The current business climate has seen an unprecedented number of cybersecurity related headlines. Hackers to Nation State actors have been shown to be constantly probing Organizations defenses with the intent to break in, disrupt operations, monetize information, and steal intellectual property. Between these threats and the increasing regulatory climate, never has the Chief Information Security Officer (CISO) been asked to navigate more difficult terrain. Originally patterned after the Chief Information Officer (CIO) of the Year Award sponsored by the Association of Information Technology Professionals (AITP Chicago), SIM-Chicago and the Executive Club of Chicago, this program seeks to recognize outstanding CISOs for the contributions they make to their organizations, the Information Security profession and the local community. The award process is overseen by the Chicago CISO of the Year Program, which is a not-for-profit affiliated with AITP Chicago and managed by local area security leader volunteers.