CFO THOUGHT LEADER

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1090: Broadening the Field: Turning Risk into Reach | Jerome Upton, CFO, Genworth Apr 20, 2025

Show notes

Jerome Upton still remembers the silence that descends just before a game begins. As captain of his college team, he’d scan the huddle, gauge nerves, and ask, “What does winning look like today?” “That’s where I learned the power of shared goals,” Upton tells us. Years later, the Genworth Financial CFO opens staff meetings similarly—then hands teammates room to execute.

The first bold play of his career came soon after graduation. At a small insurer, Upton stunned mentors by jumping to KPMG. “I needed wider fields,” he explains. Eight years of audits sharpened his technical vision, yet the move that truly stretched him arrived when GE Capital—Genworth’s predecessor—offered a divisional‑controller seat with global scope. Overnight his “team” expanded ten‑fold, teaching him to win through trust rather than touch‑every‑file oversight.

International assignments followed: boardrooms in Europe, investor roadshows in Asia, client visits in Latin America. Hearing customers critique products in real time “made finance feel less like a ledger and more like a heartbeat,” he says. That perspective proved vital during Genworth’s post‑crisis crossroads. Tasked with raising capital quickly, Upton orchestrated a minority IPO of a foreign subsidiary, executed at speed and premium valuation. The deal slashed leverage and revealed hidden asset value.

Today his playbook balances share buybacks and debt reduction with growth bets such as CareScout. Multi‑year downside modeling safeguards the core, while his Gretzkyesque mantra—skate where the puck is going—keeps him focused on tomorrow’s opportunity.

1089: Reinventing Operations for Lasting Impact | Brian McClintock, CFO, Fusion Connect Apr 16, 2025

Show notes

t was sixty days into his new role when Brian McClintock tells us he realized the company’s monthly “profit” was actually a million-dollar loss. As the CFO reviewed the financials, he discovered that each rosy figure concealed a troubling truth. For many executives, panic might have followed. Instead, McClintock’s response underscored a key principle: remain calm and stay focused on data-driven solutions.

As he dug deeper, a misalignment of actual costs and revenue assumptions emerged, revealing the precarious financial situation that demanded immediate action. Determined to right the ship, he mapped a bold course, recommending a strategic acquisition that would fortify cash flow and support operational improvements. “We had to leverage operational insights along with our existing relationships,” McClintock explains, adding that his experience in complex telecom environments allowed him to see beyond the numbers. The result was rapid transformation. Within a year, the company went from losing seven figures each month to generating a million dollars in monthly EBITDA—proof of the CFO’s insistence on purposeful change.

1088: Driving Growth with a Builder’s Mindset | Naeem Ishaq, CFO, Checkr Apr 13, 2025

Show notes

It was a first meeting Naeem Ishaq tells us he’ll never forget: stepping into the Chief Product Officer’s office at Salesforce, he began pitching a bold new pricing model. Yet the officer cut him off, bluntly telling him to “figure out the (numbers) first, then we can talk strategy.” Ishaq admits he had inherited something of a mess when it came to the data. Despite the tough feedback, however, he refused to give up. He dove deeper—verifying metrics, updating budgets, and clarifying every detail—determined to show he could be both a financial expert and a strategic partner. By persevering rather than shrinking from the challenge, he eventually earned the trust needed to advance his pricing insights.

That wake-up call echoed lessons he’d learned as a child of immigrants. Ishaq tells us his father arrived in the United States with just twenty dollars, fueled by grit and hope. Growing up, Naeem watched firsthand how determination could unlock opportunity—even if the odds seemed stacked. This conviction led him to form his first business in 1999, forging a passion for technology-driven solutions that would guide him in future roles at Salesforce, Square, and eventually Checkr.

Today, as CFO and Chief Strategy Officer at Checkr, Ishaq’s mindset blends rigorous analysis with an entrepreneurial spark. He believes finance leaders create the most impact when they go beyond reporting numbers to envision what’s possible—and then rally others around that vision.

1087: Why Finance Needs a Seat at Every Table | Tony Jarjoura, CFO, Gigamon Apr 09, 2025

Show notes

It was the kind of boardroom moment that separates finance professionals from finance leaders. Tony Jarjoura, now CFO of Gigamon, found himself surrounded by audit committee members as a dense, highly technical tax strategy unraveled before them. Despite having pored over legal memos and internal reviews, the room still looked puzzled—until Tony spoke. In just two sentences, he distilled thousands of hours of technical effort into a clear, accessible takeaway. “That was the moment,” he tells us, “when I realized the power of translating complexity into clarity.”

Tony’s journey to that moment began with a professor’s advice back in university: go Big Four, earn your CPA, and the world will open up. He took it to heart, spending 15 years at Ernst & Young in San Francisco, embedded in Silicon Valley’s IPO engine room. At EY, he wasn’t just crunching numbers—he was watching ideas travel from whiteboard sketches to billion-dollar listings. Companies like Atlassian, Okta, and Workday became case studies in how finance underpins innovation.

When he stepped into industry during the COVID years, Jarjoura traded IPO war rooms for the operational depths of Gigamon. He jokes about never having recorded a journal entry before—but quickly embraced the inner mechanics of finance operations. Today, he views FP&A not as a rearview mirror but as a GPS system for business decision-making. “Finance has to be the connective tissue,” he says, “translating data into decisions that shape where we go next.

1086: M&A, AI, and the Art of Integration | Adam Ante, CFO, Paycor Apr 06, 2025

Show notes

“It wouldn’t surprise me. No, it would be exciting.”

That was Adam Ante’s initial response when asked if five years from now, he could imagine himself still in the C-suite—but not as a CFO. The comment seemed to linger in the air, hinting at a deeper current in his career journey. Ante, who had led Paycor through an IPO, a pandemic, and most recently, a $4.1 billion sale to Paychex, wasn’t just closing out a CFO chapter—he may have been opening something entirely new.

While he later softened the sentiment, suggesting he might be surprised if he moved beyond finance, his earlier candor revealed a finance leader attuned to operations—and perhaps transformation.

Years earlier, Ante had flown weekly to Colorado, struggling to integrate a newly acquired company. “I felt like I was failing,” he tells us. The lesson was hard-won: strategy and spreadsheets are meaningless unless you can move people with them. That shift—from financial executor to business operator—has defined his trajectory ever since.

His strategic mindset matured further with Extreme Ownership, a book he credits with changing how he approached leadership, cross-functional collaboration, and results.

Now, as the dust settles on Paycor’s acquisition, Ante’s priorities have shifted once again—to preserving what works, aligning teams, and honoring the customer experience.

Controllers Classified: Host Erik Zhou sits down with Amber Papp, VP of Finance at Scentbird Apr 04, 2025

Show notes

Host Erik Zhou sits down with Amber Papp, VP of Finance at Scentbird to explore the unique challenges of accounting in the e-commerce space. From managing a massive inventory of over 700 fragrances to navigating rapid growth and making smart automation decisions, Amber shares firsthand insights on what it takes to keep financial operations running smoothly at a high-growth, subscription-based company.

Amber and Erik also dig into relevant themes like the role of AI in accounting, balancing efficiency with cost when evaluating new financial tools and systems, and the never-ending pursuit of data integrity.

And as the episode closes, Amber shares a truly unexpected budget request—one that involved a Cybertruck, a demolition derby, and a marketing team with big dreams.

1085: The Strategic Power of Curiosity | Erik Rothschild, CFO, Cin7 Apr 02, 2025

Show notes

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.

1084: Reading the Signals, Not Just the Statements | Brian Carolan, CFO, SailPoint Mar 30, 2025

Show notes

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.

The ROI Equation for AI Starts Here - A Planning Aces Episode Mar 28, 2025

Show notes

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.

1083: Navigating the Go-To-Market Roadmap with Precision | Brian Robins, CFO, GitLab Mar 26, 2025

Show notes

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

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