Dickert began his high school career at
Oconto High School in
Oconto, Wisconsin. His father, Jeffrey Dickert, was the superintendent of the Oconto School District. The family moved to
Kohler, Wisconsin, for Jake's senior year after Jeffrey took the job of superintendent there, and Jake finished his high school career at
Kohler High School. The
University of Wisconsin–Stevens Point, then coached by
John Miech, recruited Dickert to play
quarterback, where he backed up future
Canadian Football League player
Scott Krause. He converted to
wide receiver for the 2005 season. His senior year in 2006 was interrupted by a case of
appendicitis, but he returned to the playing field two weeks after surgery. Dickert's seven receptions per game that year led the
Wisconsin Intercollegiate Athletic Conference (WIAC) and he was named to the second team all-conference. ==Coaching career==