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Courtney McChesney has a long and varied work experience. Courtney began their career in 2005 as a Customer Service Representative for The Student Book Store. In 2011, they moved to Atherton Hotel as a Banquet Captain. In 2015, McChesney took a role as Assistant Director and Family Involvement Coordinator at St. Pau's Christian Preschool. In 2017, they began working as a Bookkeeper for Duclos Consulting and Managment, LLC. Courtney also held a role as Property Accountant for Graduate Hotels in 2018. During the same year, they were also employed as Center Director for SUMMIT Early Learning. In 2020, McChesney began working as an Administrative Assistant for the Pennsylvania Association of Student Assistance Professionals (PASAP). Most recently, in 2021, they assumed the role of Staff Accountant for Territory Foods.

Courtney McChesney graduated from Pennsylvania College of Technology in 2011 with an Associate of Arts and Sciences (A.A.S.) in Early Childhood Education. Courtney then went on to attend Penn State University, graduating in 2017 with a Bachelor of Science (B.S.) in Human Development and Family Studies.