For the first seventeen years of his career, Jim held positions that included sales, underwiting (commercial and personal lines), and marketing. He worked for various companies including Grain Dealers Mutual, Commercial Union, Meridian Insurance, and Monroe Guaranty. In October of 2001, he founded Dale Insurance in Peru Indiana.
He attained a Certified Insurance Counselor (CIC) designation in 1988, an Associate in Underwriting (AU) designation in 1995, and a Chartered Property & Casualty Underwriter (CPCU) designation in 1998
Jim grew up in Indianapolis, Indiana graduating from Lawrence Central High School and received a Bachelors' Degree from Ball State University.