Matthew Novick traces one of his earliest business lessons not to a boardroom, but to a furniture store in Portland, Maine. Growing up in his family’s business, he learned how to read credit reports, price products, and assess who was “credit worthy,” skills that showed him how decisions affect a business long before he ever closed a set of books, Novick tells us.

That operational grounding followed him into finance. Early roles at IBM and AOL put him on both the expense and revenue sides of the P&L, including sales operations and compensation design. Those experiences shaped his belief that finance is not just about counting dollars, but understanding what the numbers actually mean, he tells us. “If you don’t understand what goes into closing those books… you’re never actually going to understand your business,” he says.

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His path accelerated quickly. After leaving AOL, Novick joined Magnetic, where he became VP of Finance and then the company’s first CFO in his early 30s. Since then, he has moved through multiple CFO chapters across ad tech and data-driven businesses, refining how he partners with CEOs. That partnership, he explains, is central—so central that he once flew across the country to spend two days with a CEO before accepting a role, Novick tells us.

A defining strategic moment came at PlaceIQ, when the company received an unexpected inbound acquisition inquiry. Preparing to assess synergies, unit economics, and whether “one plus one really equals three” reshaped how he thinks about strategy and readiness, Novick tells us. Today, as CFO of TripleLift, that mindset carries forward—pairing operational fluency with disciplined decision-making in an increasingly complex, AI-influenced finance landscape.