[7] Skipper was signed by the Pittsburgh Steelers as an undrafted free agent in 2019.

After making the Steelers initial 53-man roster, Skipper was waived prior to Week 1 on September 7, 2019.

[11] On November 19, 2019, Skipper was re-signed by the Steelers off the Giants practice squad.

[15] He was elevated to the active roster on November 21, November 28, December 5, and December 12 for the team's weeks 11, 12, 13, and 14 games against the Baltimore Ravens, Indianapolis Colts, Cleveland Browns, and Jacksonville Jaguars, and reverted to the practice squad after each game.

[26] After the Titans were eliminated in the Divisional Round of the 2021 playoffs, he signed a reserve/future contract on January 24, 2022.

On November 17, 2022, Skipper was drafted by the Seattle Sea Dragons of the XFL.