Head of School

Head of School (Chief Executive Officer)

Montessori School of Waukesha, Inc. — Waukesha, Wisconsin

Start Date:

June 1, 2026 (ideally sooner)

Final date to receive applications:
February 1, 2026

Reports to:

Board of Trustees

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.

MSOW also operates several unique programs that enrich its impact, including a Montessori Teacher Education Program (TEP) accredited by the Montessori Accreditation Council for Teacher Education (MACTE) and affiliated with AMS, a partnership with the local public school district offering tuition reimbursement for district families, and a well‑attended summer program serving approximately 100 students (plus wrap‑care during the academic year and summer).

Learn more w.org and (Use the "Apply for this Job" box below)..

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.

• 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 a 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.

• 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.

• 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.

• 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.

• 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.

Please submit the following materials to board by January 31, 2026:

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

Please email all the above requirements to board.

For full position details, please visit our website and submit your application materials: https://%20school

• Bachelor’s degree required.
• Minimum of three years of experience as a Montessori lead teacher post‑credential and demonstrated leadership experience in an educational setting.
• Proven executive or senior management experience in an educational or nonprofit organization.
• Strong understanding of and commitment to Montessori philosophy and practice.
• Demonstrated experience with strategic planning, budgeting, and organizational leadership.
• Excellent communication, interpersonal, and team‑building skills.
• Demonstrated ability to collaborate with a Board of Trustees or governing body.

• Master’s degree in Education, Organizational Leadership, Nonprofit Management, or a related field.
• AMS or AMI Montessori credential (administrator or teacher).
• Experience with teacher education programs or adult learning organizations.
• Fundraising and development experience, including grant writing and donor relations.