Cherundolo was hired by the Steelers as an assistant coach upon the end of his playing career. He coached with the Steelers from 1949 through 1958, leaving football in 1959. Cherundolo returned to the Steelers in 1960 as a part-time scout and returned as a full-time assistant coach for the 1961 season. He went on to coach for the Philadelphia Eagles with head coach and friend Nick Skorich in 1962 and 1963, then went on to coach with the Washington Redskins until 1966, when he coached for the Chicago Bears for a total of eight years, interrupted by a one-year coaching job for the Tri-City Apollos of Midland, Michigan. He coached a total of 22 years in the NFL with four teams.
