Assistant Director of Alumnae Engagement and Leadership Giving
  • Advancement

The Winsor School, Boston, MA

Accredited by NEASC

Founded in 1886, The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Since its founding the School grew quickly and today students benefit from its commitment to providing a superior education for girls, inspirational and dedicated faculty, and a 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 more inclusive curriculum, success addressing a range of learning styles, the availability of a wide array of diversity efforts and programs, and by participating in the greater Boston community.

Winsor seeks an energetic Assistant Director with fundraising experience to join a dynamic team. This position works closely with the Director of Alumnae Engagement to plan, organize, and execute logistics for alumnae programming. The Assistant Director acts as a liaison for the Young Alumnae Committee and assists the Operations team with administrative support for general advancement operations.

Reports to:    Director of Alumnae Engagement


Alumnae Engagement

  • Support the Director in all aspects of planning, organizing and executing programming and events for 3100 alumnae.
  • In collaboration with the Director and the Communications team assist with writing and editing all alumnae communications including the school magazine.

Volunteer Management

  • Liaison to the Young Alumnae Committee and supports the Chairs of the committee.
  • Work with Alumnae Association volunteers on assigned projects.
  • Engage volunteers in a variety of roles, including identification, cultivation, solicitation, stewardship, and events.


  • In collaboration with the Director of Alumnae Engagement, the Director of Annual Giving and the Chief Advancement Officer, the Assistant Director will assist with young alumnae donors and will have direct responsibility for a portfolio of prospects, including young alumnae and leadership level donors.
  • Ensure that key prospects are actively managed with regular face-to-face meetings and outreach with prospects to communicate campaign and annual goals and priorities and move prospects along the donor pipeline.
  • Prepare and present written and oral briefings, follow-up materials, and contact reports on prospects/donors in a timely manner.
  • Write, edit, and proofread proposals, letters, and other correspondence.
  • Work collaboratively with Advancement staff to devise and recommend cultivation and solicitation strategies; serve as a resource for staff and volunteers.
  • Acknowledge personally all gifts from assigned prospects.
  • Meet quarterly benchmarks and goals based on activity with prospects/donors and annual fundraising goals.
  • Assist with stewardship/cultivation as assigned.


  • With the Advancement Operations Team, ensure appropriate planning and implementation of systems and strategies to support the work of the department
  • Other duties as assigned


  • A Bachelor’s degree. 5+ years of experience in an office setting in a non-profit administration or an independent school environment with fundraising experience.
  • Deep commitment to independent school education.
  • Keen understanding of Winsor’s mission and goals, and the ability to articulate the School’s uniqueness and relevance.
  • Strong organizational and time management skills with exceptional attention to detail.
  • Excellent communication skills, both verbal and written, with a strong ability to influence and engage a wide range of donors and build long-term relationships.
  • Demonstrated maturity and highest level of integrity, discretion, and respect for donor confidentiality and handling of sensitive information, tasks, and relationships.
  • Skill in proofreading and editing, attention to detail, and follow-through. Computer literacy, particularly in Microsoft Office Suite, PowerPoint, using internet resources, and relational databases, such as Raiser’s Edge or equivalent required. Comfort with online fundraising and social media.
  • Some travel and weekend and after-hours work required.
  • Ability to manage multiple projects successfully in a fast-paced environment.
  • Ability to take initiative when appropriate and to succeed in a collaborative team environment.
  • A sense of humor is appreciated.

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.

Please visit the Winsor Careers page to submit your resume and a cover letter: