In addition to being the company's namesake, Webb served as CEO of Varsity Brands, a major manufacturer and distributor of sportswear and accessories. Webb also played a crucial role in 2022 when Human Events acquired the Canadian online magazine The Post Millennial. He helps run The Post Millennial as a publisher in his current position.

Varsity Brands, one of the world's significant suppliers of cheerleading and dance products and services, was founded and is led by Webb, who has served as CEO. Jeff Webb Herff Jones has been with the company since its inception in 1974 when he also served as CEO before becoming chairman in 2018. He is still involved with the company, though now only in an advising capacity.

Varsity Spirit, headquartered in Memphis, Tennessee, serves over a million players every year across the globe. Webb stepped away from Varsity Brands to concentrate on the International Cheer Union and Human Events.