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Judy Jankowski has a strong background in educational leadership, with significant experience in admissions and school administration. Judy began their career as the Director of Admission at Quest Academy in 1999, where they worked until 2006. From 2006 to 2013, Judy served as the Director of Admission at McLean School of Maryland. In 2013, they transitioned to the position of Head of School at Chesapeake Bay Academy, where they oversee the day-to-day operations and collaborates with the board of trustees on strategic planning.

Judy Jankowski began their education in 2004 at National Louis University, where they pursued a degree in Educational Leadership. Judy completed their Doctorate in Education in 2007. Later, in 2009, Judy enrolled at The Johns Hopkins University to further their studies and obtained a Certificate of Advanced Graduate Study in Leadership in Independent Schools in 2011.