Montgomery began a career in coaching while he was playing in the Arena League, working as an assistant at
Iowa City West High School and
North Iowa Area Community College. He later served as a
graduate assistant at
Northern Iowa in 2006, before being promoted to full-time defensive line coach for the 2007 and 2008 seasons.
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.
In January 2011, Montgomery briefly served as defensive tackles coach at
Indiana under head coach
Kevin Wilson.
[5] However, he was soon hired away by
Michigan and new head coach
Brady Hoke in February 2011. Montgomery served as defensive line coach for the Wolverines for the 2011 and 2012 seasons. With the Wolverines, Montgomery served as the chief recruiter for 5-star commitments
Derrick Green and
Ondre Pipkins[6]
From 2013-2014, Montgomery served as the defensive line coach at
Oklahoma under head coach
Bob Stoops, earning a salary of $325,000 in 2013 and $380,000 in 2014. He was promoted after two seasons with Oklahoma to co-defensive coordinator on January 6, 2015, where he was expected to lead the defense alongside
Mike Stoops.
[7]
His tenure as co-defensive coordinator with the Sooners was brief.
[8] On February 12, 2015, the
Green Bay Packers of the
NFL confirmed that they hired Montgomery, giving him the title of "defensive front assistant".
[9]Montgomery stated that the Packers "offered an unbelievable opportunity" to pursue his dream of coaching in the National Football League.
[10]
In January 2018, Montgomery was hired as the assistant head coach and defensive line coach on
Jimbo Fisher's staff at
Texas A&M.
[11] Later in January 2018, Montgomery instead opted to remain with the Packers as the defensive line coach on the reorganized staff of head coach
Mike McCarthy. Montgomery had spent 2 weeks recruiting on behalf of Texas A&M
[12]
In February, 2019 Montgomery joined Scott Frost and the Nebraska Cornhuskers as defensive line coach