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Oshaira Mendez has worked in a variety of roles since 2007. Oshaira began their career as a Customer Care Center Intern at W Hotels before moving to the role of Executive Meeting Specialist at Westin Hotels & Resorts. Oshaira then served as a Sales Assistant at Sheraton before becoming a Sales Coordinator at Millennium & Copthorne Hotels. After that, they were a Sales Event Lead at TKP New York, Inc. followed by a Corporate Sales Manager at Earl Enterprises. Oshaira then moved to Kallman Worldwide Inc. where they held the role of Exhibitor Services Specialist for five years, before becoming a Project Manager at Metro Exhibits.

Oshaira Mendez obtained a Bachelor of Science in International Hotel & Tourism Management from Johnson & Wales University between 2004 and 2007.