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Jamie Sharpless has extensive work experience in various roles and industries. They began their career as a Post Production Intern at Engine Room in 2009 and later worked as a Broadcast production intern at Hill Holliday in 2010. Jamie then served as a Portrait Photographer on a contract basis at Image 1 Studios in 2011 and as a Senior Photographer at Vail Resorts. In 2012, they worked as a Production Coordinator at BrickyardVFX and as a Freelance Photographer, Video Editor, and Post-Producer at Jamie Sharpless Film and Photography. Jamie also worked as a Production Manager on a contract basis at ANGL Technologies Inc. in 2015 and held roles such as Email Marketing Manager and "Navigator" in Customer Operations at Hipmunk in 2016. They joined HOVER Inc. in 2017 and have held positions including Growth Manager, Strategy Lead in Business Operations, Senior Manager in Revenue Enablement, and currently serve as the Director of Product Operations.

Jamie Sharpless attended Connecticut College from 2007 to 2011, where they earned a Bachelor's degree in Film/Cinema/Video Studies.