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Kaitlyn Deasy started their work experience in 2006 as a Textile Artist for Nordstrom, specializing in women's bridge fashion. Kaitlyn then became a Director of Paper Products at Enchanté Accessories in 2007, where they were responsible for marketing and art direction, as well as managing key accounts with major US retailers. Kaitlyn worked closely with merchants to develop product assortments and merchandise plans for seasonal and special event purchases. Additionally, they served as an Art Director for a home accessories company, focusing on paper and textile consumer goods.

Kaitlyn Deasy attended Aquinas from 1996 to 2000. Kaitlyn then pursued their higher education at Syracuse University from 2000 to 2004, where they obtained a Bachelor of Fine Arts (BFA) degree with a focus on Surface Design.