After his military discharge, he became a sales manager in a small business selling stereo equipment until deciding in 1976 that he wanted to become an American football coach.
Berry began his coaching career in 1976 at the University of New Hampshire, his alma mater, before working with Penn State's offensive line in 1978.
He then spent two years coaching Boston College's offensive line before moving on to his 17-year stay at the University of Massachusetts Amherst.
[2] He was an assistant with the UMass Minutemen football team from 1981 to 1997, coaching running backs, quarterbacks, and the offensive line over his tenure.
Berry spent only one year at Richmond before moving to Montreal, Quebec, Canada to join the Alouettes in the Canadian Football League (CFL).
[3] During this time Montreal had three players named as the CFL's Most Outstanding Lineman, Uzooma Okeke in 1999, Pierre Vercheval in 2000, and Bryan Chiu in 2002.
After guiding the team to a 9–9 record in the 2006 CFL season, he took the Bombers to their first playoff game since 2003, but ended up losing to the Toronto Argonauts in the East Division semi-final.