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Jenna Spain has a diverse work experience spanning multiple industries. Jenna started their career in 2002 as a Shift Manager at Jamba Juice, where they managed employees and served customers. Jenna later worked as a Server at Point Break Surfin' Tiki Club, where they also handled advertising and promotions. In 2007, they joined Enterprise Rent-A-Car as a Management Trainee. In 2008, they became a Recruitment Specialist at Maxim Healthcare Services, recruiting medical coders and technicians and managing employees. Jenna then transitioned to a role at AmericanTours International, LLC, starting as a Travel Operations Coordinator and later becoming an Account Manager, Senior Operations Manager, and eventually the Director of Operations and Customer Relations.

Jenna Spain earned a Bachelor of Arts degree in Psychology from California State University, Long Beach. Jenna attended the university from 2001 to 2006.