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Rachel Bailey began their work experience as a Counselor at Camp JCC in 2016. Rachel then worked as an Intern at DELAWARE PACEM IN TERRIS INC from May 2017 to August 2017. In 2017, they also worked as a Server/Hostess at Lucky's Coffee Shop from June 2017 to March 2018. Rachel then served as a Server at Catherine Rooney's Irish Pub from March 2018 to August 2018. Rachel then worked as a Banquet Server at Harry's Hospitality Group from September 2019 to October 2020. From May 2020 to September 2022, they worked as a Sales and Marketing Coordinator at Pride Garden Products. Currently, Rachel is working as an Operations Assistant at Oppy starting in October 2022.

Rachel Bailey attended Concord High School from 2011 to 2015. Rachel then went on to pursue a Bachelor of Arts degree in Political Science and Government at the University of Delaware, where they studied from 2015 to 2019.