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Jess Heitland began their work experience in 2000 as a Freelance Web Designer, working on various projects and roles including Designer, Front-end Developer, and Consulting. In 2001, they joined The Speedboat Gallery as a Co-Conspirator, showcasing local artists and musicians. In 2005, Jess started working at The Lacek Group as a Senior Designer, responsible for communicating brand strategies through design. In 2016, they were promoted to Associate Creative Director at the same company.

From 2000 to 2003, Jess Heitland attended the College of Visual Arts, where they pursued a Bachelor in Fine Arts degree with a focus on General studies.