After graduating from Dartmouth in 1911, Ryan began his coaching career at St. Thomas College in Saint Paul, Minnesota, where he was the school's first resident athletic coach. He moved to
Milwaukee, Wisconsin, in 1914, where he worked for a flour milling firm based in
Minneapolis, Minnesota. He joined the football team at Marquette University in 1916 as an advisory coach under fellow Dartmouth alumnus,
John B. McAuliffe. Ryan replaced McAuliffe as head coach the following year and held the post for five seasons, during which he compiled a record of 28–5–5. He returned to his alma mater in 1922 to serve as an assistant to
Jackson Cannell. In March 1923, Ryan was hired as the head football coach at the University of Wisconsin. He was also given the title of assistant professor and paid an annual salary of $6,000. Ryan helmed the
Badgers football team for two seasons, tallying a mark of 5–6–4. He moved to
Northwestern University in 1925, where he was the ends coach for five seasons under
Glenn Thistlethwaite and
Dick Hanley. Ryan returned to Hanley's staff as an assistant coach and scout in 1934, and continued on under
Pappy Waldorf until 1939. ==Later life and death==