Assistant Director of Family Engagement

The Winsor School
Boston, MA

Founded in 1886, The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Located in the heart of Boston’s Longwood Medical and Academic Research area, our students benefit from the school's longstanding commitment to providing a superior education for girls, inspirational and dedicated faculty, and diverse and talented community. Winsor strives to consciously create an environment of respect and inclusion and to support ethnic, racial, religious and socio-economic diversity among all the constituencies of the school. Winsor supports this commitment through its inclusive curriculum, success addressing a range of learning styles, availability of a wide array of diversity efforts and programs, and participating in the greater Boston community.




Job Description: Assistant Director of Family Engagement
Position: Assistant Director of Family Engagement

Reports to: Director of Engagement and Events

Department: Advancement

Classification: Exempt, 12-month

POSITION SUMMARY

Winsor’s engagement team seeks to build an inclusive and connected community across generations, providing opportunities for alumnae, parents, former parents, and friends of Winsor to connect with the school and each other, and to broaden their understanding of Winsor’s mission and needs. The engagement team’s efforts help to inspire and grow philanthropic contributions to the School. Reporting to the Director of Engagement and Events, the Assistant Director of Family Engagement is a liaison between current parents, past parents, grandparents, and Winsor, and is responsible for orienting new families to the School, coordinating parent volunteer opportunities, and building connections between families and Winsor.

RESPONSIBILITIES

Family Event Planning & Execution

  • Serve as a liaison between Winsor and families to create a successful parent-school partnership and effective lines of communications.

  • Plan and execute parent and family events and programs as assigned, including Grandparent and Grandfriend stewardship events, New Families Welcome events, and Parents of Alumnae events.

  • Assist the Director of Engagement and Events with the coordination, planning, and execution of programs and events related to family engagement, including Winsor’s Tentpole Events: Benefactor’s Dinner, Winsor Associate’s Dinner, and the annual meeting of The Winsor Corporation.

  • Increase Winsor’s reach by strengthening family engagement program offerings.

Volunteer Management

  • Help develop a strategy to align PA priorities with school needs.

  • Communicate with volunteers to strengthen their involvement with Winsor and grow their philanthropic support.

  • Oversee the Parents’ Association and all volunteer programs and activities for parents.

  • Liaise between the Parents’ Association, Parents for an Inclusive Community (PIC), and the School.

  • Coordinate and organize Parents of Alumnae Committee and meetings.

  • Amplify Winsor’s vision for diversity, equity, and inclusion to the entire community.

Family Communications

  • In collaboration with Winsor’s Marketing and Communication team, coordinate, manage, and assist with communications pertaining to parents and family-related events and programs.

  • Ensure parents of alumnae, grandparents, and other family constituencies remain connected and engaged with Winsor.

  • Conduct surveys to collect new and current families’ information as needed.

General Operations

  • Collaborate with the Director of Annual Giving to grow parent participation in The Winsor Fund.

  • Help manage and track the budget for all parent and family programs or events.

  • Engage with the Winsor community beyond Advancement initiatives in order to represent the school authentically.

  • Be an active member of the broader Winsor community.

EXPERIENCE, KNOWLEDGE, AND SKILLS

  • A belief in all-girls independent school education, keen understanding of Winsor’s mission and goals, and the ability to articulate its uniqueness and relevance.

  • A bachelor’s degree with a minimum of 3 to 5 years of engagement, event, and volunteer management experience. A working knowledge of constituent management systems with an emphasis in Raiser's Edge for Windows, NXT, and Microsoft Windows suite of products.

  • Ability to build trust and garner respect from the parent community and encourage others to be involved and feel like a part of the Winsor community.

  • Leadership skills sufficient to organize, support, and direct 80+ parent volunteers.

  • A solution-oriented mindset, a demonstrated sensitivity in handling confidential information, strong skills in diplomacy, communication, collaboration, and a sense of humor.

  • Some travel and weekend and after-hours work required.

Work Environment and Physical Demands

Frequent talking, listening, walking, sitting and standing

Ability to perform multiple concurrent tasks and function in a fast-paced working environment

The employee must frequently lift and/or move up to 30 pounds


Compensation and Benefits
This is a full-time, benefits-eligible position with an anticipated salary range of $70,000–$90,000 , commensurate with experience and qualifications. The role also offers the opportunity to work in a mission-driven school environment and make a meaningful impact.

Posted 2026-08-10

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