Head of Upper School; Grades 5-8

Academic Leadership Annapolis,MD Posted Feb 26, 2026

St. Anne's School of Annapolis is an independent, co-ed, Episcopal day school located in Annapolis, Maryland serving students from two years old through Grade 8. The school is located near Washington D.C. and Baltimore, and is recognized for its progressive, inquiry-based education that is deeply rooted in a robust social-emotional learning (SEL) framework. They invest in the intellectual and spiritual promise of each student in a community that celebrates diversity and upholds the dignity of every human being.

Students are challenged to think critically and creatively, to know themselves as learners, and to govern their lives with confidence, compassion, and integrity.

The ideal Head of Upper School candidate will possess a passion for middle years experiential education and independent school leadership, the ability to inspire extraordinary educators, and excellent organization and communication skills, in addition to the other qualities outlined in the Position Profile for this role.

Interested candidates should send a resume, a letter of interest, a statement of educational and leadership philosophy, and a list of three professional references to Highley Thompson, at  Please do not contact the school directly.