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Caroline Gesell began their work experience in 2017 as a Community Assistant at Greystar's 400 Meeting Street Apartments. Caroline then worked as a Community Assistant at MY HOUSE on Meeting under Alpha Management Partners. In 2018, Caroline served as a Research Assistant at BVL Historic Preservation Research and later joined CycleBar as part of their Front Desk Staff. Caroline also held the role of Risk Management Chairman for the Alpha Nu Chapter of Tri Delta. Caroline then interned with the City of Charleston's Board of Architectural Review before becoming the Academic Chair for the Thomas Jefferson Chapter of the Society of Architectural Historians. In 2020, they interned with the Preservation Foundation of Palm Beach. Caroline's most recent roles include Customer Success Associate and Customer Account Analyst at PlanSource, starting in 2021 and 2022 respectively.

Caroline Gesell received their Bachelor of Arts degree in Historic Preservation and Community Planning from the College of Charleston in 2019. Following this, they pursued their Master of Architectural History from the University of Virginia, which they completed in 2021. In March 2018, Caroline obtained a certification in AutoCAD 2016 Essential Training from LinkedIn.