Fresh out of a hedge fund analyst role, Erik Rothschild walked into an interview at a Chicago-based trading firm and did something unexpected—he pitched actual trade ideas to the portfolio manager across the table. That bold move earned him a spot on the team, and eventually, a portfolio of his own. “That whole experience taught me how to assess decisions through the lens of an investment,” Rothschild tells us. It’s a mindset that has quietly shaped every leadership decision he’s made since.

Rothschild’s early career was forged in the high-stakes world of investment finance during the 2008 financial crisis. He later transitioned into corporate finance, helping build out the FP&A function at Sovereign. When the CFO unexpectedly departed, Rothschild found himself reporting directly to the CEO—presenting financial results to the board and leading a complex equity raise. “It was both exciting and stressful,” he recalls, “but I knew I had a window to gain experience that would last a lifetime.”

What sets Rothschild apart is the investor’s mindset he brings to the CFO role at Cin7. He encourages his team to think in bets—evaluating risks, testing hypotheses, and acting decisively. He’s also a champion of simplicity and automation, challenging his team to reduce low-ROI cycles and focus on what matters most.

It was a late-night meeting room lit by the glow of Excel spreadsheets and half-empty coffee cups. Brian Carolan, then a rising finance leader, looked around the table and saw not just fellow accountants and analysts but a collection of people relying on him to bridge data and strategy. In that moment, he felt the weight of a CFO’s responsibility keenly. “Finance is never only about numbers,” Carolan tells us. “It’s about connecting the dots for everyone in the room.”

Years earlier, he had traded the security of a Big Four firm for a nascent startup, learning quickly that growth rarely follows a neat script. One day, he might be projecting cash flow; the next, mending fractured vendor relationships. Each challenge Caloran tells us strengthened his conviction that adaptability drives sustainable success. He carried that lesson into a complex M&A deal, where he orchestrated integration across multiple departments. “M&A isn’t just consolidation,” Carolan tells us. “It’s a chance to redefine the culture, if you’re willing to listen.”

As his influence grew, Carolan found that effective CFOs serve as translators—turning raw data into forward-looking stories. After a particularly tense board presentation, he recalls a mentor pulling him aside. “Numbers matter, but so does the narrative behind them,” the mentor said. That advice remained Carolan’s compass. In every leadership role since, he has championed an inclusive approach, ensuring finance is a unifying force that galvanizes operations, sales, and strategy under one clear vision. And that, Carolan tells us, is how real transformation takes root.

In this episode of Planning Aces, three forward-looking finance leaders share how they’re transforming planning and forecasting inside their organizations. CFO Kevin Rhodes of Extreme Networks discusses the dual lens through which he evaluates AI—external monetization and internal productivity. Brendon Sullivan, CFO of 2X, reveals how a post-PE investment reality check led him to pioneer a weekly reporting cadence to drive faster decision-making. Meanwhile, Gabi Gantus of Mytra AI draws on her Tesla FP&A roots to illustrate how finance can lead long-term operational planning. Brett Knowles joins Jack Sweeney to unpack key insights and the broader implications for FP&A.

Co Host Brett Knowles emphasizes the need to distinguish internal and external AI use cases, applauds CFOs who are expanding AI’s role beyond headcount reduction, and highlights how AI can sharpen decision-making and compress process cycles. He underscores the CFO’s evolving role in overseeing cross-functional strategy, particularly as AI accelerates organizational complexity. From sales effectiveness to real-time alerting, Knowles sees AI as a vital lever in both financial performance and agility, cautioning laggards that competitors are already moving ahead.

It was a pivotal moment Brian Robins tells us he’ll never forget: stepping onto a makeshift stage to address some 400 employees just minutes before a key 8-K filing would publicly announce the potential sale of a major business unit. The room bristled with anxiety—people worried about their jobs and the future of the company. Robins recalls that, instead of relying on scripted talking points, he spoke from the heart and vowed to keep everyone informed as events unfolded. By offering that openness, he reinforced his belief that finance isn’t just about numbers, but about building trust and forging a clear path forward.

Today, that spirit of transparent communication fuels Robins’s approach as CFO. Above all, he prioritizes strong relationships across every organizational function, from sales and marketing to product and engineering. This is why go-to-market execution, he explains, has become the centerpiece of his strategic leadership. Robbins embeds dedicated finance professionals alongside revenue-focused teams, helping to fine-tune territory splits, refine pricing, and calibrate product positioning based on real-time data. Now Listen

Tim Arndt still remembers the urgency in the air when AMB Property Corporation decided to merge with Prologis at the height of the financial crisis. It was, as he describes, “a merger of equals,” but Arndt tells us that, in the end, it was the legacy management of AMB that would lead the newly formed Prologis.

The “equal” nature of the deal belied a deeper reshuffling of leadership, with AMB’s team rising to steer the new entity and Arndt finding himself on the CFO path.

Fresh from this integration, Arndt tells us, he learned one of his most valuable lessons: staying agile and raising your hand for new opportunities is critical when your environment is in flux. He found himself immersed in evolving structures, from investor relations to strategic funding, honing a flexible leadership style that balanced risk management with forward-thinking vision.

Today, as CFO of Prologis, Arndt credits this experience for shaping his strategic mindset. By leaning into the complexities of merging companies—where cultures, processes, and people collide—he discovered that strong financial leadership isn’t just about spreadsheets and metrics; it’s about stewarding a newly formed organization toward stability and growth. That early trial taught him to embrace change rather than fear it, which is precisely how he continues to guide Prologis into future opportunities.

It was a moment that would shape Erik Swenson’s approach to finance forever. As a co-op student at Northeastern University, he found himself in front of a room full of engineers, presenting financial metrics he had carefully compiled. When the meeting ended, one of the engineers approached him and said, “That was interesting, but it doesn’t mean anything to me. I make the product.” The comment struck a nerve. Driving home that evening, Swenson couldn’t shake the realization—numbers alone don’t drive a business; they need to connect to the people building it.

That early lesson in financial storytelling set the foundation for a career built on bridging finance with operations. Swenson tells us his path wasn’t a straight line—he originally pursued computer science before pivoting to economics and then accounting. After early roles in financial analysis, he spent 15 years moving through finance leadership positions at Danaher, where he sharpened his ability to translate financial insights into business decisions.

When IDT tapped him to be CFO in 2018, Swenson faced a challenge that tested his adaptability. As he tells us, the company had a strong accounting foundation but needed deeper financial analysis to support its innovation-driven growth. He immediately set to work embedding finance into IDT’s decision-making, ensuring the function wasn’t just reporting numbers but helping shape the company’s strategic direction. “It’s not just about getting the numbers right,” Swenson explains, “it’s about making sure those numbers mean something for the business.”

It was a moment of “shock and awe” that Jason Lee says shapes his strategic mindset. Soon after joining Square, he discovered a major partnership with Starbucks that was quietly bleeding millions of dollars and threatened Square’s financial runway. “We had to swarm the problem,” Lee tells us. The team renegotiated terms and preserved the company’s stability—a crucial lesson in vigilance and swift action.

Lee’s path to that pivotal juncture began in investment banking and private equity, where he gained perspective on what makes companies thrive. Years later, as he moved from corporate development into investor relations and financial strategy at Square, he refined his approach to measuring ROI, understanding key business drivers, and aligning capital investment with sustainable growth. During Square’s IPO process, Lee learned how investor feedback refines product strategy and strengthens customer relationships.

Today, as CFO of Faire, Lee keeps the same principle front and center: gain visibility first. “If you don’t know where your money goes, you can’t optimize the outcome,” he tells us. This insistence on clear metrics is part of a broader philosophy that financial leaders must do more than simply balance books. They must articulate how each investment—whether for short-term gains or long-term positioning—serves an overarching goal.

That pragmatic yet visionary perspective is evident in Lee’s readiness to address risk head-on, allocate resources smartly, and engage stakeholders with clarity. In his view, a successful CFO not only safeguards the bottom line but fosters an

The moment 2X secured private equity backing in March 2023, CFO Brandon Sullivan knew expectations would shift overnight. “There’s gonna be a press release,” he remembers thinking. “Our new PE partners will open up a treasure chest of relationships for us—we need to be ready.”

In anticipation, Sullivan and his team ramped up hiring, ensuring 2X had the supply of talent needed to meet the expected surge in demand. But in the six months spent navigating investment negotiations, pipeline oversight had faltered. Revenue didn’t spike as expected. Instead, churn crept up. “We had holes we hadn’t paid attention to,” Sullivan tells us. “And the benefits we thought would be immediate weren’t—they needed time to take root.”

The result? A painful lesson in timing. They had staffed up, but business momentum had stalled, sending gross margin percentages downward month after month. The wake-up call came swiftly—a tough conversation with the PE board. “It was needed,” he admits. “The realization hit: Monthly reporting was too infrequent for a dynamic business like ours.”

Stuart Leung had occupied the CFO office at Flexport for only a few months when he realized the supply chain management company’s growing margin pressures stemmed not from a single root cause but from many. From pricing misalignment to invoice errors, Leung had compiled a lengthy list of snags. Along the way, he began empowering the people closest to each issue to drive the necessary improvements. By implementing more than 15 “big rock” initiatives—tracked through monthly reviews—Flexport rapidly identified, tested, and refined solutions. This cross-functional, data-centric effort not only began restoring margins but also created a replicable model of continuous improvement.

That turnaround effort, Leung tells us, echoed lessons he learned earlier in his career. As a young analyst at an investment bank, he quickly discovered how fundamental analysis and modeling could uncover hidden risks. Later, private equity taught him the vital link between operational decisions and financial outcomes—a perspective he solidified while leading finance and supply chain for a small consumer brand. When he encountered Flexport as a paying customer, its tech platform so thoroughly simplified his logistics challenges that he became a believer in its end-to-end visibility.

Trintech CFO Omar Choucair is increasingly turning to AI as a strategic advantage—building teams, refining data “plumbing,” and automating time-consuming processes. His strategic mindset, honed by years of thriving in unpredictable environments, drives him to embrace AI as a catalyst for operational efficiency and transformative growth. Choucair tells us that his approach centers on leveraging AI to unlock competitive insights, streamline decision-making, and propel Trintech ahead in the rapidly evolving landscape of finance and technology.

It was an impromptu meeting Gantus will never forget. One day at Tesla, the company’s then-President of Automotive, Jérôme Guillen, pulled her aside, whispering about a decision Elon Musk was leaning toward. Guillen—who led the automaker’s push for production scale and supply chain agility—believed a different path could better serve the company, but needed someone with operational and financial data at her fingertips. “Let’s go talk to him—just you and me,” Guillen said. Standing before Musk, Gantus walked through cost impacts and strategic trade-offs, methodically highlighting why their plan would outperform the existing direction. She recounts feeling a rush of excitement when Musk ultimately changed course, calling it key to her growth.

That moment encapsulates Gantus’s rapid ascent from Tesla’s first corporate FP&A hire to a finance leader shaping billion-dollar decisions. Her approach has always been about embedding finance in day-to-day operations, whether rethinking shift schedules, optimizing inventory, or forging data-driven paths for emerging initiatives. Sitting alongside engineers and factory managers, she became a trusted partner who refused to let finance stay locked in spreadsheets.

Today, as CFO of Mytra AI, Gantus carries forward the mindset that made her indispensable at Tesla. She now steers Mytra AI’s efforts to secure large warehouse contracts and streamline supply chain workflows, forging growth paths. She’s determined to refine her new company’s cost structures, champion a culture of close collaboration, and leverage every insight from the operational trenches. It’s a philosophy built on pragmatism, strategic thinking, and unwavering perseverance—one that began with a tap on the shoulder, data-driven vision, and a fearless willingness to challenge the status quo.