[2] Montgomery was a four-year starter for the Iowa Hawkeyes football team from 1998-2002 under head coaches Hayden Fry and Kirk Ferentz.
Montgomery later played in the Arena Football League with the Chicago Rush, Colorado Crush, and Las Vegas Gladiators from 2003-2005.
In 2009, Montgomery moved west to serve as defensive line coach at Wyoming on the first staff of Dave Christensen, staying through the 2010 season.
[6] On February 12, 2015, the Green Bay Packers of the NFL confirmed that they hired Montgomery, giving him the title of "defensive front assistant".
[7] Montgomery stated that the Packers "offered an unbelievable opportunity" to pursue his dream of coaching in the National Football League.