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.