Executive Director

Sunny Hollow Montessori is growing! We are excited to welcome an Executive Director in the 2025-2026 school year.

POSITION SUMMARY:

The Executive Director (ED) at Sunny Hollow Montessori (SHM) is a senior leader responsible for advancing the school’s operational excellence, financial sustainability, external partnerships, and overall organizational health. In a co-leadership model with the Head of School, the ED will steward all non-pedagogical functions, enabling the Head of School to focus fully on educational leadership and internal community-building. Both roles report directly to the Board of Trustees and collaborate closely to align mission, strategy, and execution.

This role strengthens SHM’s leadership infrastructure in support of long-term growth and resilience. The Executive Director will lead operations, finance, development, marketing, compliance, HR infrastructure, facilities, and key strategic initiatives.

REQUIRED EDUCATION & EXPERIENCE:

• Bachelor’s degree in Business Administration, Nonprofit Management, or related field.


• Minimum 5 years experience in operational leadership, finance, or business management – preferably in education or nonprofit sectors.


• Proven success in managing budgets, compliance, HR systems, and team leadership.


• Experience with fundraising, donor stewardship, and grant writing.


• Experience working in a co-leadership or collaborative executive structure, preferred.

QUALIFICATIONS & COMPETENCIES

• Excellent interpersonal, written, and verbal communication skills.


• A passion for working in a school environment and a genuine appreciation for children and their families.


• High emotional intelligence, a collaborative mindset, and an ability to build trust across diverse stakeholders.


• Must be able to communicate effectively, both verbally and in writing, including in group settings or video conferencing.


• Knowledge of Montessori education or progressive school environments, preferred.


• Demonstrated commitment to diversity, equity, and inclusion in leadership practices, preferred.

ESSENTIAL DUTIES AND RESPONSIBILITIES:

Program & Pedagogy

• Develops and maintains operational systems that support the delivery of high-quality educational programs.


• Ensures all operational functions are aligned with and uphold the mission of Sunny Hollow Montessori

Culture & Staff

• Oversees the school’s HR infrastructure and operational staffing needs, with a focus on building a strong and sustainable staff retention strategy.


• Leads the recruitment, hiring, and onboarding of administrative and operational staff.

Union & Labor

• Manages relationships with legal counsel and oversees all bargaining logistics and HR compliance.


• Serves as the primary liaison for legal processes related to union negotiations.


• Collaborates with the Head of School to co-lead efforts to build trust with union and non-union staff.

Operations & Compliance

• Provides direct oversight of all operational functions, including budgeting, payroll, insurance, facilities, technology, legal compliance, and landlord relations.

Board & Strategic Planning

• Leads all financial and operational reporting to the Board of Trustees.


• Partners with the Board on strategic initiatives and governance systems, including Board onboarding and offboarding.


• Actively supports the pedagogical vision of the Head of School through aligned operational planning.

Family  & Community Engagement

• Designs and maintains systems and infrastructure that support strong parent communication, engagement, and community connection.

Marketing & Admissions

• Oversees enrollment strategy, data systems, and marketing efforts to ensure a strong admissions pipeline and effective outreach initiatives.

PHYSICAL REQUIREMENTS

• Prolonged periods sitting at a desk and working on a computer.


• Ability to occasionally move about the school, including navigating stairs and walking throughout the building.


• Must be able to lift up to 20 pounds occasionally.


• Must be able to communicate effectively, both verbally and in writing, including group settings or video conferencing.

MANAGES:

• Marketing/Engagement Director


• School Caretaker


• Office Manager
  

WORK ENVIRONMENT:

The Executive Director works in a dynamic, mission-driven school setting that requires both strategic focus and day-to-day operational oversight. This position is primarily office-based, with frequent movement throughout the school campus to collaborate with staff, attend meetings, and support on-site initiatives. The role involves extended periods of computer and desk work, balanced with in-person engagement across departments and functions. The Executive Director must be comfortable navigating a multi-level school building and participating in school-wide activities as needed. While the position is not physically strenuous, it requires high levels of organization, responsiveness, and relational leadership. Occasional evening and weekend hours are required for Board meetings, community events, and strategic planning sessions. This is a full-time, on-site position; remote work is not available.

Sunny Hollow Montessori is an affirmative action and equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, gender expression, national origin, age, protected veteran or disabled status, or genetic information. Please visit our website at Welcome to Sunny Hollow Montessori | Guiding children from infancy to adulthood