Jessop attended Broad Run High School in Ashburn, Virginia, and he led the Spartans to a state championship during his sophomore season.
[1] Jessop was offered a scholarship to play football at the University of Richmond; however, he declined the school's invitation and joined his favorite college team, the Virginia Tech Hokies, as a walk-on.
[3] Jessop's first start for the Rams came on October 15, 2016, when he accounted for seven touchdowns (five passing, two rushing) in a 70–24 win over West Virginia State.
[6] At season's end, he was named the MEC Offensive Player of the Year, and he finished fourth in voting for the Harlon Hill Trophy.
[9] Ahead of the 2018 NFL draft, Jessop participated in a Pro Day at West Virginia University, where he performed well in the broad jump and 40-yard dash.