He enrolled at the University of British Columbia. He was redshirted in 2013. He was a four-year starter, playing right tackle and right guard. As a sophomore, he contributed to the team winning the Vanier Cup championship. As a senior, he was named a Canada West All-star at right tackle.[1]
Shepley was signed as an undrafted free agent by the New York Jets after the 2018 NFL draft on May 4.[3] He attended training camp and played three preseason games with the Jets before being released on August 31, 2018.
Saskatchewan Roughriders
Despite being signed by the New York Jets a week earlier, the Saskatchewan Roughriders of the Canadian Football League (CFL) selected Shepley with the fifth overall pick in the 2018 CFL Draft. Shepley signed a two-year deal with the Roughriders in March 2019.[4] Shepley made his CFL debut on June 13, 2019, against the Hamilton Tiger-Cats and started 14 games as a rookie. He was the unanimous selection for Saskatchewan Roughriders Most Outstanding Rookie.[5]
After the CFL canceled the 2020 season due to the COVID-19 pandemic, Shepley chose to opt-out of his contract with the Roughriders on August 25, 2020.[6]
San Francisco 49ers
On August 29, 2020, Shepley signed with the San Francisco 49ers of the NFL.[7] He was waived on September 5, 2020, and signed to the practice squad the next day.[8][9] He was elevated to the active roster on December 12 and December 19, for the team's weeks 14 and 15 games against the Washington Football Team and Dallas Cowboys, and reverted to the practice squad after each game.[10][11] He signed a reserve/future contract on January 4, 2021.[12]
On September 1, 2021, the Seattle Seahawks claimed Shepley off waivers.[14] Shepley played in 8 games during the regular season, blocking on the extra point unit. On August 31, 2022, the Seahawks waived Shepley as part of final roster cut downs.[15]
Dallas Cowboys
On September 1, 2022, the Cowboys signed Shepley to their practice squad.[16] He was promoted to the active roster on January 7, 2023, then waived two days later.
Indianapolis Colts
On January 10, 2023, Shepley was claimed off waivers by the Indianapolis Colts.[17] He was waived on August 29, 2023, and re-signed to the practice squad on September 21.[18][19] He was released on October 17.[20]
Dallas Cowboys (second stint)
On October 31, 2023, Shepley was signed to the Cowboys practice squad.[21] He signed a reserve/future contract on January 16, 2024.
Shepley was released by the Cowboys on August 27, 2024, and re-signed to the practice squad.[22][23]