Cregg began his coaching career at his alma mater, Colorado State University, where he was a graduate assistant from 1997 to 1999. He was the defensive line coach at Colgate University from 2000 to 2003 at the University of Idaho.
From 2014 to 2016, he was the assistant offensive line coach for the Denver Broncos. During the 2016 season, the Broncos won Super Bowl 50.[3]
LSU
In 2019, he coached for LSU as an offensive line coach and running game coordinator, as LSU won the 2020 College Football Playoff National Championship. Also in 2019, LSU's offensive line won the Joe Moore award for the Most Outstanding Offensive Line Unit in College Football.
San Francisco 49ers
On March 7, 2022, it was announced that Cregg was returning to the NFL to become an assistant offensive line coach for the San Francisco 49ers.[4]