Nearly 20 years later, CFO Trent York tells us that he can still hear the finance executive’s exact words. “Trent, I don’t need you tell me how not to do something—I need you to help me to figure out how to work through the issue and what needs to be addressed in order for us to be able to expand,” recalls York, placing just enough emphasis on the word “not” to expose a degree of anxiety that still lingers. At the time, York was a newbie controller for Golfsmith, an Austin, TX–based golf specialty retailer that in the 2000s was opening dozens of stores annually as golf enjoyed newfound popularity nationally amidst the Tiger Woods boom.  “We went from 20 retail stores at the time I joined to close to 80, and we actually took it public, so this was really a build-and-scale moment that was quite exciting,” explains York, who advanced into the vice president of finance role as the golf retailer began to prepare for a public offering that ultimately debuted on NASDAQ (symbol: GOLF) in June 2006. Beyond gainful employment and resume enrichment, Golfsmith provided York with a series of “build-and-scale” moments of insight that allowed him to confidently step into yet another fast-growing Austin phenom of the 2000s, HomeAway. “HomeAway was about scale. There was meaningful organic growth, and we were very acquisitive along the way, too, because the market that we were looking to bring together was fragmented,” remembers York, who would spend 13 years at the company and enter the CFO office a year after its sale to Expedia Group in 2015. Later, HomeAway was rebranded as part of VRBO. “Following the sale, we pivoted our entire business model from being subscription-based to being transaction-driven, which was really more aligned with the marketplace—and to pivot like this was not an easy thing to do,” reports York, who adds that his lesson or takeaway from “the pivot” was coming to understand how making complex tasks simple could help an organization to achieve greater agility.   Says York: “The ability to be agile or stay fluid within a changing environment—and to drive through it—comes back to keeping things simple.” –Jack Sweeney   Leave rating & review   Signup for our Newsletter GET MORE: Order now The CFO Yearbook, 2021