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Stefan Cassara has a diverse and extensive work experience. Stefan started their career in 2005 as an Operations Assistant at Shout! Factory and later worked as a Graphic Artist at Tyrant Snowboards from 2007 to 2011. Stefan then joined UBC International/MGM Grand Hotel & Casino as a Graphic/UI Design/Front End Development/Photographer, where they were responsible for event photography, front-end website development, and creation of social media marketing collateral. In 2014, they became the Visual Media Manager at JS Products, Inc. and was in charge of product and lifestyle photoshoots, video content production and editing, and design of marketing collateral. Additionally, they worked at LAMEHORSE MEDIA as a Creative Director, where they created brand identities, executed various design jobs, and cultivated client relationships. In 2020, they held multiple roles as a Senior Director - Creative and Creative Director at Troll Co. Clothing, Senior Creative Director at Welder Nation, and Senior Creative Director at Five Nine Whiskey.

Stefan Cassara attended the Academy of Art University from 2009 to 2011, where they studied Web & New Media. Stefan also obtained a certification in the Master Recording Program II, although details about the institution and date of completion are not provided.