Hilltop Montessori School

Head of School

Start Date: July 2027

LOCATION

Brattleboro, VT

GRADES

15mos-8th grade

ENROLLMENT

135

TYPE

Co-ed, independent, day school

WEBSITE

hilltopmontessori.org

Partners

About Hilltop Montessori School

Founded in 1972, Hilltop Montessori School is a warm, inclusive, and deeply relational independent school serving students from 15 months through Grade 8. Located on a beautiful 43-acre campus in Brattleboro, Vermont, Hilltop is widely respected for its authentic Montessori practice, progressive values, strong academic program, and commitment to educating thoughtful, independent, and socially conscious children.

Hilltop’s mission is for students to practice responsible independence in a caring community of curious, critical learners, and thoughtful citizens. Montessori principles are deeply woven throughout the program, from carefully prepared environments and uninterrupted work cycles to experiential learning, environmental stewardship, and adolescent internships in the broader community.

With devoted faculty, engaged families, a distinctive Middle School program, and a strong commitment to equity, access, and belonging, Hilltop offers an exceptional educational experience rooted in joy, rigor, and community.

Why Brattleboro?

Nestled in southeastern Vermont, Brattleboro is a vibrant and creative New England town known for its arts community, environmental consciousness, civic engagement, and exceptional quality of life. Surrounded by natural beauty and rich in culture, Brattleboro offers an inspiring setting for educational leadership, with easy access to colleges, independent schools, and outdoor recreation year-round.

About the Position

Following 13 years of stable and respected leadership, Hilltop is entering an exciting new chapter. The next Head will inherit a school with a strong Montessori identity, dedicated faculty and staff, engaged families, and a healthy partnership with the Board of Trustees.

This is an exceptional opportunity for a collaborative leader who values authentic Montessori education, child-centered learning, and strong community relationships. The next Head will help guide Hilltop’s future by strengthening enrollment, ensuring long-term financial sustainability, supporting strategic planning, and stewarding campus and programmatic growth.

Desired Qualifications

The ideal candidate will bring:

A deep understanding of Montessori philosophy and child-centered education
Strong educational and organizational leadership experience
Financial and operational acumen
Advancement and enrollment management experience
A warm, relational, and community-centered leadership style
A commitment to diversity, equity, inclusion, and belonging
The ability to balance continuity with thoughtful innovation

Above all, Hilltop seeks a visible, compassionate, and mission-driven leader who values children, respects faculty expertise, and will steward the school’s distinctive culture into its next chapter.

Compensation

The annual salary for the Head of School position is $140,000-$150,000.

How to Apply

Listing date: July 17, 2026

Carole Everett

Debbie Millon

Hilltop Montessori School complies with all applicable state and federal nondiscrimination statutes, including the Vermont Public Accommodations Act (9 V.S.A. Chapter 139), the Vermont Fair Employment Practices Act (21 V.S.A. Chapter 5, Subchapter 6) and Vermont State Board of Education rules 2226.6 and 2229.1. Hilltop Montessori School does not discriminate on the basis of race, color, religion, national origin, marital status, sex, sexual orientation, gender identity or disability in the administration of its educational policies, admissions, scholarships and other school programs. The school affords each of its students its full range of social, academic, and athletic opportunities.

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