Ryan joined his father in 2007 after seeing how much his Dad enjoyed his work. In 2015 he established Hillenbrand & Company as an independent insurance brokerage firm. Ryan focuses primarily on employee benefits for locally owned businesses and working with financial advisors assisting their clients on life, Medicare, long term care and disability insurance needs. Ryan and his wife Christine have 5 children and reside in Chesterfield. He is past President of the Missouri Association of Health Underwriters.

Jack started in the life insurance business in 1967 with Penn Mutual in downtown St. Louis, and eventually expanded into full service insurance and investment work at Moneta Group and later The Capital Group. Jack retired from the investment business in 2017 and still works with lifelong clients on their insurance and estate planning needs. Jack and his wife of 48 years, Lisa, reside in Creve Coeur.