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Oliver Stephenson has worked in a variety of roles since 2005. In 2005, they were a Sales Representative for Unicel. From 2006 to 2019, they worked in various roles for JorgeCruise.com Inc., including Managing Director, Coordinator of all projects for New York Times Bestselling Author, Multi-Million Dollar Launch Artist, Online Subscription Service Coordinator, Director of Photography, Videographer, Video Editor, Marketing Editorial overseer, Facebook Advertiser, Director of Exercise Creation, Celebrity Executive Chef, Food Stylist, In-House PR Consultant and National TV Segment Collaborator. From 2016 to 2018, they were the Owner of Stoking Fire Productions, shooting content and taking original footage and making it impactful. From 2016 to 2019, they were the Sales Manager for Techleus Web Design. Finally, from 2018 to 2019, they were the Videographer/Editor for Speed Society. In 2019, they were also the Marketing Director for Payment Logistics.

Oliver Stephenson attended UC San Diego from 2006 to 2007, studying Internet Marketing.