Every billboard company has a founding story, and for Trailhead Media, one of the first chapters was written in Easley, South Carolina, by a man who had already spent nearly three decades building relationships in the out-of-home industry: Kerry Cox.
A Career Built in Out-of-Home Advertising
Kerry Cox began his career in out-of-home advertising in 1991, spending years with Naegele/Fairway before serving as the company’s Corporate Sales Development Director from 2013 to 2015. That experience — understanding markets, building relationships with local advertisers, and knowing what makes a billboard location work — became the foundation for his own company.
Founding Cox Media
In 2015, Cox struck out on his own and founded Cox Media, building a network of digital and static billboards centered in Easley, South Carolina, just outside Greenville. Over the following five years, Cox Media grew into a respected presence in the local out-of-home market, serving advertisers across the Upstate region.
Joining Trailhead Media
In July 2020, as part of Trailhead Media’s founding wave of acquisitions, Cox Media’s digital and static billboards became part of the growing Trailhead network. At the time, Cox and his wife, Julia, were looking ahead to retirement and more time with family — but Kerry’s story with Trailhead didn’t end there.
A Legacy That Continues
Today, Kerry Cox serves as Director of M&A at Trailhead Media — helping guide the very kind of acquisitions that first brought his own company into the fold. It’s a fitting continuation for someone who spent his career building relationships in Southeast out-of-home advertising, and it’s part of why Trailhead’s growth has always been about more than just buying billboards: it’s about bringing in the people who understand the markets best.
Cox Media’s structures remain part of Trailhead Media’s South Carolina billboard network today, serving advertisers in the same Upstate communities Kerry Cox built relationships with over more than three decades in the business.
Read more about the Greenwood market today: Billboard Advertising in Greenwood, South Carolina.
Source: Billboard Insider
