A Newark, Ohio native, Montgomery attended Newark Catholic High School where he helped the Green Wave to two state championships.
Montgomery played quarterback at North Carolina State University in the late 1980s. He ended his career with 5,298 yards passing and 31 touchdowns. In 1989, he passed for 535 yards in a game against Duke, which still stands as NC State's single-game record. He was also named MVP of both the 1988 Peach Bowl and 1989 Copper Bowl.
After spending four years as an assistant at Miami University, Montgomery became the RedHawks' 32nd head coach succeeding Hoeppner, who became head coach at Indiana University. In his first year the RedHawks posted a 7–4 record including a tie for first place in the MAC East division. University of Akron won the tie breaker and represented the East in the MAC Championship Game. On November 29, 2008, Montgomery resigned as Head Coach of the RedHawks, after four seasons and a 17–31 record.
On December 26, 2017, Montgomery was named the new offensive coordinator at Charlotte after spending the previous 8 years as the offensive coordinator at Youngstown State University.
On May 12, 2021, Montgomery was named the new offensive coordinator for the Buffalo Bulls.[1] His first season saw the Bulls drop from the fifth-most points per game among 128 Football Bowl Subdivision (FBS) teams to 57th-most of 130 FBS teams.[2][3] After the 2022 season it was announced that he was no longer with the Bull's football program.[4]
On February 15, 2024, Montgomery was named the offensive coordinator and quarterbacks coach for the University of Massachusetts Amherst under head coach Don Brown.[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.[9] UMass hired Joe Harasymiak as its permanent head coach on December 4.[10]
