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Jessica Beckles has held a variety of positions since 2004. Jessica began their career as Event Staff for Westfield Group/Westfield Insurance, followed by a role as Front Desk Supervisor at Wingate by Wyndham in Lynchburg, Virginia. In 2008, they were promoted to General Manager at Super 8. Jessica then moved to Grand Lucayan Resort; Our Lucaya; Radisson Our Lucaya Beach & Golf Resort as Reservation Supervisor/ Revenue Manager in 2010. In 2012, they became Office Manager/Administrator at Gregg & Valby, LLP DBA Affinity Lending Solutions, followed by a role as Office Assistant at Northwestern Mutual in 2014. In 2015, they were hired as Front Office Assistant at Northeastern Endodontic Specialists, and most recently in 2017 they began working as Sales Administrator at GradeCam.

Jessica Beckles attended Northwestern High School from 1999 to 2003 and then Liberty University from 2003 to 2007, where they earned a Bachelor of Science in Business Administration and Management, General.