Executive Assistant to Head of School

A leading independent Pre-K–12 school in New York City is seeking an

Executive Assistant

to support the Head of School. With a diverse student body from over 100 zip codes, the school thrives on collaboration and a deep commitment to belonging. The culture emphasizes a student-centered approach, open-mindedness, and a shared passion for positive impact. This role is essential in ensuring smooth leadership operations and meaningful engagement across the school community.

Who You Are

A proactive and highly organized Executive Assistant with a bachelor's degree and at least 5 years of experience supporting senior leaders

A natural relationship builder who communicates with clarity, discretion, and warmth across all levels of an organization

A strategic thinker who thrives on managing complex calendars, coordinating high-stakes meetings, and keeping priorities aligned

Comfortable handling sensitive information and navigating confidential matters with professionalism and care

Some exposure to Human Resources processes, highly preferred

What You'll Do

Serve as the right hand to the Head of School, managing day-to-day operations and acting as a key liaison across departments

Coordinate and track strategic initiatives, ensuring timely progress and alignment with institutional goals

Manage a dynamic calendar, schedule meetings and events, and prepare materials for internal and external engagements

Draft and edit high-level communications, reports, and presentations with precision and polish

Organize and support leadership and board meetings, including logistics, agendas, and follow-up documentation

Oversee the preparation and processing of confidential documents, including employment contracts, in collaboration with HR and Finance

Maintain organized systems for records, policies, and governance materials

Support the planning and execution of major school events and leadership retreats

What Success Looks Like

The Head of School's office runs smoothly, with clear priorities, seamless scheduling, and proactive communication

Strategic projects move forward efficiently, with strong coordination and timely follow-through

Leadership and board meetings are well-organized, with clear agendas, accurate documentation, and effective outcomes

Confidential documents are handled with care, accuracy, and compliance

Cross-campus collaboration is strengthened through thoughtful communication and coordination

You are seen as a trusted partner, problem-solver, and steady presence in a dynamic school environment

Salary Range :

$120,000 – 140,000 annually, based on experience

Gainor is committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions at Gainor are based on business needs, job requirements and individual qualifications, without regard to race, color, religion, creed, sex, sexual orientation, gender (including gender identity and expression), age, national origin, immigration status, marital or familial status, citizenship status, ancestry, physical or mental disability, genetic information, reproductive health decision making, veteran or military status, or any other characteristic or status protected under applicable federal, state, or local law.

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