The Trailhead Model Looked Simple on Paper. Building It Was Not.
What a press release calling it “simple” leaves out about actually building it.
TRAILHEAD MEDIA · CEO PERSPECTIVE
The way Trailhead Media describes itself in a press release is simple: acquire fragmented rural billboard operators and run them through a fully remote, contractor-based platform. CEO John Murrow is the first to admit that description, while accurate, doesn’t capture what it actually took to build.
Every Market Is Its Own Market
One assumption that got tested early: that a contractor network built in one state would translate cleanly to the next. It didn’t. Murrow has written that the right local partnerships in the Upstate of South Carolina didn’t automatically solve anything in north Georgia — every new market meant building real relationships from scratch.
Systems Built to Be Rebuilt
Trailhead’s internal reporting infrastructure has been rebuilt four times in five years, each time a new threshold of scale outgrew the last system. Rather than waiting for something to break, the team learned to ship fast and rebuild on schedule.
“The model is a thesis. The execution is a discipline. The gap between them is the company.”
Murrow has also written about the moment he stepped back from reviewing every deal personally in 2022 — a hard shift after two years of being the relationship in nearly every room, but one he says made the team sharper and the company bigger than any one person — a milestone in the story told on Trailhead’s About page.
Read more on how customer-facing execution shaped Trailhead’s culture in What Out-of-Home Advertising Still Gets Wrong About Customers.
Read the full story from Trailhead’s CEO: “The Trailhead Model Was Simple. The Execution Was Not.” on johnmurrow.com.