Head of School

American Montessori Society Inc; Timonium (MD); On-site; USD 180,000 - 210,000; Full time

Job summary

Greenspring Montessori School seeks a thoughtful, experienced Head of School to begin July 1, 2027. The leader will uphold authentic Montessori principles while guiding strategic growth, enrollment, and long‑term sustainability across the Toddler through Adolescent programs.

The ideal candidate collaborates with the Board, faculty, and families to foster belonging, equity, and a warm, visible presence within the school community.

Qualifications

• Deeply knowledgeable about and committed to Montessori education.
• Warm, humble, approachable, and highly visible.
• An exceptional listener and transparent communicator.
• Strategic, entrepreneurial, and forward-thinking.
• Experienced in enrollment, advancement, and institutional stewardship.
• Skilled at building strong teams and organizational systems.
• Committed to equity, inclusion, belonging, and community partnership.
• Able to balance continuity with thoughtful innovation.

Responsibilities

• Articulate a compelling vision for the Toddler‑through‑Adolescent experience.
• Strengthen enrollment and retention.
• Broaden the school’s visibility and community partnerships.
• Support faculty and staff.
• Advance long‑term financial and institutional sustainability.
• Balance continuity with thoughtful innovation.

Skills

Montessori leadership

Strategic leadership

Enrollment management

Community engagement

Communication

Team building

Job description

Greenspring Montessori School

Head of School

Start Date: July 1, 2027

Co‑ed, Independent, Montessori School

Ages 18mos – Grade 8

223 students

10807 Tony Drive, Lutherville‑Timonium, MD 21093

www.greenspringmontessori.org

Educators Collaborative is pleased to be assisting Greenspring Montessori School in their search for a Head of School to begin July 1, 2027.

About the School

Located just outside of Baltimore and founded in 1962, Greenspring Montessori School is a vibrant Montessori community serving children from 18 months through 8th grade in Lutherville-Timonium, Maryland. With approximately 223 students, a dedicated faculty and staff, and a beautiful seven‑acre campus, Greenspring offers an authentic Montessori education grounded in curiosity, independence, confidence, and a deep respect for each child.

Students learn through hands‑on, experiential work, mixed‑age classrooms, meaningful outdoor experiences, and opportunities to connect their learning to the wider world. Greenspring’s distinctive Spanish/English Dual Language program, robust learning opportunities, and Adolescent Community further enrich an educational experience designed to support the whole child.

Greenspring is known for its warmth, strong relationships, commitment to belonging, and deeply rooted Montessori identity. The school welcomes families from a wide range of backgrounds, with 32 languages spoken at home and 33% of students receiving tuition assistance.

Mission

Greenspring Montessori School is committed to authentic Montessori education that nurtures curiosity, independence, confidence, and a lifelong love of learning. Rooted in Montessori’s tradition of peace education, the school strives to foster equity, justice, and belonging while helping students develop empathy, respect, and a sense of responsibility to one another and the wider world.

About the Opportunity

Greenspring Montessori School seeks a thoughtful, experienced, and mission‑aligned educational leader to serve as its next Head of School beginning July 1, 2027.

The next Head will follow a respected leader who has served the community for 15 years. This is an opportunity to honor and build upon Greenspring’s many strengths while helping the school become more connected, sustainable, visible, and prepared for the future.

Working in partnership with the Board, faculty, staff, and families, the next Head will articulate a compelling vision for the full Toddler‑through‑Adolescent experience, strengthen enrollment and retention, broaden the school’s visibility, support faculty and staff, and advance long‑term financial and institutional sustainability.

This is an exceptional opportunity for a leader who combines a deep appreciation for Montessori philosophy with entrepreneurial energy, strategic thinking, and strong organizational leadership.

The ideal candidate will bring:

• Deeply knowledgeable about and committed to Montessori education
• Warm, humble, approachable, and highly visible
• An exceptional listener and transparent communicator
• Strategic, entrepreneurial, and forward‑thinking
• Experienced in enrollment, advancement, and institutional stewardship
• Skilled at building strong teams and organizational systems
• Committed to equity, inclusion, belonging, and community partnership
• Able to balance continuity with thoughtful innovation

Above all, the next Head of School will be a relational and strategic leader who can preserve the warmth, trust, and authentic Montessori culture that define Greenspring while helping the school realize its full potential.

Greenspring Montessori School is committed to offering a competitive executive compensation package that reflects the scope and importance of the Head of School role. The anticipated base salary range is $180,000–$210,000, commensurate with the candidate’s experience, qualifications, and leadership background.

Greenspring offers a comprehensive benefits package, and the overall compensation package will be thoughtfully structured to attract and retain an exceptional leader who is deeply aligned with the school’s mission and prepared to lead Greenspring into its next chapter.

Non‑Discrimination Statement: Greenspring Montessori School welcomes all students and families, and does not discriminate in its hiring, admissions practices, or any other form of access on the basis of race, religion, national origin, sexual orientation, gender identity/expression, sex or disability.