Head of School

Exciting Head of School Opportunity!

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-accreditation with the American Montessori Society will be completed in 2027.
• Two recent and ongoing renovations aimed at sustaining and expanding current and future community needs, including:
• A second toddler classroom in 2025.
• A new STEM space to support an expanding STEM curriculum in 2026.

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
• An Arts Barn, built in 2013, that includes a staff/event kitchen, gymnasium, expanded music facilities, and a theater

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Head of School Search

Hilltop Montessori School is initiating a search for a Head of School for the 2027-28 school year and beyond. Below is the current Head of School job description; a full Position Statement will be available to candidates in March. In the meantime, interested candidates should send a letter of interest and resume to Board of Trustees and Head of School Search Committee Chair, Courtney Deal, at (Use the "Apply for this Job" box below).

Title:

Head of School

Reports To:

Board of Trustees

Overview

Hilltop Montessori School faculty and staff members understand and promote the school’s mission, vision, objectives, and policies both within and outside the immediate school community. Faculty and staff are expected to attend to each child’s and adult’s individual needs with warmth, guidance, and humor, and to model with their team members the same attributes.

The Head of School is a collaborative member of the administrative team, and must embrace and be able to speak to Hilltop’s mission as a Montessori school.

RESPONSIBILITIES

The Head of School will be responsible for implementation of the following:

Education

• Review and approve the annual curriculum for each program.
• Monitor classroom activity to assess compliance with approved curricula, adherence to the Montessori philosophy, and ongoing results/performance.
• Ensure that the curricula and lessons have an eye to diversity, equity, justice, and inclusion.
• Conduct regular meetings with teachers.
• Hire and retain quality teachers.
• Conduct annual performance reviews of teachers. Provide staff development opportunities.

Management

• Establish operating policies.
• Ensure that school policies and practices consider the values of diversity, equity, justice, and inclusion.
• Establish job descriptions (who is responsible for which activities/results). Conduct regular meetings with administrative staff.
• Hire and retain quality staff.
• Conduct annual performance reviews of…