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Jill Chiddy has a diverse work experience that spans over several years. Jill began their career as a Community Engagement Specialist at the Arthritis Foundation in 2006. Jill then worked as a Staffing Agent at Randstad in 2007. Jill then joined Globe Education Network, Corporate Offices in 2009, where they held various roles including Admissions Representative, Director of Admissions, Campus Director, and Director of Enrollment Services. In 2017, Jill became a Regional Manager at Children's Learning Adventure, where they oversaw the implementation of a STEAM-based curriculum. Most recently, they served as the Human Resources Director at Lupient Automotive Group, managing multiple franchise stores and service centers.

Jill Chiddy holds a Bachelor's degree in Economics from the University at Albany, SUNY. Jill pursued their higher education at Broadview College, where they obtained a Master of Business Administration (M.B.A.) with a specialization in Human Resource Management.