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Chelsea Bennett has over nine years of professional experience in the service industry. Chelsea began their career in 2012 as a Server at Figlio. In 2013, they took on a similar role at Edgewild Restaurant and Winery. In 2015, they worked as a Server at Ditka's Restaurant in Chicago, and as a Design Assistant at Lauren Ziol Design, Inc. Chelsea also worked as an Account Coordinator at ADROC Productions. In 2016, they worked as a Server at DMK - Ada St. In 2017, they worked as a Server at Coda Di Volpe. In 2018, they were a Manager/Baker at Voodoo Doughnut, LLC (Mile High Location). In 2020, they were an Associate Team Leader at Whole Foods Market. Currently, they are an Operations Communications Coordinator at Avatara.

Chelsea Bennett attended the University of Dayton from 2010 to 2014, graduating with a Bachelor of Arts (B.A.) in Engilsh and a Bachelor of Arts (BA) in English Language and Literature, General.