At the 2026 OOH Mediacon OAAA CEO Anna Bager conducted a wide-ranging interview with Ross Reilly, the newly appointed President of Lamar Advertising’s Outdoor Division. Here are some excerpts, sponsored and analyzed by SignValue. We hear that 8 of the 14 direct reports of Sean Reilly now report directly to Ross. Looks like Ross Reilly is being groomed to be the next Lamar CEO.
Ross Reilly’s background
I’m based in Baton Rouge, Louisiana, and got into this industry there about 12 years ago. I fell in love with how deeply rooted this business is in communities — whether it’s the State Fair, partnerships with municipalities, or just being embedded in the life of a city. I served as general manager of the Baton Rouge plant, which is really where I got into the sales side of the business. The GM role is fundamentally about managing the revenue and expense side of a local plant, and that ground-level experience has shaped everything since. For the past five years I’ve been focused on capital allocation — we’ve done billions of dollars in asset purchases and some creative financing and investing in adjacent spaces. And now I’m president. I have to be honest — it doesn’t hurt that my last name is Reilly and my middle name is Lamar. I’m the fifth generation of my family to work at Lamar Advertising.
Reilly likes murals
In my career I’ve had the chance to work on a lot of things I’m passionate about — programmatic, capital allocation, partnerships — but acquiring Colossal Media has been one of the biggest growth experiences for me personally. It’s a really, really hard business. Managing highly skilled painters, the ideation-to-execution process, getting our accounting team comfortable with a completely different revenue model, the physical logistics of large-format painted walls in Brooklyn and Manhattan — it is genuinely demanding work. There’s a reason not many people are doing it.
What I find extremely rewarding is watching agencies and brands engage with it. They’re used to optimizing everything — measuring every impression — but with a mural, there’s a moment where they just let themselves enjoy it. It becomes experiential. The act of painting a mural is itself an event. People watch it go up. It gets shared on social media before it’s even finished. That organic engagement is hard to replicate.
I also think it was a business challenge Sean intentionally handed me. He probably figured I wouldn’t want to touch it — and then said, “you know, we should do this.” Part of the appeal is going back to our roots. When you’ve been around for 125 years, some of the guys I used to manage as a GM were originally painters — they were doing for my father what our Colossal crews are doing today. There’s something meaningful about keeping that craft alive and vibrant.
And it speaks to something broader: our industry and our people can hold two truths in their heads at the same time. We can pursue rigorous data and measurement efficiency, and we can be deeply, unapologetically creative. Those things are not in conflict.
A use for AI at Lamar
One concrete application I’m excited about: we have over 25,000 leases, each secured by a legal contract that’s often 20-plus pages long and completely unique in its terms and nuances. There could be enormous value in using AI to summarize and quickly surface information from those contracts — so we can ensure compliance, reduce friction, and better understand where our operational pressure points are. That’s a real estate and legal application that goes right to the core of how this business works, and I think it’s one of the more interesting places we can go.
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