Stewart has worked at Federated Insurance since 1983. He is currently a 1st Vice President and Director of Special Account Marketing at Federated Insurance. Federated is a national insurance company that specializes in business insurance programs and is headquartered in Owatonna, Minnesota. Born and raised in Florida, Stewart attended Maryville College in Maryville, Tennessee, where he played football and baseball. He graduated with a Business Administration degree and immediately went to work with Federated in a sales position back in Florida. He moved into sales management and eventually ended up in Atlanta, Georgia, where he and his family lived for 10 years before moving to in Owatonna, Minnesota in 2007. After eight years in Minnesota, he and his wife recently relocated to Woodstock, Georgia. Stewart married his wife Gloria in 1985. They have two children. Their daughter, Carlee, graduated Magna Cum Laude from University of Northwestern with a Music Education degree in 2011 and is teaching at Westminster Schools of Augusta in Augusta, Georgia. Their son, Will, graduated from Bethel University with a Physical Education degree in May of 2015 and got married in July 2015. Currently he is teaching and coaching in Hastings, Minnesota. Stewart has had numerous leadership roles in several of the churches he and his family have attended. He also helped establish an FCA huddle in Owatonna at the high school his son attended.