Executive Director

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

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.

• 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.

• 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.

• 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.

• 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.

• 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.

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

• 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.

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

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

• 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.

• School Caretaker
• Marketing, HR, and Accounting contractors

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…