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About

Trailhead Media.

About

Trailhead Media.

Where Amazing Partnerships Begin.


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

Our Growth Story.


Trailhead Media was founded in 2020 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, we continued to expand our footprint by acquiring the assets of 16 more operators. That was followed by 7 acquisitions in 2022 and 13 more in 2023. With two more in 2024, we have completed 44 acquisitions.

 
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 has a substantial legacy. 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.

Our Passion.


Being The Small Business Expert

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

A black and white drawing of a person 's head with a brain in it.

Working Smarter and Reducing Complexity

by making billboards easier to plan, buy and use.

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Collaborating Closely 

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

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Becoming a Force For Good

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

A black and white drawing of a person 's head with a brain in it.
A black and white drawing of two people shaking hands.
A white background with a few lines on it

Being The 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 Mission.


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Innovation

We continually adapt and evolve, embracing new technologies and methods to stay at the forefront of the advertising industry.

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Integrity

We operate with honesty and transparency, building trust with our clients through consistent, reliable service.

A black and white drawing of a cross on a white background.

Impact

We strive to make a significant difference in the success of our clients' businesses, delivering results that matter.

A black and white silhouette of a team on a white background.

Inclusivity

We respect and value diversity, ensuring our services reach a wide and diverse audience.

Our Commitment.


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 $20 million on quality initiatives like expanding our network, upgrading our inventory, improving lighting, and converting printed billboards to digital. 

Our Investments.


$6.9 MILLION

spent on digital conversions and new builds.

$4.0 MILLION

invested in upgrading billboard structures and asset enhancements

37%

of digital faces have been replaced, upgraded, and had tech improvements at a cost of $4.8 Million

Meet the Team!


At Trailhead Media, we believe in the power of creativity, collaboration, and innovation. Our dedicated team is comprised of passionate individuals who bring a diverse range of skills and expertise to the table. Together, we strive to deliver exceptional media solutions that not only meet but exceed the expectations of our clients.

Our Team
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