Assistant Director of Alumni Giving & Engagement

Middlesex School seeks an Assistant Director of Alumni Giving & Engagement to cultivate relationships with young alumni and build a strong pipeline of annual donors in support of the school’s mission. Reporting to the Director of Development, the Assistant Director will work collaboratively with the Annual Giving team to secure support for the Middlesex Annual Fund from graduates of the last 15 years. This role focuses on identifying, cultivating, soliciting, and stewarding these donors, with an emphasis on recent graduates.

The Assistant Director will support Alumni Relations to advance a comprehensive alumni engagement strategy. Responsibilities include managing class giving for reunion years, coordinating young alumni events (college dinners, summer gatherings, networking nights), and working with key volunteer groups. This role creates targeted strategies and programming to engage young alumni personally through on-campus, local and regional events and via digital communications.

The ideal candidate will have a bachelor’s degree and 1-2 years of experience in development, alumni relations, or volunteer/event management, preferable in an educational or nonprofit setting. Strong interpersonal, organizational, and communication skills are essential. Comfort with solicitation, a passion for relationship building, and a commitment to Middlesex’s mission and values are key. This position requires occasional travel and the ability to thrive in a fast-paced, collaborative environment.

This is a full-time faculty position with growth potential. As a residential school, Middlesex faculty are deeply involved in the life of the school. In addition to development responsibilities, this faculty member will coach one season, advise a small group of students, attend faculty meetings, and participate in residential life through evening and weekend duty rotations. 

Middlesex School is committed to building a diverse and inclusive community. We value the contributions of candidates who can help us sustain and grow a vibrant school environment that reflects a broad range of identities and perspectives. 

Because Middlesex School is a residential boarding school, this role may be housed on campus or be eligible for a $20,000 engagement stipend for those not housed on campus.