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.
Read MoreLee’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 environment where strategic insights drive company-wide innovation.
“Be a businessperson first. That principle has always encouraged me to operate as a strategic thought partner with a financial toolkit to solve problems. I still love spending time in the data, but it’s always in the context of the broader business strategy and customer impact.” —Jason Lee, CFO, Faire
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CFOTL: Tell us about Faire. What type of company is it, and what are its offerings?
Lee: So (let’s) talk about Faire. I just came back from (an) investor conference, and whenever I talk about it, I get fired up. What is Faire? It’s a wholesale platform that connects retailers—people who sell things—with brands—people who make things—and ultimately helps retailers discover and find the right products to sell to their consumers.
Imagine your favorite retail shop—your local neighborhood bookstore, home store, or toy shop. They stock hundreds, if not thousands, of items. Each item goes through a wholesale relationship where you negotiate minimum orders, shipping, payment terms, and so on. There’s a lot of complexity in managing all that. But if you think about what really matters to a retailer—and why you, as a consumer, go there—it’s that they have great products and a great assortment. We help with that number-one job: finding great products that sell.
Read MoreWe help retailers in three ways. First, we offer a marketplace of hundreds of thousands of retailers and 100,000 brands—so in a fragmented market, we help them find that ‘diamond in the rough.’ Second, we tackle workflow complexity (like) POs and invoices by automating those processes, so you just order and go. Third, because we aggregate retailers and brands, we can negotiate better shipping and payment terms. Not every smaller retailer gets access to terms like a big-box retailer does, but we (ensure) they get the best possible prices.
When you put all of that together, it creates a really rich value proposition that helps these retailers succeed. The last point I’ll make is that the incumbent wholesale experience is still incredibly challenging, fragmented, and manual—where consumer e-commerce was 10 or 20 years ago. The things we take for granted as consumers (on) Amazon or other sites simply aren’t there in wholesale. We’re driving that transformation.
Faire | www.faire.com | San Francisco, CA