About this episode
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