Every month, OAAA’s marketing team sits down with an industry leader to discuss the latest insights, trends, and best practices for the OOH industry.
Read John’s Q&A in The Drum.
What excites you about OOH right now?
What excites me most is that OOH is getting smarter without losing what has always made it work. You can’t skip a billboard, block it, or scroll past it. Now we’re adding digital, programmatic buying, and better data on top of that, so advertisers keep the reach they’ve always counted on and gain flexibility and accountability. At Trailhead, we operate about 3,250 faces across nine southeastern states, including 305 digital displays. Digital lets a local business change its message by the week, the day, or the hour. On the operations side, AI is helping a lean, remote team serve local advertisers at a level that wasn’t possible a few years ago.
What message do you have for brands that haven’t bought OOH before?
Think about your customer’s daily drive. Every day they pass the same roads on the way to work, school, church, and the grocery store. OOH puts your name in front of them over and over, and that repetition builds familiarity and trust. You don’t need a national budget to make an impact. A good example is a new RV dealership we started working with about four months ago. Customers have told them they found the dealership through its digital billboards and didn’t even know it was in the area, and those customers are turning into buyers. That’s what OOH does best: it puts a local business on the map for the people who drive past it every day.
What’s the next big thing for OOH?
Three things are converging: programmatic and data-driven buying, post-campaign attribution and measurement, and AI. Together they’re making OOH easier to buy, easier to prove, and more efficient to run. We’ll see more automated buying, and that’s a good thing. But I don’t think automation replaces the relationship. Technology handles the transaction. People still have to understand a client’s business and help them win.
How is local OOH evolving, and where are the biggest growth opportunities?
Local is still the heart of this business, and I expect it to stay that way. What’s changing is what local advertisers can do. With digital and programmatic tools, small businesses can now run flexible, measurable campaigns that used to be out of reach. The biggest opportunity is helping local companies grow their businesses. I’ve always believed that if we help enough clients get what they need, we’ll get what we need. That starts with building great teams: people who know their markets, care about their clients, and have the tools to spend more time with customers and less time on paperwork. That’s where AI earns its keep for us.
Published: October 29, 2026