Skillestad is the owner/operator of Skillestad Simmentals, a dry-land ranch that has been in his family since 1908, maintaining a set of 150 to 180 cows and replacement heifers. Bulls are marketed through a production sale held in conjunction with Lassle Simmentals, while females are sold through private treaty and various consignment sales. A nine-year member of the Montana Simmental Association, he served two terms as MSA President. Currently, he is a member of the Dawson County Board of County Commissioners and had been active previously on school, church and agricultural boards. He earned a commission through the Montana Military Academy and spent 13 years in the Army and National Guard. Jim and his wife, Pat, have two sons and five granddaughters. Elected to the ASA Board in 2004, he has served in leadership positions on several committees and as ASA Treasurer.