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Jessica Grasmann has over 10 years of work experience. Jessica began their career in 2011 as a Lead Assistant Event Planner at Creations by Christine Events. In 2012, they worked as a Guest Service Associate at European Wax Center. The same year, they took on a role as a Cast Member at The Disney Store. In 2011, they were an Intern at OTR Global, where they assisted with organizing employee and client events. In 2014, they became an Assistant to the Media Team at David Tutera. In 2015, they worked as a Service Coordinator at Curtain Care Plus and as a Character Attendant at The Walt Disney Company. In 2017, they became an Office Manager at George the Chimney Guy. In 2018, they began working at Clarion Events - North America as an Exhibitor Services Manager and Office Manager and Assistant to Senior Vice President. Most recently, in 2021, Jessica became an Experience Operations Lead at Part and Sum.

Jessica Grasmann's education history includes a Bachelor of Science (B.S.) in Organizational Leadership from Penn State University from 2014 to 2017, an Associate of Arts (A.A.) in Humanities and Social Sciences from Rockland Community College from 2011 to 2013, and a high school diploma from Academy of the Holy Angels from 2006 to 2010.