Head of School

Hilltop Montessori School is initiating a search for a Head of School for the 2027-28 school year and beyond. A full Position Statement will be available to candidates in March 2026. In the meantime, interested candidates should send a letter of interest and resume to the Board of Trustees and Head of School Search Committee Chair, Courtney Deal, at headsearch@hilltopmontessori.org. 

Hilltop Montessori School in Brattleboro, Vermont is a thriving, authentic Montessori school, whose core values of critical thinking, social justice, independence, and creativity have built a strong community of life-long learners over the past 54 years. As the school looks ahead, we are excited to welcome a new Head of School beginning in the 2027-28 school year.  

Particular areas of strength include: Re-acreditation with the American Montessori Society will be completed in 2027; fully paid-for facilities located on 43 acres; a sizable investment fund and an Indexed Tuition program supports economic diversity among the student families; tuition assistance is further supported by Vermont’s Child Care Financial Assistance Program; an authentic Montessori curriculum implemented with fidelity at all levels by a dedicated and passionate teaching staff Toddler through Middle School, that incorporates an anti-bias curriculum along with a focus on addressing community mindfulness, social justice, and climate change.  

Hilltop Montessori School was founded in 1972 and relocated in 2009 to a 43-acre hill overlooking the Connecticut River Valley. The campus includes: two Toddler classrooms (15-36 months); two Children’s House classrooms (3-6 years); one Lower Elementary classroom (6-9 years); one Upper Elementary classroom (9-12 years); one Middle School classroom (12-14 years) occupying its own house with comparable facilities; 133 students / 35 faculty-staff; learning Specialist Team and Social Emotional Learning Coordinator (who leads the schools Child Study Team) to support a diversity of learners; a fully equipped kitchen area and an Elementary art room in the main building; integrated computer use at the Upper Elementary and Middle School levels; woods and trails for hiking and cross country skiing, gardens, a greenhouse, and a pond; and an Arts Barn, built in 2013, that includes a staff/event kitchen, gymnasium, expanded music facilities, and a theater

https://www.hilltopmontessori.org