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Hilltop Montessori School
Search being conducted by Educators Collaborative
Head of School / President Brattleboro, VT Posted Feb 21, 2026
$140,000 - $150,000
Job Description
Educators Collaborative is delighted to be supporting Hilltop Montessori School in Brattleboro, VT, in their search for a Head of School to begin July 1, 2027. This is a wonderful opportunity for a school leader who believes in authentic Montessori education and is eager to guide a close-knit community into the future.
About The 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 Opportunity
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:
Learn more on the Information for Candidates, which includes the full Leadership Profile and more details about the school.
How To Apply
Carole Everett and Debbie Millon, of Educators Collaborative (EC), are assisting Hilltop with this search. Please reach out to either consultant below to receive the EC Candidate Summary Sheet and the EC Disclosure Form, both required components of a completed application. Interested candidates are asked to submit the following materials in a single merged pdf file to Carole Everett or Debbie Millon. Dossiers will be reviewed upon receipt.
ceverett@educatorscollaborative.com
917-494-2574
Debbie Millon, Educators Collaborative
dmillon@educatorscollaborative.com
Opportunity Statement
Introduction to the Job/School
Opportunity Statement and Application Instructions
Job Details
Region New England (CT, ME, MA, NH, RI, VT)
Location
Brattleboro , VT
Salary Range
$140,000 - $150,000
Category Head of School / President
Posted
Feb 21, 2026
About Hilltop Montessori School
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…
Visit Website
View Organization Profile
Back to All Jobs
Search being conducted by Educators Collaborative
Head of School / President Brattleboro, VT Posted Feb 21, 2026
$140,000 - $150,000
Job Description
Educators Collaborative is delighted to be supporting Hilltop Montessori School in Brattleboro, VT, in their search for a Head of School to begin July 1, 2027. This is a wonderful opportunity for a school leader who believes in authentic Montessori education and is eager to guide a close-knit community into the future.
About The 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 Opportunity
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
Learn more on the Information for Candidates, which includes the full Leadership Profile and more details about the school.
How To Apply
Carole Everett and Debbie Millon, of Educators Collaborative (EC), are assisting Hilltop with this search. Please reach out to either consultant below to receive the EC Candidate Summary Sheet and the EC Disclosure Form, both required components of a completed application. Interested candidates are asked to submit the following materials in a single merged pdf file to Carole Everett or Debbie Millon. Dossiers will be reviewed upon receipt.
- EC Summary Sheet (Contact consultant, Carole or Debbie, for this document)
- Letter of Interest addressed to the Search Committee
- Current resume
- Statement of Educational Leadership Philosophy
- A list of five or more professional references, with contact information (name, relationship to candidate, phone, and email)
- EC Disclosure Statement (Contact consultant, Carole or Debbie, for this document)
ceverett@educatorscollaborative.com
917-494-2574
Debbie Millon, Educators Collaborative
dmillon@educatorscollaborative.com
Opportunity Statement
Introduction to the Job/School
Opportunity Statement and Application Instructions
Job Details
Region New England (CT, ME, MA, NH, RI, VT)
Location
Brattleboro , VT
Salary Range
$140,000 - $150,000
Category Head of School / President
Posted
Feb 21, 2026
About Hilltop Montessori School
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…
Visit Website
View Organization Profile
Back to All Jobs
Salary : $140,000 - $150,000