Kaleb VanderMaiden joined Arlington/Roe in 2024 as a Transportation Underwriter. He has prior experience at J.M. Wilson, where he served as an assistant underwriter and renewal transportation underwriter for three years. His educational journey led him from Mendon, Illinois, to Illinois State University, where he graduated in 2021 with a degree in finance.

One of Kaleb’s favorite aspects of his career is the opportunity to meet people from across the industry and hear their unique stories. He finds fulfillment in providing agent partners and their insureds peace of mind by helping them find the right solution.

Outside of work, Kaleb is an active member of his community, helping to raise funds for leiomyosarcoma awareness and organizing fundraisers for the Fishing for Freedom organization alongside his mother. As an alum of the Pi Kappa Phi fraternity, Kaleb values the importance of giving back and supporting causes that are meaningful to him.

In his spare time, Kaleb enjoys watching basketball and football, especially as a dedicated Seattle Seahawks fan. He also prioritizes staying active, whether it’s through working out or hiking when traveling outside of the Midwest. Living in Chicago provides Kaleb with endless opportunities to explore the city with friends, try new activities, and attend concerts, as he’s a huge music fan across all genres.