In 1999, Berry began with the Montreal Alouettes as their offensive line coach. 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. His O-line helped star running backMike Pringle win the CFL's rushing title in 1999 and 2000. The Alouettes won the Grey Cup in 2002. Berry was promoted to co-offensive co-ordinator and quarterbacks coach in 2003. In 2003, quarterbackAnthony Calvillo posted a career-high 5,891 passing yards and 37 touchdowns. Calvillo set more personal bests the following year with 6,041 passing yards and added 5,556 yards to his career total. Calvillo led the league in passing yards for both the 2003 and 2004 seasons. On December 15, 2005, Berry signed a multi-year contract to become the 26th head coach in Winnipeg Blue Bombers history. 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. After the 2006 season he was nominated for Coach of the Year, but lost to Wally Buono of the BC Lions. During the 2007 campaign, Berry's Bombers got off to a hot start, but struggled against division opponents in the closing weeks. As a result, the team finished one point behind the Toronto Argonauts in the East Division, despite leading in the division for much of the year, and did not earn a first round bye. However, the Blue Bombers won each of their first two playoff matchups, and earned a spot in the 95th Grey Cup. The team failed to capture the 2007 title, losing to the Saskatchewan Roughriders. The 2008 CFL season saw the Blue Bombers finish with an 8 wins, 10 losses season and a loss to the Edmonton Eskimos in the East semi-final playoff game. Berry was fired shortly after, on November 12, 2008. Berry spent the 2010 season as the offensive coordinator for the Saskatchewan Roughriders, but was fired after the eighth game of the 2011 season on August 19, 2011. On February 19, 2013, Berry was introduced as the senior advisor to the head coach of the Montreal Alouettes at a news conference in Montreal. Following the firing of Dan Hawkins after a 2-3 start to the season, Berry was promoted to run the offense in July 2013. Berry was dismissed by Jim Popp in November 2013 after Popp became the general manager and interim head coach of the Montreal Alouettes.
Personal life
Berry and his wife live in Florida. They have two daughters, Jessica and Kasey.