Inside the world of retail businesses, Greg Wookey’s CFO career has advanced down a path that parallels the sector’s growing appetite for more sophisticated software. Such was the case roughly 10 years ago, when he stepped into the CFO office at Mindbody—a firm whose well-known software helped fitness centers across the country to manage the demands of their clientele—and such is the case today, as Wookey serves as CFO of Boulevard, a SaaS developer whose offerings are specially tailored to high-end salons and spas. This arena—in what Boulevard and other software developers commonly refer to as “appointment-based retail”—is where Boulevard now hopes to help salon and spa owners to achieve a more sophisticated and aesthetically pleasing customer booking experience. “We saw that there was an inability of salon owners to connect effectively with their clientele, so this was about making booking appointments and integrating payments easier so that salon owners could accept payments more easily,” says Wookey. Meanwhile, Wookey is keeping a close eye on Boulevard’s own customer engagement activities. “We actually have very good metrics in terms of the size of our pipeline, the pipeline velocity, and how fast the opportunities are moving through that pipeline. Then we measure the direct marketing spend that we have and how that relates to new business,” the finance leader explains. –Jack Sweeney CFOTL: Tell us about a finance strategic moment. Wookey: One that comes to mind was back in 2009, when I started at a company called Mindbody. We were a little bit bigger than Boulevard is now and we were a few rounds of investing ahead of where we are at Boulevard, but it was very clear that the business was growing extremely fast and that there was the potential that at some point in the future we might be able to become a public company. With this in mind, I knew that there were certain things that we needed to do at Mindbody to prepare for that moment--which didn't come until six years later. But in the time that I was heading finance there, what I tried to do was lay the foundation for what would be the ability to go public at some point in the future. This really involved several things. One was to build out a more robust internal team in terms of accounting and finances and FP&A. Another was to create the ability to use tools that would be more supportive of a public company--for example, moving off of QuickBooks and onto NetSuite so that our reporting would be stronger. We also changed relationships in terms of our audit, banking, and legal. These were all things that I set in motion very early on in my career there. This eventually proved to be something that was important for the ability of the company to go public, which we did in 2015. This was a moment when I looked at the finance operation, looked at what the state of it was at the time, and then thought about where it needed to be several years down the road. You have to start these processes in motion and not wait too long, or suddenly you're up against it in terms of timing. This was a very strategic thing that I did in terms of trying to make sure that the company was prepared in case this happened, which it eventually did, and it goes well beyond finance. It touches the entire company in terms of how we operate, what processes we put in place, how we access data, things of that nature. For me, this was probably the most significant strategic initiative that I embarked on that started from finance and really ended up impacting the entire company.