Business Hours
Monday 8:00am - 5:00pm
Tuesday 8:00am - 5:00pm
Wednesday 8:00am - 5:00pm
Thursday 8:00am - 5:00pm
Friday 8:00am - 5:00pm
Saturday Closed
Sunday Closed
Listed In: Advertising Agencies
Trailhead Media is a fast-growing outdoor advertising company established in 2020 through the acquisition of Busby Outdoor’s billboard assets in Mississippi and Louisiana. Since its founding, the company has pursued a strategic expansion plan focused on acquiring established outdoor advertising… Trailhead Media is a fast-growing outdoor advertising company established in 2020 through the acquisition of Busby Outdoor’s billboard assets in Mississippi and Louisiana. Since its founding, the company has pursued a strategic expansion plan focused on acquiring established outdoor advertising operators and strengthening its regional presence across key markets. Shortly after its initial acquisition, Trailhead Media expanded by acquiring assets from well-known operators including Cox Media, Spartan Outdoor Advertising, Leslie Outdoor, InSite MediaCom, and BPS Outdoor Advertising. This momentum continued throughout the following years, with 16 additional acquisitions completed in 2021, followed by 7 more in 2022 and 13 in 2023. With further acquisitions finalized in 2024, the company has successfully completed a total of 44 acquisitions in just a few years. Through this steady growth strategy, Trailhead Media has built a strong and diversified portfolio of outdoor advertising assets. The company focuses on maintaining quality billboard locations, strengthening partnerships, and providing reliable advertising opportunities for businesses seeking effective out-of-home marketing solutions. By combining operational expertise with strategic market expansion, Trailhead Media continues to establish itself as a leading presence in the regional outdoor advertising industry. Read more
By Mick Hunt on May 19, 2026 Verified by Google
I've worked with a lot of teams over the years. None of them moved like Trailhead Media. Concept to contract to a live billboard, and every step felt like they were inside my head. They didn't just take an order. They understood the brand, the audience, and the moment. My visibility today is a direct result of their work. Hands down the best customer experience I've ever had.
By Jacob Landis on August 14, 2025 Verified by Google
Mrs. Graham and Mr. Hart have been FANTASTIC to work with on our billboards! They are super fast in responding to emails and will help bring any idea you have to life! Highly recommend them for all of your billboard needs!!
By Danny Perez on July 29, 2025 Verified by Google
I’ve been working with Trailhead Media for almost two years now, and the experience has been amazing. From the beginning, Julie Griffin has gone above and beyond to help me grow my business through billboard advertising.
She made sure I was happy with the design, gave helpful advice on how to stand out, and has always been patient and supportive. I recently added digital billboards too, and once again, Julie made the process easy and smooth.
She’s not just a great sales executive—she’s a great person, and it shows in everything she does. The print quality is great, turnaround is quick, and the results have absolutely made a difference in my business. I’ll definitely keep working with them!
By Lauran Stephens on April 30, 2025 Verified by Google
When the salon I manage began to consider billboard advertising I knew exactly who to contact. Bobby Hart’s reputation preceded him and we were not disappointed. As soon as I reached out he visited the salon, answered all our questions, gave us several location options for our billboard and continues to check in with us.
If you’re considering billboard advertising (which by the way has brought a lot of business our way) definitely give Bobby a call you won’t be disappointed.
By Kyle Cullars on April 27, 2025 Verified by Google
Awesome company to work with for your advertising needs! They are super responsive, provide great artwork service for developing beautiful ads that get attention, and my contact there - Matt Cobb - is awesome! He does outstanding work while providing the perfect combination of reaching out periodically to encourage more advertising while not being too pushy! Give Matt and Trailhead Media a try - you'll be glad you did!
By Taylor Hembree on April 15, 2025 Verified by Google
I work with them to get our shows advertised for the theater that I work for! Matt makes it super easy to get those signs up in a timely manner. Payment processing is easy and the whole process is just so simple! We definitely see a return on our investment with the billboard placements that we use!
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