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Jessy Maggard has a diverse work experience spanning over several years. From 2002 to 2006, they worked as a Graphic Designer at Southern Wine & Spirits of Kentucky. Jessy then moved on to BrandMuscle, where they held various roles. From 2006 to 2019, they served as the Lead On-Site Graphic Designer. In 2019, they were promoted to Regional Manager - Creative Services, and in May 2021, they assumed the position of Director - Creative Services.

Jessy Maggard attended Ivy Tech Community College-Southeast from 1999 to 2001, where they earned an Associate of Arts (A.A.) degree in Design and Visual Communications, General.