbol “GRDN.” The milestone reflects a culmination of over three decades of ever thoughtful, strategic decision making in a highly specialized market.For CFO David Morris, the path to the public markets wasn’t about rapid scaling or chasing quick wins. “We knew from the start that success in healthcare is a long game,” he says, underscoring the team’s deliberate approach. CEO Fred Burke, COO Kendall Forbes, and Morris founded Guardian Pharmacy with the understanding that meaningful growth would come through a patient, steady process of building relationships and refining operations. They entered a complex space, providing technology-enabled pharmacy services for long-term care facilities (LTCFs) across the U.S., from assisted living to behavioral health facilities.Today, Guardian’s 50 pharmacies serve approximately 174,000 residents in 6,700 facilities across 36 states. With more than two-thirds of its revenue coming from assisted living and behavioral health facilities, Guardian has become a trusted partner in the long-term care industry, where patient care and regulatory oversight demand careful attention.The IPO marks a new chapter for Guardian, yet Morris, Burke, and Forbes remain dedicated to their original mission. As the company grows in the public eye, their focus remains on delivering results through quality service and operational insight, underscoring the patient leadership that has driven Guardian’s success.

Sitting quietly at the back of a crowded GE conference room, a young Sandra Wallach diligently took notes during an executive briefing. As one of the newest inductees into GE's esteemed Financial Management Program (FMP), she was eager to absorb every detail. Unbeknownst to her at the time, this moment marked the beginning of a transformative 17-year journey with General Electric."FMP allowed me to figure out what I really like to do, what I gravitate towards, and what I'm not as interested in," she reflects. From aircraft leasing to manufacturing finance, each rotation broadened her expertise and honed her adaptability.GE's approach to talent development was immersive and expansive. Wallach continues, "I had 10 different roles in nine different physical locations over my time." This constant movement not only built her resilience but also provided her with a holistic understanding of GE's diverse businesses. The culture emphasized being an integral part of the senior leadership team and driving change. "They expected me to be able to speak to the business almost as well as the leader that I was supporting," she notes.This high standard pushed her to develop skills beyond traditional finance roles. Along the way, Wallach says GE's culture exposed her to the personal attributes that would become increasingly critical as she advanced into leadership positions. "Do you have personal edge? Can you make the tough calls? Do you have personal energy?" she explains. Serving as a Master Black Belt and later as a pricing executive, she stepped outside traditional finance roles, gaining valuable insights that would later prove essential in the C-suite.Beyond GE, Wallach tells us there were still a few boxes to check before she could step into a CFO role. Positions at Intuit and MiaSole provided her with exposure to Silicon Valley's fast-paced culture and the opportunity to work directly with boards and investors. These experiences, coupled with her GE foundation, ultimately paved the way for her appointments as CFO of Amprius Technologies.

In the latest Planning Aces episode, hosts Jack Sweeney and Brett Knowles discuss how finance leaders are elevating FP&A as strategic partners within organizations. Featuring insights from CFOs Regi Vengalil, Matt Steinfort, and Isabelle Winkles, the episode highlights themes like the importance of reliable data, setting constraints to enhance strategic planning, leveraging AI in finance, real-time collaboration, and educating business units. The CFOs emphasize Finance's role in guiding better decision-making and aligning organizational goals.

It was not the first time John Gronen addressed the staffing company’s board — but it was very likely the most consequential. At the time, Gronen was vice president of finance, responsible for assessing acquisitions and analyzing their outcomes. The company operated two businesses: one generating about $30 million in EBITDA, while the other incurred annual losses of roughly $10 million. Gronen proposed a strategy to merge the two operations, consolidating efforts to increase profitability.Once the board approved the plan, Gronen led efforts to align sales teams and streamline processes. In just a few days, he and the leadership team developed a plan to reduce overlapping costs and improve operational efficiency. The merger cut $10 million in expenses, turning the combined business into a more profitable operation that was ultimately sold to a public company.This experience shaped Gronen’s career, reinforcing his commitment to taking on complex challenges and thinking beyond traditional finance roles. Looking back, Gronen tells us his involvment with M&A began during his time at Alltel, where he contributed to a number of M&A transactions. Subsequent roles at Technosource and VPay expanded his skills into operations, sales, and human resources, giving him the well-rounded experience necessary for senior leadership.Now serving as CFO of Yooz, Gronen draws on this experience to focus on scaling the company through automation, AI-driven processes, and product expansion.

When David Eckstein inherited a struggling business unit earlier in his career, he faced an uphill battle. The unit wasn’t one he had built, nor had he developed the frameworks or discounting policies in place. Yet, it was hemorrhaging money, and Eckstein quickly realized he had to act. “Just because you inherited the business doesn’t mean it’s not yours,” he says. “And you shouldn’t be thinking in terms of, you know, this isn’t mine.”The first challenge was identifying the root of the problem. Was it high commissions? Support costs? After careful analysis, Eckstein uncovered the crux of the issue: the business was operating with a negative gross margin. Several factors were to blame, including a lack of control over discounting. “One person had full control over whether they gave an 80% or 20% discount,” he explains. “We needed to implement levels and thresholds to bring structure to the process.”In addition, Eckstein found that the company hadn’t properly evaluated its costs to serve customers. Key personnel were misaligned to the cost of goods sold (COGS), and the company wasn’t capitalizing research and development (R&D). “We had to reassign resources to the right areas and ensure our investments aligned with revenue goals,” he recalls.The experience reinforced Eckstein’s belief that leadership means taking full responsibility, even when circumstances are inherited. “You need to embrace change and the outcome,” he reflects. “That’s the only way to create ownership and drive meaningful results.” Through these efforts, Eckstein began to repair the business unit’s trajectory, validating that accountability and decisive action are essential to strategic leadership.

In his three years as CFO of Packer Fastener, Brian Hogeland has led a milestone transformation of the company’s financial operations. Joining in 2021 during a period of rapid growth, Hogeland quickly identified opportunities to streamline processes, align business goals, and introduce technology-driven solutions. With Packer Fastener’s quirky culture—known for slogans like “We’ve got the biggest nuts in town”—Hogeland’s mission was to bring structure without losing the fun spirit at the company’s core.Hogeland’s strategic mindset reflects his career-long blend of finance and technology expertise. Early in his tenure, he introduced NetSuite as the company’s ERP system, replacing manual processes that once took weeks with real-time data and automation. This shift provided leadership with instant visibility into revenue, helping drive smarter, faster decisions across Packer Fastener’s growing network.Hogeland also emphasized data-driven planning. His approach aligns financial metrics with operational indicators like employee productivity and vehicle profitability. This framework enables intentional, forward-thinking strategies, ensuring the company scales efficiently without wasting resources.Throughout his career, Hogeland has championed innovation—whether through cloud-based tools or AI modeling—making finance a proactive force for growth. His ability to blend financial discipline with technology has better positioned Packer Fastener for sustainable growth in the years ahead.

In January 2020, most finance leaders saw ASC 606 as a closed chapter. However, for Braze’s newly appointed CFO, Isabelle Winkles, the revenue recognition standard became front and center. While ASC 606 was merely a speedbump for seasoned professionals—especially for a 25-year finance veteran like Winkles—it posed a notable challenge within Braze. Many employees had never worked at a public company that had adopted the standard, making it a crucial area where alignment and understanding were essential.Winkles recognized that her role wasn’t just about managing finances—it was about educating and aligning teams across the organization. She knew that technical rules alone wouldn’t resonate with the sales team. Instead, she framed the conversation around tangible business impacts: “You have to explain to the sales team, ‘Hey guys, if we start giving people too much time to pay, this is going to change our financial profile, and we will be valued differently by the market as a result.’”By connecting financial nuances with outcomes that mattered—like market valuation and compensation—Winkles ensured her message landed. “And you start explaining that to people,” she added, “and they say, ‘Oh, okay, so this will change the stock price valuation ultimately, and that impacts my compensation.’”For Winkles, the key wasn’t just mastering technical details but crafting a message the broader organization could digest and act upon. Success came from engaging teams across functions, fostering alignment, and ensuring every part of the organization understood the financial implications of their actions.