Head of Upper School (Grades 5-8)

Search being conducted by Educational Directions

Academic Leadership Annapolis, MD Posted Feb 26, 2026
St. Anne's School of Annapolis

Job Description

St. Anne's School of Annapolis has launched a search for its next Head of Upper School (Grades 5-8), whose term will start July 1, 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. 

Application Instructions

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 Highley.Thompson@edudx.com. Please do not contact the school directly.

Job Details

Region Mid-Atlantic (DC, DE, MD, VA, WV)
Location
Annapolis , MD
Category Academic Leadership
Posted
Feb 26, 2026

About St. Anne's School of Annapolis