Job Overview:

The Director of Alumni & Community Engagement is responsible for developing and implementing a comprehensive strategy to strengthen lifelong relationships between Stephen Gaynor School and its alumni, alumni families, and broader school community. Working closely with the Director of Institutional Advancement, this position will build a robust alumni engagement program that cultivates meaningful connections, identifies and stewards major gift prospects, expands alumni philanthropy, and establishes a foundation of prospects for a planned giving program that supports the long-term financial strength of the School.

The Director will develop opportunities for alumni to remain engaged through volunteer leadership, networking, mentorship, and community-building initiatives while fostering a culture of giving among alumni and alumni parents. In addition, the Director will support key community engagement initiatives, including faculty and staff appreciation activities, commencement, and relationship-building with current blue cluster families as they progress through the Gaynor experience.

Stephen Gaynor School offers a competitive compensation package and a comprehensive professional development program. Applicants are required to submit a resume, cover letter and contact details for at least two individuals who can supply reference letters upon appointment.

Please apply online at Employment Opportunities.

THE GAYNOR DIFFERENCE: UNLOCKING EACH STUDENT’S POTENTIAL

Since 1962, Stephen Gaynor School has been redefining what’s possible for children with learning differences. Located on Manhattan’s Upper West Side, Gaynor provides an individualized, evidence-based education for students in Pre-K through 8th grade who learn differently, including those with dyslexia, dysgraphia, dyscalculia, and ADHD.

At Gaynor, our nearly 400 students benefit from small classes, a 3:1 student–teacher ratio, and specialized instruction, ensuring every child receives the support they need to thrive. Faculty work side by side with in-house specialists in speech, occupational therapy, literacy, and psychology— integrating academic, emotional, and developmental growth into every student’s experience.

Beyond academics, Gaynor emphasizes confidence, self-advocacy, and belonging. Students learn to understand how they learn best, communicate effectively, and take pride in their progress. The school’s joyful, inclusive community celebrates diversity and nurtures each child’s curiosity and creativity, ensuring they feel valued and supported at every step.

Graduates leave Gaynor with a strong foundation—academically prepared, emotionally grounded, and equipped with the tools to navigate new challenges. Families describe the experience as transformative: a place where children are understood, empowered, and inspired to reach their fullest potential.

Our Diversity Mission: Stephen Gaynor School is dedicated to promoting and advocating for diversity, equity, and inclusion within our school community. We recognize, value, and celebrate many types of diversity, including neurodiversity, ethnicity, race, socioeconomic status, ability, religion, sexual orientation, family composition, language, and gender identity/expression.

Equal Employment Opportunity Statement: Stephen Gaynor School is an equal employment opportunity employer. Gaynor is committed to building a culturally diverse and anti-racist workforce. We provide opportunities for employment without discrimination or harassment on the basis of (including hairstyle), color, religion, creed, ancestry, sex, sexual orientation, gender and gender identity, gender expression, national origin, alienage, age, pregnancy, marital/partnership status, immigration or citizenship status, status as a veteran or active military service member status, disability, genetic predisposition, status as a victim of domestic violence, prior arrest or conviction record, caregiver status, credit history, salary history, unemployment status, sexual or reproductive health decisions, or any other characteristic or status protected by applicable law (collectively, the “Protected Characteristics”).