Director of Engagement and Events

Staff / Full-Time

The Winsor School, Boston, MA

The goal of the Engagement team is to build an inclusive and connected community across generations. Partnering with the Alumnae Association Board and the Parent Association, and their related subcommittees, the Engagement program provides opportunities for alumnae, parents, former parents, and friends of Winsor to connect with the school and each other to broaden their understanding of Winsor’s mission and needs.The Director of Engagement & Events’ responsibilities focus on the strategic planning, communication, and implementation of an array of comprehensive engagement programs and events that facilitate the development of informed and involved alumnae and parents.

Reports to: Director of Advancement

Engagement Management

  • Determine and develop the vision for all engagement experiences relative to alumnae, past parent, and current parent constituent groups.
  • Build, steward, and cultivate relationships within the Winsor community.
  • Manage and oversee the Assistant Director of Alumnae Engagement and the Assistant Director of Parent Engagement.
  • In partnership with the Marketing & Communications team, connect, cultivate, and effectively communicate to the Winsor community through print, web, the alumnae phone application, and social media.

Event Planning & Execution

  • Provide strategic planning and strong leadership for all engagement programs and events.
  • Increase Winsor’s geographic and demographic reach by innovating and reinvigorating the engagement program offerings.
  • Serve as the lead/co-lead and coordinate, plan, and execute programming and events for engagement functions, including Winsor’s Tentpole Events: Alumnae Weekend, Benefactor’s Dinner, Winsor Associates’ Dinner, Trustee/Faculty/Staff Dinner, Parents of Alumnae event, and the annual meeting of the Winsor Corporation.
  • Position and empower the Assistant Director of Alumnae Engagement and the Assistant Director of Family Engagement to take responsibility for the logistics and execution of all alumnae and family events, such as Young Alumnae Committee events, Grandparent and Grandfriend stewardship events, and New Families Welcome events.
  • In partnership with the Director of Annual and Leadership Giving, manage the strategic planning for Reunion classes and alumnae volunteer teams for each reunion class.
  • Communicate with volunteers regularly to strengthen their involvement with Winsor and grow their philanthropic support of the school.

Parent, Alumnae & School Relations

  • Manage and support the Alumnae Board. Work with the President of the Alumnae Association Board on the vision and strategy for the AAB, attending Alumnae Association Board Meetings.
  • Oversee the Assistant Director of Alumnae Engagement as they manage the committees associated with the Board.
  • Oversee the Assistant Director of Parent Engagement as they manage the Parent Association (PA) and other volunteer programs and activities associated with the PA and Winsor parent community.
  • Develop a strategy to align PA priorities with the School’s needs, particularly The Winsor Fund, and ensure messaging and communication highlights the value of participatory gifts and the investment of volunteer time.
  • Amplify Winsor’s vision for diversity, equity, and inclusion to the entire community.

Advancement Responsibilities

  • Ensure relationships are developed with alumnae and families through engagement tactics that complement fundraising activities.
  • Liaise with the fundraising team to align engagement activities with the moves management practices.
  • Collaborate with the Fundraising team to help identify key prospects, build the pipeline, and ensure the fundraising team is aware of demographic and personal information related to Winsor constituencies.
  • Identify speakers for keynote presentations and panels.
  • Attend Advancement Committee meetings as needed.

General Operations

  • Maintain fiscal oversight of the Engagement budget, which includes parents, families, and alumnae budgets for 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 5 to 7 years of engagement, event, and volunteer management experience.
  • The ability to serve as senior member of the Advancement Team, providing thoughtful insights and high-level strategic input in all areas of engagement and event planning.
  • A working knowledge of constituent management systems with an emphasis in Raiser’s Edge for Windows, NXT, and Microsoft Windows suite of products.
  • Experience managing multiple direct reports, providing them with direction, feedback, and support.
  • This is a high visibility position in the Winsor Community which requires a solution-oriented mindset and strong skills in diplomacy, communication, collaboration, demonstrated sensitivity in handling confidential information, and a sense of humor.


  • Salary commensurate with experience.
  • This is a full-time, benefits eligible position.
  • 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 at:

This position will be open for applications until August 1, 2022, or until filled.

Hiring Process:

  • 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
  • Virtual or in-person interview with select members of the Board of Trustees. Desired start date for this position is on or before September 1, 2022.

 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