Director of Alumni and Community Engagement

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.

Essential Functions

Alumni Engagement

• Implement a comprehensive and evolving strategic plan for alumni engagement designed to strengthen lifelong relationships with Stephen Gaynor School.
• Develop and execute a multi-year alumni engagement strategy aligned with the School's advancement priorities.
• Build meaningful relationships with alumni across all graduating classes.
• Develop initiatives that increase alumni participation, volunteerism, and philanthropic support.
• Identify, qualify, and cultivate alumni and alumni parent major gift prospects.
• Partner with the Director of Institutional Advancement to develop individualized cultivation and solicitation strategies.
• Establish a planned giving program targeted to alumni and alumni families.
• Develop strategies to increase alumni participation in the Annual Fund.
• Create meaningful stewardship opportunities that recognize and celebrate alumni generosity.
• Expand alumni communications through newsletters, social media, digital storytelling, and targeted outreach.
• Develop regional and virtual alumni engagement opportunities.
• Recruit, train, and manage alumni volunteers and advisory committees.
• Develop alumni affinity groups and professional networking opportunities.
• Create mentorship opportunities connecting alumni with current students and recent graduates.
• Build internship and career networking opportunities for Gaynor students through alumni partnerships.
• Maintain accurate alumni records and engagement metrics within the school's database.
• Analyze participation, giving trends, and engagement data to continually strengthen programming.
• Collaborate with Admissions, Communications, and Academic Leadership to ensure alumni remain connected to the life of the School.

Community Engagement

• Coordinate and support Faculty and Staff Appreciation Week activities.
• Assist in planning and executing Gaynor's Graduation and Commencement activities.
• Serve as the Advancement Office liaison to Dark Blue Cluster families, helping to manage a graduation gift campaign, and developing meaningful relationships with parents as they enter the final year of their Gaynor experience.
• Develop engagement opportunities that help prepare current families for future alumni involvement and philanthropy.
• Partner with parent volunteers and school leadership on selected community-building initiatives.

Advancement Collaboration

• Collaborate with colleagues on Annual Fund, major gifts, stewardship, and campaign initiatives.
• Assist with donor cultivation events and alumni-focused fundraising opportunities.
• Support Advancement communications and storytelling efforts highlighting alumni impact.
• Represent the Advancement Office at school events, alumni programs, and community activities.
• Participate in departmental planning and strategic initiatives.
• Support advancement with parent events and donor recognition, cultivation and stewardship events.

Additional Duties

• Attend full faculty and staff meetings
• Willing to commit to anti-bias and anti-racism work and to promoting inclusion, belonging and equity through their work in the classroom and school community. 
• Ensure a commitment to the school’s DEI mission and goals by participating in continuous professional development for learning differences, anti-racism and anti-bias of all kinds.
• Be an active member of the Gaynor community
• Other duties and responsibilities as deemed appropriate

Qualifications

Qualifications & Skills:

• Bachelor's Degree required, Masters degree preferred
• Three to five years of development experience, preferably with a background in an educational alumni capacity
• Strong understanding of alumni relations, annual giving, special events, and constituent relations
• Event management and volunteer management experience
• Experience in an independent school or mission-driven nonprofit setting is preferred.
• Exceptional communication and interpersonal skills with the ability to build trust and rapport across diverse communities, including internal leadership and staff, families and outside professionals
• High proficiency with Microsoft Office and Google Workspace
• Exceptional customer service and database system configuration skills (Veracross experience preferred)
• Highly organized and resourceful with sound judgment and a results-oriented mindset.
• A strong commitment to diversity, equity, and inclusion and a passion for the mission of Stephen Gaynor School.
• Project Management Experience
• A commitment to creating and maintaining an inclusive and diverse community.
• Detailed-oriented with strong time management skills
• Ability to work independently
• Self-motivated, flexible, and able to work as part of a team
• Organized with the ability to multitask
• Must be thoughtful in approach to speaking to children with special needs
• Must be able to maintain confidentiality

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 atEmployment 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 within-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”).