Dickert began his high school career at Oconto High School in Oconto, Wisconsin.[2] 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,[3] and Jake finished his high school career at Kohler High School.[2]
Dickert graduated from Stevens Point in 2007 and joined Miech's staff as a graduate assistant for a year. He then moved to North Dakota State for the 2008 season, also as a graduate assistant. Head coach Craig Bohl promoted him to safeties' coach in 2009.[7][8] He left in 2011 to become special teams coordinator at South Dakota under Ed Meierkort, in what turned out to be his last year as head coach. Dickert replaced Chuck Morrell, who had left to become the head coach at Montana Tech.[9]
Dickert coached the defense for the 2014 and 2015 seasons under head coach Todd Hoffner. Minnesota State compiled a 24–3 record over those two seasons, including losing the 2014 NCAA Division II Football Championship to CSU–Pueblo. After two successful seasons, Dickert departed to become safeties coach at South Dakota State under long-time head coach John Stiegelmeier and defensive coordinator Clint Brown.[7] Dickert departed after the 2016 season to become safeties coach at the University of Wyoming. The move reunited him with Craig Bohl, now Wyoming's head coach but previously the head coach at North Dakota State from 2003 to 2013.[13] In 2019, Wyoming promoted Dickert to defensive coordinator after Scottie Hazelton departed for the same job at Kansas State.[14]
In 2020, Dickert received his first Power Five coaching position when he was hired as defensive coordinator by new Washington State head coach Nick Rolovich. Wyoming assistants AJ Cooper and John Richardson accompanied Dickert in his move to Pullman.[15] In October 2021, Washington State fired Rolovich and four assistant coaches, including Richardson, for refusing to comply with the state's COVID-19 vaccination mandate. Dickert then took over as acting head coach.[16] On November 27, 2021, Washington State announced the naming of Dickert as their permanent head coach; the promotion came a day after the Cougars finished the regular season with a resounding 40–13 win over in-state rival Washington in the Apple Cup.
Wake Forest hired Dickert to be their head coach in December 2024, following the resignation of Dave Clawson.[17]