After retiring from playing, Berry joined Tom Landry's Dallas Cowboys coaching staff as receivers coach. In 1970, after two seasons, Berry took a job with Frank Broyles at the University of Arkansas as receivers coach. In 1973 Berry joined Don McCafferty with the Detroit Lions as his receivers coach. In 1976, Berry joined former SMU teammate Forrest Gregg as his receivers coach with the Cleveland Browns. Berry joined the New England Patriots as receivers coach under Chuck Fairbanks in 1978. He stayed on with new coach Ron Erhardt until Erhardt and his entire staff were fired following a 2–14 1981 season. Berry left football and worked in real estate in Medfield, Massachusetts, until the Patriots fired Ron Meyer in the middle of the 1984 season and hired Berry to replace him. Under his leadership, the Patriots won four of their last eight games and finished the season with a 9–7 record. Berry's importance to the team was reflected less in his initial win–loss record than in the respect he immediately earned in the locker room – according to running back Tony Collins, "Raymond Berry earned more respect in one day than Ron Meyer earned in three years".