Assistant Head of School for External Affairs

Reports to: Head of School

Supervises: Enrollment professional, Director of Marketing & Communications, and Development professional

Position Overview

The Assistant Head of School for External Affairs serves as a key member of the school’s senior leadership team and is responsible for advancing the school’s visibility, reputation, and resources through the thoughtful integration of marketing, enrollment, and development. Rooted in Montessori philosophy, this leader works to communicate and embody the school’s values of respect, curiosity, independence, and community. The Assistant Head of School for External Affairs develops and executes a strategic vision that connects families, alumni, past parents, and the broader community to the school’s mission.

This role requires both strategic foresight and hands-on engagement: the Assistant Head will guide planning and analysis while personally engaging in fundraising, donor relations, community partnerships, and enrollment initiatives that support the school’s mission and values. In addition, this position requires the experience, judgment, and leadership capacity to step into the Head of School role when needed, ensuring continuity of leadership and the smooth operation of the school in the Head’s absence.

Key Responsibilities

Leadership

• Capacity to step into the Head of School role when needed, ensuring continuity of leadership and smooth operation of the school in the Head’s absence.

Strategic Leadership

• Develop and implement a cohesive external affairs strategy that aligns marketing, enrollment, and development efforts with Montessori principles and the institution's long-term goals.
• Serve as a thought partner to the Head of School and Board, helping articulate a clear and compelling vision for the school’s future.
• Ensure that all outward-facing initiatives reflect the school’s Montessori values.
• Utilize data, research, and reflective practice to evaluate and refine strategies for community engagement, enrollment health, and philanthropy.

Marketing and Communications

• Partner with the Director of Marketing and Communications to lead mission-centered storytelling that highlights the distinct value of Montessori education and the Toddler–8th grade continuum.
• Oversee consistent, authentic communication across all platforms (print, digital, and social) that reflects Montessori tone and values.
• Support staff in communicating the Montessori approach to prospective families and the community.
• Collaborate with the Director of Marketing and Communications to curate the school’s public presence and community partnerships in a manner that fosters an understanding of Montessori education and enhances the school’s reputation.

Enrollment Management

• Partner with the Director of Enrollment to attract and retain families who align with Montessori philosophy and the school’s mission.
• Hone the pre-existing, thoughtful, relationship-based admissions practices that reflect Montessori values of respect and individualized attention.
• Analyze demographic and community trends to inform strategic enrollment decisions.
• Work with the Director of Enrollment to strategically allocate financial aid and tuition remission.

Development and Advancement

• Lead and participate in all aspects of development work, from strategy to direct donor engagement.
• Personally cultivate and solicit gifts to support school priorities.
• Partner with the Head of School and Board of Trustees to deepen philanthropic culture and build long-term sustainability.

Qualifications

• Bachelor’s degree: required; advanced degree preferred.
• Experience: At least 10+ years of progressively responsible experience in advancement in an independent or Montessori school setting.
• Enrollment strategy: At least 5+ years leading enrollment strategy.
• Management experience: At least 5+ years of management experience, including experience managing multiple constituencies – i.e., internal staff, families, donors, and other external parties.
• Success: Demonstrated success leading integrated external relations strategies.
• Relationship cultivation: Proven ability to cultivate relationships and secure major gifts.
• Skills: Outstanding communication, organizational, and interpersonal skills.
• Appreciation: Warmth, integrity, and a deep appreciation for Montessori education and its values.

Attributes and Competencies

• Strategic and reflective thinker with strong follow-through.
• Relationship-centered leader who models Montessori respect and empathy in all interactions.
• Skilled storyteller who can translate Montessori philosophy into accessible and inspiring language for a range of audiences.
• Collaborative and collegial; able to work effectively with educators, families, board members, and community partners.
• Committed to diversity, equity, justice, inclusion, and belonging as essential expressions of Montessori principles.