Cregg began his coaching career at his alma mater, Colorado State University, where he was a graduate assistant from 1997 to 1999.
[1] Prior to that, Cregg was an assistant offensive line coach with the NFL Oakland Raiders from 2007 to 2008.
In 2017, Cregg was the assistant offensive line coach for the Los Angeles Chargers.
[4] 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.
[6] On November 3, Cregg was fired alongside Luke Getsy and Rich Scangarello.