He played college football at Ohio State and was signed by the Tennessee Titans as an undrafted free agent in 2018.

In the 2017 Cotton Bowl, the final game of his college career, Webb returned an interception for a touchdown in a win over USC.

[3] After going unselected in the 2018 NFL draft, Webb was signed by the Tennessee Titans as an undrafted free agent.

[5] After going unsigned in 2019, Webb signed a contract with the Saskatchewan Roughriders of the Canadian Football League (CFL) in April 2020.

[7] After beginning the season on the practice roster, he was promoted to the active team prior to their week 6 matchup with the Winnipeg Blue Bombers.