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Jessica Gaskins has a diverse work experience in various roles and companies. Jessica is currently working as a Manager Strategic Communications at The Port of Virginia since October 2022. Prior to that, they worked at Capes Shipping Agencies as a Marketing Manager from July 2020 to October 2022. Jessica also worked at CV International, where they held two positions: Marketing Manager from July 2019 to October 2022 and Marketing & Administrative Coordinator from October 2017 to July 2019. Jessica's career began at Sentara Healthcare, where they worked as an Exercise Specialist from May 2014 to October 2017.

Jessica Gaskins' education history begins in 2009 when they attended Tidewater Community College, where they pursued an Associate of Science degree in Science. Jessica completed their studies there in 2012. Following that, they enrolled at Old Dominion University from 2012 to 2014 and obtained a Bachelor of Science degree. In 2017, Jessica pursued higher education at Regent University and completed a Master of Business Administration (MBA) program in 2019. Lastly, in 2023, they attended Virginia Wesleyan University for a certificate program in Environmental Sustainability.