Leonard is a 1992 graduate of Central Washington University and began his insurance career in 1998. After spending nine years as a captive agent, Leonard opened his own independent agency in 2008. The agency merged with Oltman Insurance in July, 2014 and Leonard is now one of the managing partners of Oltman Insurance Agency.
Leonard grew up on a dairy farm near Ferndale in Whatcom County. He is licensed in all lines of insurance with specialization in Farm and Crop Insurance and is the only licensed Crop Insurance agent residing in Whatcom County. Leonard also manages the Life and Health division of Oltman Insurance.

Leonard enjoys spending time with his family, as well as coaching fastpitch softball and baseball and currently serves on a local school board. He and his wife Kim and their three children reside near Sumas.