Undersheriff Bobby Richardson began his career in law enforcement in 2007 with the Kendall County Sheriff’s Office as a patrol deputy.  During his career, Undersheriff Richardson has spent several years working uniform patrol assignments, as well as plain clothes assignments/undercover operations with the Kendall County Cooperative Police Assistance Team (KCPAT).  Undersheriff Richardson was also a member of the Kendall County Sheriff's Office Community Policing Unit, during which time he was also a School Resource Officer.  In addition to his other job responsibilities, Undersheriff Richardson volunteered to be a member of the Kendall County Special Response Team (SRT) and to be an instructor in multiple areas of law enforcement to include defensive tactics, firearms, and active shooter training.  Undersheriff Richardson is actively involved with the Sheriff’s Office Auxiliary program, and has helped assist in many programs and events throughout the county.  He is a Sheriff’s Office liaison to many communities within the county, and has volunteered his time with the Special Olympics Polar Plunge and Law Enforcement Torch Run.

Undersheriff Richardson was promoted to the rank of Sergeant and then to the rank of Deputy Commander in the Operations Division.  He was then promoted to the rank of Commander of the Corrections Division.  In November of 2019, he was promoted by Sheriff Baird to the rank of Undersheriff where he currently oversees the Operations Division of the Sheriff’s Office.

Undersheriff Richardson is a veteran of the United States Marine Corps, where he served in Operation Enduring Freedom and Operation Iraqi Freedom.  He attended Aurora University where he graduated summa cum laude with a Bachelor’s Degree in Criminal Justice.  He is a graduate of the Suburban Law Enforcement Academy, and a Trilogy member of the FBI Law Enforcement Executive Development Association.  Undersheriff Richardson is a member of the Kendall County Association of Chiefs of Police, the Illinois Association of Chiefs of Police, the International Association of Chiefs of Police, the Illinois Sheriffs Association, and the National Sheriffs Association.