Where amazing partnerships begin


Trailhead Media is an all-new out of home media company with a growing network of printed and digital billboards in attractive advertising markets across America. We are customer-focused and quality-obsessed, and unlike any other media company you may have worked with in the past. 


We are passionate about:


Being small business expert

by helping local organizations solve problems, attract and retain more customers and become better marketers.


Working smarter and reducing complexity

by making billboards easier to plan, buy and use.


Collaborating closely 

and treating customers the way they’d like to be treated – as true, long-term partners.


Becoming a force for good

and an integral part of the local communities where we operate.

Our growth story

Trailhead Media was founded in 2020 by Robert Macmillan with the acquisition of the outdoor advertising assets of Busby Outdoor in Mississippi and Louisiana. This was followed shortly thereafter by deals with Cox Media, Spartan Outdoor Advertising, Leslie Outdoor, InSite MediaCom and BPS Outdoor Advertising. In 2021, Trailhead expanded its network again by acquiring additional outdoor advertising assets from media operators Dusty’s Outdoor, Wingate Outdoor, Action Outdoor, and Southern Billboards. 

While our growth story has currently been focused on the southeastern United States, our ambition is national. We will continue to expand our network by identifying, acquiring, and operating well-run out of home media companies in attractive local markets from coast to coast. 

Trailhead Media may be a brand-new company, but our legacy is substantial. Every company that we’ve integrated into the Trailhead family has brought its own talented people, practices and customer relationships, adding to our culture and strengthening our DNA. Honoring the past while leaning into our vision for the future, Trailhead Media will build on this legacy by exploring new ideas, trying new things, embracing new technologies, and delivering a flawless product. 

We are committed to delivering the perfect outdoor media canvas to our clients, while helping them become better marketers. This is what defines us as a company, because we know that when our customers succeed, we succeed.  

Trailhead Media is a proud member of the Out of Home Advertising Association of America (OAAA) and Geopath. The company is headquartered in Laurel, Mississippi.

We stand for:



The foundation for everything we do.



The #1 factor that makes our medium so effective.


Long-Term Relationships

We are dedicated to building our customers’ business. When they succeed, we succeed.


Quantifiable Results 

We are ROI and metrics driven, and we believe in measuring success. The numbers don’t lie.

Our commitment to quality.

In out of home advertising, the medium is the message. We are fanatical about quality products, quality maintenance, and quality business processes. In fact, over the next two years Trailhead Media will spend over $10.4 million on quality initiatives like expanding our network, upgrading our inventory, improving lighting, and converting printed billboards to digital. 

Our investments include: 


In digital billboard upgrades, new control technology, and digital conversions.


To upgrade billboard structures, including painting, high efficiency LED lighting, safety equipment, aprons, and insignia.

$800 K

To develop three new locations in high demand markets.