From startup CFO to boardroom strategist: A fireside chat with Jimmy Orsillo

From the 2025 Technology Finance Symposium - East

This session’s fireside chat with Jimmy Orsillo, General Partner and CFO at Underscore VC, moderated by Michelle Kupka of Baker Tilly, explored the evolution of the CFO role from early career experiences to boardroom strategy, with a particular focus on startups and venture-backed companies

Orsillo shared that his interest in finance was sparked early, growing up with a father who served as a controller and later CFO. This early exposure to the financial management of a business, combined with hands-on experience managing estate accounting as a teenager, cultivated his fascination with turning numbers into actionable insights and stories. He pursued this interest academically at Boston College and then built practical experience that eventually led him into CFO roles, first in public companies and later in venture-backed startups.

Orsillo reflected on the transition into his first CFO role, noting that he initially experienced impostor syndrome and the challenge of assuming full responsibility for a business. Over time, he learned to command authority over all aspects of operations, a skill that later translated into his effectiveness in boardroom settings. He emphasized that having been an operator and a CFO gives him a high degree of empathy and credibility when advising companies at the board level. For him, the boardroom is not only about governance and compliance but also about problem-solving, helping leadership teams navigate operational challenges and shaping the strategic direction of the business.

Discussing the evolution of the CFO role, Orsillo highlighted three dimensions: the office of the CFO, which focuses on reporting, metrics and data management; the officer role, which entails formal fiduciary responsibilities; and the operator role, which has grown significantly, particularly in startups where CFOs must optimize capital allocation, pricing, gross margins and go-to-market strategies. He stressed that the operator aspect has become increasingly critical as the bar for public market readiness has risen dramatically, requiring CFOs to identify friction points and unlock value across the business.

Orsillo also provided a venture capital perspective on current market dynamics, noting a divergence across seed, middle-market and late-stage companies, with valuations, capital availability and growth expectations varying widely. He advised startup founders to either pursue hypergrowth or focus on disciplined cash management while cultivating early relationships with investors and considering potential exits through M&A or secondary markets, given the slowdown in IPOs. He highlighted vertical AI, digital transformation and sovereign AI as key areas of technological innovation that will drive the next wave of growth and value creation.