Cowden attended Lebanon High School in Virginia where he was one of the state's top multi-sport athletes,[1] playing football as a quarterback, baseball as an outfielder, basketball as a point guard and track and field.[2] He was a three-year starter in football and compiled an overall record of 30–6, leading them to the Region C, Division 2 championship in 1994 where they lost 34–33, in what was considered one of the greatest games in Southwest Virginia history.[2]
In 2000, after graduating from Wofford, Cowden was hired by the Carolina Panthers as a scouting assistant.[5] He had worked at a fireworks store on Asheville Highway before receiving the job with Carolina.[5] He became a scout for the southeast area in 2001, and served in the position through 2007.[6] Cowden served as a national scout from 2008 to 2012 and also added the position of senior college scout in 2012, which he served as until being promoted to assistant director of college scouting in 2014.[7]
Cowden was hired by the Tennessee Titans as director of player personnel in 2016.[8] He received a promotion in 2018 to vice president of player personnel.[9] In that position, he oversees the entire scouting department and assists with collegiate scouting, as well as helping prepare the team for the NFL Draft.[10] After Jon Robinson was fired as general manager of the Titans in December 2022, Cowden was named interim replacement.[11]
On May 22, 2023, Cowden was hired by the New York Giants as executive advisor to the general manager.[12] On January 13, 2025, the Giants let Cowden out of his contract to join the New England Patriots as a front office advisor.[13]