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Jessica Dempsey has a wealth of work experience, beginning with their role as an Event Day Staff at the Consol Energy Center in 2011. Jessica then worked as an Account Executive for PLS Logistics Services in the same year. In 2013, they became an Assistant Manager at Enterprise Rent-A-Car. In 2014, they began their role as a Leasing Consultant for Cortland Partners. In 2016, they became a Human Resources Generalist for Nead Werx, Inc. and also worked as a Business Consultant for Momcierge in 2017. In 2018, they took on the role of Inventory Planning Analyst at Home Depot and, in 2023, they became Office Manager at Neuravest Research, Inc. and an Operations Consultant at Momcierge.

Jessica Dempsey completed their Bachelor of Science in Sports Studies at The University of Georgia in 2010. Jessica then went on to receive their Master of Business Administration from the University of Georgia - Terry College of Business in 2017. In addition, they obtained two certifications from Duolingo in 2016 - one in French Fluency: Elementary (Estimated).