Jerry graduated from Goodrich High School in Fond du Lac in 1965, before attending the University of Wisconsin-Madison. He left school after about two years to enter the workforce; however, returned to UW at age 43 when he completed his B.A. in 1994. He went on to earn his M.S. in Social Work at the Madison campus.
Beginning in 1979, Jerry began a concurrent career in law enforcement as a part-time police officer for the Village of Shorewood Hills. He rose to Lieutenant in 1981 and was appointed Chief of Police in 1996 where he remained until he retired in 2004. Jerry then moved to the UW-Madison Police Department, where he served for three more years, retiring again, as Assistant Chief in 2007.