[1] Sherman began playing rugby at Piedmont High School (east SF Bay area).
During his time playing fly-half for California the Golden Bears won 4 consecutive National Championships.
After graduating from Cal, Sherman played in England for Oxford University while earning his master's degree.
[8] He led the Black Knights to an undefeated fall season and a Rugby East conference championship in 2018.
His ‘21/‘22 Army West Point squad finished the season with a 14–1 record, winning the Patriot League title and the D1A National Championship.