Assistant Director of Family Engagement

Staff / Full-Time

The Winsor School, Boston, MA


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.


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.


  • 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.


This full-time, benefits-eligible position offers a salary commensurate with experience and the opportunity to work in a school environment and make an impact.


Please visit the Winsor Careers page to apply for and submit your resume and cover letter explaining why you are interested in this role and what you will bring to the position at by October 17, 2022.

The hiring process includes:

  • Virtual interview with Erika McMahon, Director of Advancement
  • Virtual or in-person meeting with Advancement Team Members
  • Virtual or in-person interview with Sarah Pelmas, Head of School

Desired start date for this position is on or before November 7, 2022.

Questions? Contact Erika McMahon at

Winsor is committed to building a diverse and inclusive campus community. We welcome applications from underrepresented groups.

The Winsor School

Boston, MA
Elementary, Middle School, High School