The Mountain School at Winhall
Head of School

Search led by IndySchool Consultancy (ISC)

About The Mountain School at Winhall

The Mountain School at Winhall (MSW) is an independent, nonsectarian Kindergarten through Grade 6 school located in Bondville, Vermont. Founded in 1998, MSW is intentionally small, relationship-centered, and deeply rooted in place-based, experiential learning. Vermont’s landscape serves as a living classroom, with outdoor learning integrated across seasons and disciplines.

Guided by its mission, MSW seeks to establish an educational foundation of curiosity, confidence, and competence, while practicing kindness to oneself, the community, and nature. The school is known for its inquiry-driven academics, multi-age learning, strong faculty-student relationships, and commitment to whole-child development.

Position Overview

The Mountain School at Winhall seeks a collaborative, mission-aligned Head of School to serve as the school’s chief executive and educational leader. Reporting to the Board of Trustees, the Head of School is responsible for advancing the mission, stewarding the school’s distinctive culture, and ensuring the long-term vitality and sustainability of the institution.

This is a highly engaged, hands-on leadership role in a small-school environment, requiring both strategic vision and daily presence with students, faculty, and families. The Head of School will partner closely with the Board, faculty, and community to strengthen academic excellence, support faculty growth, and guide MSW into its next chapter.

Key Responsibilities

• Provide vision and leadership aligned with MSW’s mission, values, and strategic priorities
• Advance academic excellence through inquiry-driven, experiential, and place-based learning
• Recruit, support, evaluate, and retain outstanding faculty and staff
• Foster a positive, inclusive, and mission-aligned school culture
• Oversee school operations, including budgeting, facilities, safety, and compliance
• Lead enrollment, admissions, and marketing efforts to support long-term sustainability
• Partner closely with the Board of Trustees on governance, strategy, and Head evaluation
• Serve as a visible ambassador for MSW with families, community partners, and external stakeholders

Ideal Candidate Profile

The ideal candidate will:

• Bring leadership experience in an independent school or comparable educational setting
• Demonstrate a deep appreciation for place-based, outdoor, and experiential education
• Balance strategic thinking with hands-on leadership in a small-school context
• Communicate clearly and build trust across a close-knit community
• Show strong emotional intelligence, integrity, and sound judgment
• Align educational leadership with institutional sustainability and governance best practices
• Demonstrate a commitment to equity, inclusion, and belonging
• Hold a master’s degree in education, leadership, or a related field

Application Process & Timeline

• Application Timeline: Review begins early 2026 and continues until the position is filled
• Start Date: July 1, 2026
• Opportunity Statement: https://doc.storydoc.com/EPbxkx
• Apply Now: https://tinyurl.com/4cxzp9u7

ISC Consultant:
Chris Brueningsen
chris@indyschoolconsultancy.com

Candidates are asked not to contact the school directly.

About The Mountain School at Winhall

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