Hi, I’m Kevin Ross—tech enthusiast, digital builder, and the unofficial IT support for my friends and family. Growing up in Fairfield County, CT, I got my first computer from my dad. What started as a way to keep me busy turned into a full-on obsession with creating, building, and figuring things out online.
In college, I co-launched a lifestyle blog with Jason Olephant called University Primetime that grew into the third-largest in its category, surpassing Barstool Sports in traffic and revenue. We pulled in over $1 million in revenue and over 100 million visitors, which I’m still trying to wrap my head around. I handled the website, marketing, and a lot of other stuff that companies usually hire entire teams for.
After that, I joined Atlantic Records, which was as exciting as it sounds. I helped create digital campaigns for big-name artists and got really good at pretending I wasn’t starstruck. Working with the Urban Marketing team taught me how to turn creative chaos into strategic campaigns that actually worked.
At Obi, I had the time of my life leading growth and product for a company that quickly became the world’s largest rideshare aggregator. Naturally, this didn’t sit well with Uber and Lyft, who were constantly looking for ways to shut us down. The drama made the work even more exciting—I led the design for the app, launched features like Fare Prediction™, and crafted marketing strategies that brought in more users while keeping them engaged. It was a chaotic, high-stakes environment, but I thrived on the challenge of building something that genuinely disrupted an industry.
Now, I’ve stepped into aviation—a field I’ve learned is only slightly less regulated than the nuclear industry (yes, really). As Chief Digital Officer at Flight Club, I’m wearing many hats. One minute, I’m writing detailed feature specs for our booking platform; the next, I’m troubleshooting why a team member’s emails won’t send. It’s been a crash course in adaptability, but leading all things digital—designing apps, managing platforms, and creating materials for fundraising—has been incredibly rewarding.
Whether it’s scaling platforms like University Primetime, driving growth at Obi, or shaping the future of Flight Club, I’m passionate about combining technology, design, and strategy to create impactful digital experiences.
Pssst…You can drag the photographs