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Gary Fennessy began their work experience in 1982 at Northwestern Memorial Hospital, where they served as the Vice President of Operations for over 30 years until 2013. Following this, in 2013, they joined Northwestern Medicine as the VP & Chief Supply Chain Executive. Additionally, in 2015, Fennessy took on a role as an Adjunct Faculty member at Loyola University Chicago.

Gary Fennessy earned their Master of Business Administration (MBA) with a focus in Accounting and Business/Management from DePaul Driehaus College of Business from 1983 to 1985.