[1][2] Stephens refers to itself as "A portfolio of People", referencing the team members who work for the company.

Stephens Media started with stations around Tulsa, Oklahoma, before expanding to other markets.

On May 1, 2008, Stephens Media announced that it would acquire WFKL, WRMM-FM, and WZNE in Rochester, New York, as a part of Entercom's purchase of stations from CBS Radio in the market.

[3] In April 2018, Ingstad Radio sold 14 of its stations in Washington to Stephens Media Group.

[4] In July 2019, it was announced that the company would acquire 37 stations from Mapleton Communications.