Jake Boss played college baseball at Division III Alma College from 1990 to 1993. In the mid-1990s, he began his coaching career at the high school and community college levels before joining Eastern Michigan as an assistant coach in 1997. After seven seasons at Eastern Michigan, Boss moved to Michigan, where he served as an assistant coach from 2005 to 2007.
In 2008, Boss was named head baseball coach at Michigan State. He led the Spartans to their first NCAA Tournament appearance in 2012, marking a significant milestone in his tenure.
Boss also had a brief stint as head coach at Eastern Michigan in 2007. Despite a challenging start with a 0-17 record, he turned the program around, guiding the Eagles to a 25-17 finish. Under his leadership, Eastern Michigan won the Mid-American Conference (MAC) Western Division title and the MAC Tournament, earning a spot in the NCAA Tournament.