Cunningham rose through the ranks. As a Sergeant, she worked as an Internal Affairs Investigator, a district Narcotics Unit Supervisor, a Uniform Patrol Supervisor, and an Executive Officer to a Deputy Chief. As a Lieutenant she worked in the Homeland Security Division, Traffic Branch and Special Events Planning. Cunningham is one of only five women to serve as a motorcycle officer.
Cunningham attended Purdue University and holds a Bachelor of Arts degree in Exercise Physiology / Movement and Sports Science. She is a graduate of the 240th session of the FBI National Academy and the 48th session of the Senior Management Institute for Police. She is an active member of IACP and FBINAA.