Our Team

Larry Lipscomb

Managing Member

As a third generation Springfieldian in outdoor advertising, Larry grew up in this business. His knowledge and experience of it are unmatched in Southwest Missouri.

Stuart Lipscomb


With a love for business and helping clients achieve their goals, Stuart joined his father in 2011 to help start Pioneer Outdoor.

Jeff LaRocca

Vice President, Sales

With extensive experience in the Southwest Missouri media market, Jeff has assisted his clients in growing their businesses through increased market participation and the right strategic choice of advertising mediums.

Cathy Briggs

Office Manager

Cathy is the heart and soul of Pioneer, and the company simply wouldn’t be what it is today without her experience and hard work.

Our History

As our company name suggests, Pioneer Outdoor was an early providers of quality outdoor advertising products in Southwest Missouri. Lester E. Cox used the original Pioneer Advertising company to promote his interests in TV and Radio stations across the Ozarks. It was not until his son-in-law, Jack E. Lipscomb, bought into the company and eventually took it over, that Pioneer began to grow through the construction and acquisition of hundreds of new billboard faces, turning Pioneer Advertising into a regional leader in billboard advertising. Jack E. Lipscomb was also very instrumental in the Outdoor Association of America and was a key player in national regulations for the entire billboard industry.


As Jack’s son, Larry, worked his way up to president of Pioneer Advertising, ultimately running the company after his father. Larry built hundreds of new billboards as the industry grew and sought out growth through acquisitions of many other outdoor advertising companies, a major one being Buena Vista Sign Company bought from Jerry Jones after the passing of his father Pat Jones. This took Pioneer Advertising into another level as they were now the main billboard company in the Ozarks.


With changes to the industry coming, Larry and Jack saw an opportunity to sell Pioneer Advertising’s assets to Lamar Advertising in 1997. It was not until 2011 that Larry would start Pioneer Outdoor and take on his son, Stuart, to learn the business. With the introduction of digital billboards, Pioneer Outdoor has continued their growth by selecting high quality locations to build and buy as opportunities arise and continue to do so into the new age of outdoor advertising.