On Mount Hood, Scott Cutler once found himself in a whiteout with a spoon. He used it to dig a snow cave. Years later, discussing the episode, he offered a suitably practical explanation: “I’m here today because I just dug in and worked the problem.” In a career full of transactions, it is a memorable example of making do with the equipment at hand. A spoon has its limitations. So, presumably, does waiting for better equipment.
Cutler is now President and Chief Executive Officer of HealthEquity, based in Utah. His route there runs through securities law, investment banking, the New York Stock Exchange, StubHub, eBay and StockX. It is a career that can look scattered until you notice how often he has worked around the same question: what makes people comfortable enough to enter a market and make a trade?
There is a personal question running alongside it. How does someone trained to get a transaction done learn to run an organization full of people who need more than the next transaction? Cutler has been unusually willing to talk about the adjustments. The professional story moves through different kinds of listings. The human story involves learning how to stay present after the deal.
A ticket is a kind of promise
Cutler studied economics at Brigham Young University and earned a law degree at the University of California, Hastings College of the Law. His early work as a corporate securities lawyer gave way to technology investment banking. In April 2006, he joined NYSE Euronext; he would spend nine years there as an executive vice president. By April 2015, he was moving into a very different kind of exchange: StubHub.
Consider the change of scenery. A corporate listing and a ticket to a ballgame carry different expectations, different rules and different consequences when something goes wrong. Yet both require an organization to coordinate participants who arrive with their own interests. An exchange has to earn its place between them. Seen that way, Cutler’s move from Wall Street to ticketing becomes easier to follow.
At StubHub, he initially oversaw a team of about 800 people working across the United States, Europe and China. The job involved extending an existing marketplace: improving the experience for buyers and sellers, developing partnerships and pursuing international opportunity. The attraction was in the operation itself. He had come from a business in which the community, the platform and the transactions were intimately connected.
A wider map brought more partners, customers and operational demands.
During his presidency, StubHub’s presence expanded from four to more than 48 countries. His later eBay biography also recorded two acquisitions and partnerships across sports and music. The figures describe a business becoming more geographically complicated. They also explain why an executive with experience managing relationships across a large marketplace might be useful in a company selling access to an evening out.
In August 2017, eBay promoted him to Senior Vice President, Americas. The announcement kept him at StubHub while a successor was sought. His new remit covered a broader marketplace business, and his responsibilities eventually included marketing, merchandising, operations, shipping, payments and risk. That list is a useful corrective to the idea that commerce begins and ends with finding an appealing product. Someone must make the machinery behave.
The shoes come with a balance sheet
StockX made the relationship between product and market particularly visible. Buyers and sellers could trade sought-after goods using pricing information generated by the marketplace. Cutler became CEO in June 2019, succeeding co-founder Josh Luber. He had already been an investor and advisor. He was joining an enterprise he knew, with a business model that gave his exchange experience an unusually literal second life.
The appointment arrived with a $110 million funding round and a valuation above $1 billion. At that point, StockX already reported customers in nearly 200 countries and more than 15 million monthly active users. Those were the starting conditions, rather than achievements to assign to an incoming chief executive. The challenge was to operate and develop a marketplace whose reach already exceeded the scale its age might suggest.
By April 2021, StockX announced financing at a $3.8 billion valuation. The transaction combined a $195 million secondary tender offer with $60 million of new primary shares. The distinction matters: a headline financing number can include money paid for existing holdings as well as fresh capital for a company. StockX also reported more than $400 million in revenue for 2020. Sneakers had acquired a substantial set of financial footnotes.
There was still culture to understand. Cutler has described senior candidates at StockX losing credibility when their footwear suggested little interest in the business. A polished background could get someone considered. It could not automatically supply an understanding of sneaker enthusiasts. The test was pointed, perhaps uncomfortably so. In this workplace, the interview began a little closer to the floor.
The customer speaks another language
Cutler’s explanation of international expansion was refreshingly concrete. Customers wanted to read in their own language, use local payment methods and speak to someone who understood them when a problem arose. Delivering a consistent experience meant investing in those details. A site could be visible around the world while still making a purchase feel foreign to the person attempting it.
That distinction helps explain the operational side of his career. The recurring business problem is access: who can participate, what they understand about the transaction and how much effort the system demands. For a customer, the meaningful measure of expansion may be something as ordinary as a successful checkout. Corporate geography is easier to celebrate than payment compatibility. The latter tends to matter more at the decisive moment.
In September 2024, Cutler was explaining another route to access: StockX’s relationship with Walmart’s online marketplace. The idea was to put products in front of customers who might encounter them through a different shopping destination. In his discussion of the arrangement, he emphasized exposure to Walmart’s customer base and StockX’s emphasis on verification. The new doorway mattered alongside the goods behind it.
He also described a customer base in which 60 percent were under 35. That figure gives context to the cultural attention. The company was serving people whose tastes could move rapidly, while trying to make the buying process dependable. Fashion supplies novelty. A marketplace must also supply enough consistency for someone to return. Running the business means living with both demands at once.
Learning to stay in the room
Cutler’s descriptions of leadership have become more personal than a discussion of market mechanics. In 2024, he spoke about becoming more empathetic and less transactional. Personal check-ins and meetings with the whole company every two weeks were among the practices he described. He described accessibility and transparency as especially important to a business expanding internationally. The emphasis puts a human obligation inside a story usually told through expansion figures.
“Being accessible and transparent has been really important as we’ve expanded globally.”
Scott Cutler
His account of his upbringing adds another dimension. Born in California and raised in Seattle, he grew up among six children and delivered newspapers when he was young. He has connected that daily responsibility to his enduring habit of rising early. His father helped make the outdoors part of family life; his mother kept a reminder about persistence on the refrigerator. The childhood he describes had a regular delivery schedule and fairly high expectations.
The outdoors remained part of adulthood. He has crossed the Alps on skis, run more than a dozen marathons and ridden Tour de France stages as a spectator. His eBay biography contains another detail with excellent corporate timing: he recalled beating former World Cup racer Phil Mahre in a televised amateur race on skis bought through eBay. Even a hobby, apparently, could produce a customer testimonial.
These episodes make him easier to picture beyond a corporate photograph. They also invite a little restraint. A ski race has a finish line; an organization keeps asking questions the following morning. What is interesting in Cutler’s account is the combination of competitive appetite and a stated willingness to change his approach to other people. The lessons require different kinds of practice.
The next seat, closer to home
In November 2024, StockX announced that Cutler would step down at year-end and co-founder Greg Schwartz would become CEO on January 1. Cutler would return to advising. The company described preparing the business to become founder-led again as part of his remit. His tenure thus included the work of handing over the operation. The successor had been his partner in running it.
On January 6, 2025, Cutler became President, CEO and a director of HealthEquity, succeeding Jon Kessler. His current responsibilities also include an independent directorship at Brookfield Asset Management. The institutional setting has changed again. The career now places a former securities lawyer and sneaker-marketplace executive in the leadership of a Utah-based public company, with another boardroom connecting him to the wider financial world.
There is a local sporting connection, too. In June 2026, HealthEquity announced that it would become the jersey patch partner of the Utah Jazz and Salt Lake City Stars beginning with the 2026-27 season. The agreement also included youth basketball, scholarship and literacy initiatives. Cutler welcomed the connection to the community the company calls home. After the exchanges, tickets and sneakers, basketball offered another familiar point of contact.
Across the changes, his story keeps returning to participation. People need a reason to enter a marketplace, a workable way to transact and confidence in the organization in between. Colleagues need access to the person running it. Cutler has spent years discussing both. The next chapter will be judged in the ordinary encounters that follow an appointment: the purchase that works, the question that gets answered, the conversation a leader makes time to have.