College: Stephenson split his college career between the West Virginia University and Loyola University Chicago. In his first two years at West Virginia, Stephenson tallied four goals and three assists across 31 appearances, before transferring to Loyola. At Loyola, Stephenson recorded two assists in 24 games. Stephenson suffered a season-ending collarbone injury in his junior season before returning as a senior and earning a spot on the All-Missouri Valley Conference Second Team.
Before USL Championship: Stephenson was an integral part of the inaugural Kaw Valley FC team in USL League Two in 2018. Stephenson tallied nine goals in 11 appearances and earned Kaw Valley FC MVP honors, as well as being named to the USL League Two All-League team, All-Central Conference First Team, while he was also a two-time Central Conference Team of the Week honoree. Stephenson spent the previous summer in 2017 playing for fellow USL League Two side the Des Moines Menace.
Sporting KC Academy: During his time with the Sporting KC Academy, Stephenson scored nine goals across his final two U.S. Soccer Development Academy campaigns in 2013-14 and 2014-15.