Head of School

Position Summary

Westshore Montessori is seeking a compassionate, collaborative, and mission-driven Head of School to lead our school community. We are looking for a leader who is deeply aligned with Montessori philosophy, committed to educational excellence, and able to build strong relationships with children, families, and staff.

The Head of School is responsible for the overall leadership and success of the school. This role ensures that the school remains authentically Montessori in philosophy and practice, supports a strong and positive school culture, and provides clear leadership across academics, staffing, compliance, and operations. The Head of School serves as the school’s lead educational and administrative leader and is accountable for all major school matters. This role works in close partnership with the Director of Operations to maintain strong alignment and seamless execution across school operations.

About Westshore Montessori

Westshore Montessori School has been serving families since 1966 as a 501(c)(3) nonprofit devoted to authentic Montessori education. Rooted in respect for each child’s independence and development, Westshore offers a warm, child-centered community where children build a lasting foundation for learning and life.

What You’ll Do

Lead Montessori Practice and School Vision

• Uphold authentic Montessori philosophy and practice across the school
• Support high-quality classroom environments, including multi-age learning, uninterrupted work cycles, and thoughtfully prepared spaces
• Conduct regular classroom observations and provide coaching, feedback, and professional support to staff
• Foster a culture grounded in grace, courtesy, peace education, respect, and child-centered learning
• Support consistency and continuity of program quality across age levels
• Collaborate closely with the Board of Directors on school strategy, fundraising, and long-term direction and regularly report on financials, compliance, enrollment, staffing, and other key school matters.

Lead and Support Staff

• Recruit, hire, supervise, mentor, and evaluate staff
• Build a strong, respectful, and accountable professional culture
• Support staff development through coaching, reflection, and clear expectations
• Partner with the Board HR Committee, as applicable, on staffing and leadership matters

Oversee School Operations

• Work closely with the Director of Operations to ensure smooth systems, strong communication, and effective execution, and effective day-to-day operation of the school
• Oversee admissions, enrollment, family onboarding, staffing plans, and schoolwide planning
• Coordinate budgets, resources, calendars, events, and schoolwide priorities
• Ensure facilities, systems, and operations support a safe, organized, and Montessori-aligned environment

Ensure Compliance and Accountability

• Hold final accountability for Ohio childcare licensing compliance and related operational standards
• Oversee health, safety, sanitation, emergency preparedness, and required documentation
• Ensure readiness for inspections, proper recordkeeping, and timely compliance follow-through
• Address serious incidents, major parent concerns, and other high-risk or sensitive matters with transparency and care

Build Family and Community Relationships

• Cultivate strong, trusting relationships with families through open and respectful communication
• Lead tours, open houses, and outreach efforts that reflect the mission and values of the school
• Support conflict resolution with empathy, professionalism, and a Montessori-aligned approach
• Serve as a visible, steady, and welcoming presence within the school community

Qualifications

• Montessori credential required
• Bachelor’s degree required; Master’s degree in Early Education, Leadership, or a related field preferred
• 5+ years of Montessori teaching and/or administrative leadership experience
• Knowledge of Ohio childcare licensing requirements and early childhood best practices
• Strong leadership, communication, organizational, and relationship-building skills
• Demonstrated commitment to authentic Montessori practice and a peaceful, inclusive school culture

Set Yourself Apart

We are seeking a leader who brings:

• A deep commitment to authentic Montessori education
• A servant leadership mindset and a collaborative approach
• Strong communication and relationship-building skills
• Clear systems thinking and operational judgment
• The ability to balance mission, people, program quality, and school sustainability

Compensation and Benefits

Westshore Montessori is committed to transparency in compensation. The salary range for this position is $95,000 – $105,000, commensurate with experience.

Benefits include:

• Paid time off
• Professional development support
• Tuition discounts
• 401(k) match

Interview Process

Westshore Montessori is also committed to transparency in the hiring process. Candidates selected to move forward can expect a series of three meetings:

• one with the Director of Operations
• one with members of the Board
• one with several teachers from the school to support broader 360-degree feedback

Pay: $95,000.00 - $105,000.00 per year

Benefits:

• 401(k) matching
• Paid time off

People with a criminal record are encouraged to apply

Work Location: In person