As an assistant, Montgomery coached several NFL players including Ben Roethlisberger and Terrell Owens.
Montgomery was a 2003 finalist for the Broyles Award, given annually to the nation's top college football assistant coach.
[4] In 2023, Montgomery was hired as an offensive analyst for East Carolina University under head coach Mike Houston.
[6][7][8] Brown was fired on November 18, 2024 and Montgomery was named interim head coach for the final two games of the season.
[10] After one year with UMass, he was hired as the offensive coordinator for Dartmouth under heads coach Sammy McCorkle.