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Jenna Stewart's work experience begins in 2002 as the Executive Director at Charlotte Jewish Preschool, a role they held for one year. From 2003 to 2010, they worked as a Child Development Specialist at Child Care Resources Inc. In 2011, they joined WW (formerly Weight Watchers) as a Wellness Coach, a position they held for 10 years. In 2021, they became a Special Education Classroom Assistant at RIVER VALE PUBLC SCHOOLS for 10 months before transitioning to their current role as a Learning And Development Specialist at The Children's Village.

Jenna Stewart attended The George Washington University from 1981 to 1984, where they pursued a field of study in Theatre/Theater. Jenna did not obtain a degree during this time. Later on, from 1991 to 1997, Jenna enrolled at Thomas Edison State University and successfully completed a Bachelor of Arts (BA) degree in Theatre/Theater.