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Keicy Tolbert has a diverse work experience in various administrative and educational roles. From 2016 onwards, they worked as the Chief of Staff at the Carnegie Foundation for the Advancement of Teaching. Prior to that, they served as the Executive Assistant to the President of the same organization from 2015 to 2016. In 2013 to 2015, they worked at Stanford University GSB as the Assistant Director for Evaluation, MBA Admissions. Before that, they were the Program Administrator for the University of Virginia Institute of the Humanities and Global Cultures from 2012 to 2013. Keicy Tolbert also worked at the University of Virginia Darden School of Business from 2009 to 2012 as the Executive Assistant to the Senior Associate Dean for Finance and Administration. Keicy'searliest work experience was as a Graduate Instructor of English at the University of Virginia from 2003 to 2009.

Keicy Tolbert holds a Ph.D. in English, which was obtained from the University of Virginia. Keicy pursued this degree from 2004 to 2011. Prior to their doctoral studies, they completed their Master of Arts in English at the same university from 2001 to 2004.