Assistant Director of Alumnae 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 Alumnae Engagement is a liaison between a multi-generational alumnae community and Winsor, and is responsible for cultivating relationships to the School, coordinating alum volunteer opportunities, and building connections between alums and Winsor.

Alumnae Event Planning & Execution

  • Serve as a liaison between Winsor and alums to deepen connection to the school and build effective lines of communications.
  • Plan and execute alum events and programs as assigned, including regional and local alumnae cultivation events.
  • Assist the Director of Engagement and Events with the coordination, planning, and execution of programs and events related to alumnae engagement, including Winsor’s Tentpole Events: Alumnae Weekend and the annual meeting of The Winsor Corporation.
  • Increase Winsor’s reach by strengthening alumnae engagement program offerings.

Volunteer Management

  • Help to continually align Alumnae Board (AB) and Young Alumnae Council (YAC) priorities with school needs.
  • Communicate with volunteers to strengthen their involvement with Winsor and grow their philanthropic support.
  • Oversee the Young Alumnae Council and assist the Director of Engagement and Events with oversight of the Alumnae Board.
  • Liaise between the Alumnae Board, Young Alumnae Council, and the School.
  • Coordinate and organize AB and YAC meetings.
  • Amplify Winsor’s vision for diversity, equity, and inclusion to the entire community.

Alumnae Communications

  • In collaboration with Winsor’s Marketing and Communication team, coordinate, manage, and assist with communications pertaining to alum-related events and programs.
  • Curate story opportunities for the Winsor Bulletin, social media, and other platforms to amplify alumnae stories and news.
  • Participate in production of the Winsor Bulletin as an editor, reviewing content and fact-checking to help ensure accuracy.
  • Conduct surveys to collect and update alum information and data as needed.

General Operations

  • Collaborate with the Director of Annual Giving to grow alumnae participation in The Winsor Fund.
  • Help manage and track the budget for alumnae programs and 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 alumnae 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+ alum 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.

The Winsor School is an equal opportunity employer and will not discriminate against any application for employment on the basis of race, color, religion, gender, age, national origin, marital status, sexual orientation, genetic testing, veteran status, physical or mental disability, or on any other basis prohibited by law.

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

The hiring process includes:

  • Virtual interview with Becky Withiam, Director of Engagement and Events
  • Virtual or in-person 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

Contact Becky Withiam at


The Winsor School

Boston, MA
Elementary, Middle School, High School