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Lealon Winstead started their work experience in 1996 as a General Manager at Exhibitors Service Network, Inc. In 2001, they transitioned to Imagecraft Exhibits as a Project Manager, where they gained skills in custom exhibit fabrication and project facilitation. In 2002, they joined 2020 Exhibits as National Director and Rental Director, responsible for managing exhibits and environments. Currently, they hold the position of Vice President in charge of exhibits and environments. Throughout their career, Lealon has gained expertise in custom exhibits, rental inventories, estimating, sourcing, and procurement.

From 1993 to 1995, Lealon Winstead attended The Art Institutes, but no degree or field of study information was provided.