Head of School (Chief Executive Officer)

 Montessori School of Waukesha, Inc. — Waukesha, Wisconsin

 Start Date: June 1, 2026 (ideally sooner)

 Application Deadline: February 1, 2026

 Reports to: Board of Trustees

About Our School

Montessori School of Waukesha (MSOW) is a thriving, private, independent Montessori school located in Waukesha, Wisconsin. Fully accredited by the American Montessori Society (AMS), MSOW serves approximately 375 children from 18 months through 8th grade in a vibrant, child-centered community.

Rooted in authentic Montessori pedagogy, our mission is to foster each child’s potential and a lifelong love of learning. We are committed to nurturing curiosity, independence, and academic excellence within a supportive, family-friendly culture. Our dedicated team of educators and administrators works in close partnership with engaged families and a collaborative Board of Trustees.

MSOW also operates several unique programs that enrich its impact:

A Montessori Teacher Education Program (TEP), accredited by the Montessori Accreditation Council for Teacher Education (MACTE) and affiliated with AMS. The TEP prepares future Montessori educators under the strategic oversight of the Head of School.

A partnership with the local public school district that offers a tuition reimbursement program, significantly increasing accessibility for district families.

A well-attended summer program serving approximately 100 students, as well as wrap care offered during the academic year and summer months.

Learn more at www.msow.org and www.gmeinstitute.org.

Position Summary

The Head of School (HOS) serves as the Chief Executive Officer and educational leader of Montessori School of Waukesha. Appointed by and accountable to the Board of Trustees, the HOS is responsible for the overall strategic, operational, and cultural leadership of the school and its affiliated Montessori Teacher Education Program.

The HOS provides visionary direction, ensures operational excellence, and upholds MSOW’s Montessori mission across all program levels—from early childhood through middle school—while fostering collaboration among faculty, families, and the broader community. We are seeking a new Head of School to succeed our current Head, who is retiring in June.

Working with a seasoned leadership team, the HOS supervises the:

Director of Faculty and Staff (instructional leadership, employee supervision)

Director of Students (student life, assessment, special education)

Director of Accounting and HR (finance and operations)

Director of the Montessori Teacher Education Program

Key Responsibilities

Strategic & Executive Leadership

Serve as the Chief Executive Officer of the school, ensuring institutional health, growth, and alignment with mission and values.

Partner with the Board to develop and implement strategic plans and long-term vision.

Maintain transparency and mutual trust with the Board through regular communication and reporting.

Provide oversight of the Montessori Teacher Education Program, ensuring continued compliance with AMS and MACTE accreditation standards.

Educational & Instructional Leadership

Champion the Montessori philosophy, ensuring authenticity and program integrity across all age levels.

Collaborate with the Director of Faculty and Staff to support professional development, curriculum leadership, and instructional excellence.

Foster a culture of continuous improvement and shared accountability for student outcomes.

Organizational & Team Leadership

Lead, supervise, and evaluate the senior leadership team (Directors) with oversight over their areas of responsibility.

Build and sustain a positive, mission-driven culture grounded in respect, collaboration, and growth.

Promote an educational environment that is welcoming, equitable, and inclusive.

Financial & Operational Management

Oversee budgeting, financial planning, and resource management, ensuring sustainability and compliance.

Collaborate with the Director of Accounting and HR to maintain strong fiscal health and operational integrity.

Guide fundraising, donor relations, and grant-writing efforts in partnership with the Board and advancement committees.

Community Engagement & Advancement

Serve as the primary ambassador for MSOW, representing the school to families, donors, alumni, and the broader community.

Lead enrollment management, marketing, and outreach efforts to strengthen visibility and retention.

Communicate with authenticity, transparency, and consistency to all stakeholders.

How to Apply

Please submit the following materials to board@msow.org by January 31, 2026:

• Cover letter
• Resume
• Statement of educational philosophy
• Three professional references
• Complete the AMS Head Of School Verification (linked below)

https://docs.google.com/document/d/1tp1c4GmlazRFETIIbUhAruqAVFywZT1l-lZBTIeTkOU/edit?usp=sharing

Please email all the above requirements to board@msow.org