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Gretchen Connolly has a diverse work experience spanning several industries. Gretchen began their career in 2010 as an Operations & Programs employee at the McLean County Chamber of Commerce. In 2011, they worked for the Normal CornBelters as a Fan Experiences Representative and Ticket Sales employee. Gretchen then joined McDonough District Hospital in 2012 as a Publications Writer before moving to Marcus & Millichap, where they served as a Certified Agent Support Specialist and Marketing Coordinator from 2012 to 2017. Currently, Gretchen is employed at ampliFI Loyalty Solutions, where they have held various positions. Gretchen started as a Digital Marketing Coordinator in 2017 and was later promoted to Client Marketing Manager in 2020. As of March 2021, they hold the position of Director of Marketing at ampliFI Loyalty Solutions.

Gretchen Connolly attended Illinois State University from 2007 to 2011, where they obtained a Bachelor of Science degree in Public Relations.