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Sean Callahan has a diverse work history that spans from 2004 to present. Sean started their career as a Golf Professional at Elite Golf Cruises and worked there from July 2004 to September 2008. Following that, they joined Westgate Resorts as a Guest Services Assistant Manager from September 2008 to April 2012. In 2012, they briefly worked as a Caddie at Pebble Beach Company from April to June. Later that year, they started their own business called Snow Country Limousine, where they currently serve as the Owner-Operator since July 2012. In September 2013, they joined Westgate Resorts again, this time as a Guest Services Supervisor and also served as a Department Trainer until December 2014.

Sean Callahan attended the Golf Academy of America from 2002 to 2003, where they earned an Associate of Arts degree in Applied Business.