Penn attended Martinsville High School, where he practiced football and track.
* Second-team All-South Independent (1984) Penn was selected by the Dallas Cowboys in the second round (44th overall) of the 1985 NFL draft, to play as an outside linebacker.
[3] In the preseason against the Green Bay Packers, he returned an interception for a 77-yard touchdown.
[4] He started against the Cincinnati Bengals in place of an injured Rohrer, making 5 tackles and returned a blocked punt 49 yards for a touchdown.
In the 1988 offseason he was diagnosed with a degenerative spinal condition, that forced him to retire.