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 provider of quality outdoor advertising in Southwest Missouri. Lester E. Cox used the original Pioneer Advertising to promote his business 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, growing the company and turning it into a regional leader in billboard advertising. Jack E. Lipscomb was also extremely instrumental in the Outdoor Association of America and a key player in national regulations for the entire billboard industry.


Jack’s son, Larry, worked his way up, becoming president of Pioneer Advertising. As the industry grew, Larry sought out growth for the company through the construction of new locations and the acquisitions of other outdoor advertising companies, becoming the largest billboard company in the region.


In 1997, Jack and Larry saw an opportunity to divest Pioneer Advertising’s assets to Lamar Advertising. 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 continues to grow, still seeking to provide the Ozarks with unmatched quality and experience in outdoor advertising.