The Montessori School of Raleigh and Carolina Preparatory Academy, Head of School

Mossand Ross•Raleigh, NC

16d•Onsite

About The Position

The Head of School serves as chief executive and leader of the Montessori School of Raleigh (MSR) and Carolina Preparatory Academy, responsible for overall leadership, administration, and long-term strategic growth across both campuses. Reporting to the Board of Trustees, the Head leads approximately 100 faculty and staff serving more than 420 students, ages 15 months through grade 12. The Head will guide the schools through their next phase of development, building on the strengths of Montessori and International Baccalaureate education while fostering a cohesive educational pathway and community. In partnership with the Board, faculty, staff, families, and other stakeholders, the Head will honor each school’s distinct educational philosophy and culture, strengthen trust and organizational effectiveness, and guide strategic decisions about enrollment, institutional size and structure, educational programs, finances, and facilities. The role calls for a visible, relationship-centered leader with the strategic vision and judgment to translate priorities into measurable action, lead meaningful change, and support long-term sustainability. The Head will advance educational excellence, strengthen enrollment and retention, support faculty and staff, cultivate community engagement and philanthropy, and ensure effective operations, compliance, safety, and accountability. A bachelor’s degree is required; an advanced degree in education, leadership, or a related field is preferred. A Montessori credential or formal Montessori training is not required, but the ability to understand and champion Montessori philosophy is essential. Preference will be given to candidates with teaching or leadership experience in Montessori and/or International Baccalaureate settings.

Requirements

Bachelor’s degree required.
Significant educational leadership experience, including supervision and development of senior leaders and faculty.
Demonstrated experience partnering with a governing Board and fostering an effective Board–Head of School relationship.
Proven ability to assess organizational and market opportunities, translate strategic plans into measurable action, and guide complex decisions about institutional direction, growth, and sustainability.
Strong executive judgment and ability to navigate complexity, challenge assumptions, build consensus, and make thoughtful decisions while maintaining organizational trust.
Deep commitment to Montessori and International Baccalaureate educational philosophies, global citizenship, and educational excellence; ability to use outcomes and data to inform program development and continuous improvement.
Demonstrated success strengthening organizational structures, leadership teams, and operational systems that support accountability, collaboration, and institutional effectiveness.
Visible, approachable, authentic leadership presence and ability to build trusting relationships with faculty, staff, families, students, and the broader school community.
Exceptional communication and interpersonal skills, including active listening, transparency, conflict resolution, and engaging diverse perspectives.
High emotional intelligence, integrity, and sound judgment, with the ability to balance empathy and professional autonomy with accountability and decisive leadership.
Strong financial and business acumen, including budgeting, financial planning, resource allocation, and evaluating financial models for institutional sustainability.
Experience guiding enrollment, retention, and market-positioning strategies while balancing educational quality, accessibility, and financial priorities.
Experience supporting advancement and philanthropic efforts, including donor engagement and revenue diversification.
Respect for educators, the distinct cultures of MSR and Carolina Prep, and the relationships and traditions of both school communities.
Experience building an inclusive, diverse, collaborative, and supportive educational environment that values student growth, faculty excellence, and community engagement.
Ability to understand and champion Montessori philosophy; a Montessori credential or formal Montessori training is not required.

Nice To Haves

Advanced degree in education, leadership, or a related field.
Teaching and/or leadership experience in Montessori and/or International Baccalaureate settings.

Responsibilities

Partner with the Board of Trustees to advance the schools’ mission and strategic priorities, provide timely information and recommendations, and maintain clear distinctions between governance and management.
Advise the Board on strategic priorities and long-term planning; support Board development, committee effectiveness, transparency, accountability, and a productive Board–Head partnership.
Assess enrollment trends, competitive positioning, program strengths, and market opportunities, and lead strategic initiatives with clear priorities, measurable goals, and accountability.
Work with the Board and school leadership to evaluate future opportunities and determine the long-term direction, sustainable size, and structure of both schools.
Lead an enrollment strategy to attract, enroll, and retain a mission-aligned, diverse student body; establish realistic enrollment and retention goals aligned with program quality, capacity, and financial sustainability.
Improve student retention and family experience, and clearly communicate the value of the schools’ educational continuum.
Explore long-term growth opportunities, including potential program expansion or additional campus development.
Champion Montessori and International Baccalaureate education, maintaining program quality, academic rigor, and alignment with educational philosophies and accreditation or authorization standards.
Work with academic leaders and faculty to strengthen the educational continuum between MSR and Carolina Prep, support program evaluation and faculty excellence, and promote strong student outcomes and student-centered learning.
Promote an inclusive learning environment that recognizes diverse learning needs, supports appropriate interventions, and encourages collaboration among faculty, staff, and families.
Recruit, develop, support, and retain a talented and diverse faculty, staff, and leadership team through professional development, clear expectations, and respect for professional expertise and autonomy.
Strengthen organizational structures, leadership roles, communication practices, and decision-making systems across both campuses.
Foster transparency, respect, open communication, belonging, and trust while honoring the distinctive identities and traditions of each school.
Partner with enrollment and marketing leaders to strengthen brand positioning, communicate the schools’ educational value, and attract mission-aligned families.
Maintain a visible and accessible presence across both campuses and build relationships with students, families, faculty, alumni, and community partners.
Align budgets, resources, and investments with strategic priorities and long-term sustainability; strengthen financial planning and revenue diversification, including advancement and philanthropy.
Partner with the Board and leadership team to assess facility needs, capital investments, and responsible growth opportunities.
Ensure effective operations, sound policies, and administrative systems; oversee compliance, safety, risk management, and legal and regulatory responsibilities, and inform the Board of significant issues.
Establish clear expectations, performance measures, and accountability systems to support continuous improvement and measurable progress.