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Jessy Hart has a diverse work experience in various industries. Currently, they are working as a Human Resources Coordinator at Winmark - the Resale Company since August 2022. Before this, they worked at MGM Wine & Spirits, where they held the positions of Store Manager from November 2021 to August 2022 and Assistant Manager from February 2021 to November 2021. Prior to that, they worked at Orange County Library System as a Circulation Clerk from August 2018 to November 2020 and as a Customer Service Tech from May 2017 to August 2018. They also worked as a Circulation Clerk at the same company from September 2015 to May 2017.

Before joining the library system, Jessy worked at Walt Disney World. They worked as a Merchentainer: Emporium from March 2016 to July 2016 and as an Attractions Hostess: Splash Mountain from April 2015 to March 2016. They also had a brief role as a Home Coordinator at Quality Care Services from January 2015 to April 2015.

In 2014, Jessy participated in the Disney College Program Internship at Walt Disney World, where they worked as an MK Parking Hostess & MK Autoplaza from June 2014 to January 2015. Prior to that, they worked as a Student Worker at Aramark from August 2011 to May 2014.

In addition, Jessy has experience in coordinating special programs as the Special Programs Coordinator at Loras College Activities Board from August 2013 to February 2014. They also worked as a Peer Assistantship at Loras College Psychology Department from August 2013 to December 2013. Before these roles, they worked as Kitchen Staff at Uncle Vito's Pizzeria and Briggs Lake Liquor Store from June 2013 to August 2013.

Jessy Hart attended Becker Senior High School from 2006 to 2010 and obtained a High School Diploma. From 2010 to 2014, Jessy studied at Loras College, earning a Bachelor of Science (B.S.) degree in Psychology with a minor in Biology. Later, from 2015 to 2019, Jessy attended Southern New Hampshire University and completed a Master of Science (M.S.) degree in Industrial and Organizational Psychology. In addition, in October 2010, Jessy obtained a certification called VIRTUS from VIRTUS institution.