CFO THOUGHT LEADER

Ashim Gupta, who has evolved from a pre-IPO CFO to now serving as both CFO and COO, is busy redefining the role of finance in driving growth and innovation. Initially focused on strict financial discipline, Gupta’s responsibilities have expanded to integrate long-term growth initiatives with day-to-day operational execution.In our discussion, Gupta explains that funding AI projects at UiPath is guided by a rigorous evaluation framework. “We assess every project based on scalability, efficiency, revenue impact, and strategic differentiation,” he tells us. This disciplined approach ensures that each AI investment not only delivers measurable ROI but also aligns with UiPath’s broader vision of merging AI with automation.Transparent communication with the investment community has been key to this evolution. Gupta emphasizes that clearly articulating milestones and performance metrics is essential as the company’s narrative shifts from its RPA origins to becoming a leader in AI-driven automation, he tells us. This transparency builds trust and demonstrates the strategic value behind each investment decision.Moreover, Gupta’s dual role enables him to balance aggressive AI R&D investments with the demands of core operational priorities. By bridging finance and operations, he ensures that strategic initiatives are effectively executed while maintaining robust financial discipline. As UiPath continues to push the boundaries of automation, Ashim Gupta’s strategic mindset remains central to its sustained success and innovation in the evolving digital landscape.

Like many seasoned finance executives, Damon Fletcher saw Snowflake as a game-changer in cloud-based data management. While a senior finance executive at Tableau, he championed its adoption, recognizing its ability to scale analytics and streamline enterprise data operations. But he also discovered a challenge familiar to many finance leaders—the hidden costs that come with cloud consumption-based pricing.At Tableau, Fletcher tells us, the company’s Snowflake costs grew exponentially, mirroring a broader trend in tech where companies struggle to control cloud spend. This realization led Fletcher beyond the CFO office. In 2023, he co-founded Caliper, a company dedicated to bringing greater cost transparency and AI-powered efficiency to cloud spending.Fletcher tells us that AI is central to Caliper’s approach. The platform leverages machine learning forecasting to predict cloud usage trends and generative AI to surface actionable cost-saving recommendations. Unlike traditional cloud cost tools, Caliper provides deep insights across Snowflake, AWS, and Datadog, allowing finance and DevOps teams to pinpoint inefficiencies in real time.

Early in his career, Lior Maza chose to immerse himself in smaller, venture-backed startups instead of large enterprises—a move that exposed him to an array of responsibilities, from fundraising, recruiting to crisis management. “When you’re in a small team,” Maza tells us, “you end up doing everything, and that’s where the agility mindset really takes root.”Years later, after honing his skills in larger organizations, he joined Priority Software, an established yet agile cloud ERP firm. Under his guidance, the finance function embraced new performance measurements—focusing on recurring revenue, net retention, and churn—to manage a transition from traditional licensing to a SaaS model. “Agile finance leadership,” Maza tells us, “is about looking beyond immediate metrics and creating frameworks that drive long-term value.”

Bill Korn approaches board leadership with the same strategic, forward-thinking mindset that defined his CFO career. He believes a board member's role extends beyond governance to actively supporting company growth, shaping financial discipline, and guiding leadership teams through inflection points. Bill prioritizes long-term value creation over short-term gains, leveraging his M&A expertise, IPO experience, and global operations knowledge to help companies outmaneuver larger competitors. He advocates for hiring and retaining top talent, using technology as a competitive advantage, and fostering a culture of transparency and accountability—ensuring that businesses not only grow but sustain their success in evolving market conditions.

In this episode of Controllers Classified, host Erik Zhou sits down with Jeff Arensman, Controller at Bloomerang, to cover two important topics: building a finance function from scratch and the role of finance in acquisitions.For Jeff, the two are inextricably linked at Bloomerang. As the first finance hire at the company, his first task was supporting an acquisition that needed to close in just three weeks. He then quickly turned to building a strong foundation for the accounting and finance practice at the company through new processes, tools, and technology. Jeff covers how he spent his time in the first few years at Bloomerang, including how he approached team building, and then turns to his current priorities now four years in at the company (a big NetSuite implementation!).After sharing how he approached building a function, Jeff does a deep dive into considerations during acquisitions both on the buy and sell side. He details his extensive experience in acquisitions and highlights some of his best practices and learnings - including how important it is to add nuance and context to the models that bankers develop during the due diligence process.The episode closes with Jeff sharing the deep detective work he had to do to get to the bottom of one of his weirdest company expense moments early in his career.

Matt Collis, CFO of PairSoft, is a SaaS expert specializing in accounts payable automation. He discusses storytelling as a strategic tool for aligning teams and scaling businesses. Collis shares insights on the importance of cultural integration during acquisitions and how transparency in financial narratives drives decision-making. He also highlights leveraging AI for procurement efficiency, emphasizing cash flow management and the shift from an accountant to a dynamic financial leader.

Arriving at a high school in Cape Town, South Africa, without speaking English, Cosmin Pitigoi faced an immediate communication challenge. Yet he refused to be deterred, immersing himself in language studies and expanding his vocabulary so he could thrive in the classroom. Years later, that same resolve reemerged in eBay’s IR function, where Pitigoi realized the company’s available data was falling short in communicating the breadth of eBay’s story. This time, Pitigoi immersed himself in the data, adding and fine-tuning metrics that would allow him to better convey eBay’s message.Before joining Flywire as CFO, Pitigoi spent two decades rotating through leadership roles at eBay and PayPal, building his finance acumen across treasury, investor relations, FP&A, and data analytics. “I never stayed in a single role for more than 18 months,” Pitigoi tells us, describing his drive to learn every facet of the business. By immersing himself in diverse functions, he honed both analytical and communication skills—critical for strategic decision-making.At eBay, the lack of comprehensive data became a new language barrier, prompting Pitigoi to advocate for stronger data architecture. “Numbers alone can’t tell a story unless they’re accurate and well-organized,” he tells us, underscoring his belief that precise, actionable information fuels effective narratives. This mindset ultimately shaped his approach to finance leadership: be as fluent in data as in interpersonal communication.Today, at Flywire, Pitigoi champions the idea that true value emerges when finance guides broader organizational goals. His journey from struggling to speak English in Cape Town to optimizing data-driven storytelling at a global fintech highlights a simple truth: conquering communication obstacles—whether linguistic or numeric—can spark remarkable career transformation.

Stacy Tumarkin, CFO of KubeCost, shares her journey as 'The Accidental CFO,' stepping into leadership roles unexpectedly. She discusses the challenges of imposter syndrome and how embracing discomfort fueled her growth. Tumarkin highlights the significance of adaptability in startup environments and how her diverse experiences shaped her strategic approach. She also emphasizes the vital role of leadership over numbers, blending her passion for finance with a people-first mentality. Additionally, her transformative leap into yoga teacher training showcases her unique perspective on balance in leadership.

Back in the mid 1990s–when Russ Keefe decided it was time for a career pivot–he got behind the wheel. With a Jeep packed full of his belongings, he drove from Washington, D.C., to San Francisco, father riding shotgun, to explore fresh opportunities in Silicon Valley. He had just completed a stint at the U.S. Securities and Exchange Commission, where he gained a deep respect for transparency and learned the importance of full disclosure.Eager to drive business outcomes, Keefe immersed himself in tech, soon discovering a passion for FP&A and leadership. Early roles exposed him to sales operations, giving him a front-row seat to understand revenue streams and product strategies. “That was when I realized finance is so much more than keeping score—it’s about guiding strategic decisions,” Keefe tells us.Today, as CFO of cybersecurity innovator Corelight, Keefe applies a forward-looking mindset to navigate hypergrowth markets. His background at the SEC informs his ethos of communicating frequently and candidly with stakeholders. Meanwhile, his operational experience shapes his focus on customer satisfaction, product differentiation, and consistent value delivery.Keefe tells us Corelight’s Net Promoter Score sits in the mid-60s, underscoring the company’s commitment to serving high-stakes clients in government, finance, and critical infrastructure. He believes finance leaders should be business people first—professionals who leverage financial expertise to power innovation and adaptability. His journey—beginning with a cross-country leap of faith—demonstrates that calculated risks, paired with diligent career building and leadership insight can yield results.

It was shortly after Eugene Wong exited the banking world to advance into a senior operations role that he realized the importance of a holistic view. At one meeting, he uncovered a disconnect between product and sales teams that threatened a strategic initiative. By stepping in and aligning priorities, he emerged as a “quarterback,” bridging perspectives and clarifying responsibilities.This revelation set the tone for Wong’s career journey. Originally honing his financial acumen at Silicon Valley Bank, he gained close exposure to startup ecosystems and leveraged finance transactions. Later, he pursued an MBA, joined Goldman Sachs to build on transactional capabilities, and returned to Silicon Valley Bank in a senior role. Ultimately, he stepped into the fast-paced realm of growth-stage companies, seeking to become a true financial operator.Today, Wong serves as CFO of Clara Analytics, where he orchestrates data-driven decision-making and fosters cross-functional collaboration. “You can’t stay behind spreadsheets,” Wong tells us, “you have to understand what each team does day in and day out.” By meeting regularly with department leads, he seeks to position finance as a trusted partner rather than a distant overseer.Wong credits his “big-picture” focus for sharpening his resource allocation. “Anytime you spend money or time in one place,” Wong tells us, “you’re making a bet you can’t place elsewhere.”