Assistant Director of Annual Giving

Staff / Full-Time

The Winsor School, Boston, MA

Reports to: Director of Annual Giving

Responsibilities Include:

Direct Marketing, Project Management, and Stewardship

  • With input from the Director of Annual Giving and Marketing and Communications team, lead in strategy development and management of annual giving appeals, direct marketing initiatives and communications, including managing internal and external deadlines, organizing input from key stakeholders and generating mail lists.
  • Serve as lead project manager for Giving Day strategy to broaden giving participation and engage peer to peer fundraising. Ensure execution and implementation of Giving Day goals.
  • Assist in stewardship of annual fund donors including the timely production of customized acknowledgement letters, donor recognition communications, and thanking donors by phone and email. Develop creative ideas for stewarding and cultivating donors in partnership with the Director and other Advancement colleagues.
  • Create and send electronic appeals and communications using Raiser’s Edge NXT.
  • Working with the Director of Annual Giving, oversee logistics for Annual Giving events such as committee meetings, faculty/staff giving celebration, and the annual leadership giving dinner.
  • Working with the Assistant Director of Advancement Services, prepare reports and presentations for the board, business office, board and volunteer committees, and other key stakeholders.
  • Track and prepare pledge reminders for AF, Campaign, and other gifts.

Volunteer Management

  • Work closely with the Director of Annual Giving to prepare for Annual Giving Committee meetings, organize agendas, create materials, and coordinate meeting follow up.
  • Execute volunteer recruitment and engagement strategy for annual giving alumnae and parent volunteers.
  • Create meaningful and educational materials to aid volunteers in successful relationship building and solicitations with their peers.
  • Coordinate annual volunteer briefing event.
  • Work with faculty and staff on employee fundraising efforts.

Campaign Operations and Research

  • With CAO, AF Director, and MG officers, provide operational support to the Campaign Working Group.
  • Lead overall campaign tracking effort (with AD of Advancement Services) and manage screening lists for donor solicitation and moves management for the campaign including the key nucleus phase of donor meetings, preparation of box charts and other key campaign materials working closely with the Campaign Director.
  • Conduct research on foundations, coordinate with gift officers to maintain foundation relationships, and write required proposals and reports.
  • Liaise with Admissions for new parent research; lead Admissions research and other donor research as needed.

General Department Support

  • Work with the Operations team to ensure appropriate planning and implementation of systems and strategies as related to the Annual Giving program, campaign, and other needs.
  • Assist in the operations and logistics for advancement events and ensure staffing needs are met.
  • Participate in appropriate team working groups to accomplish shared goals.
  • Partner with Assistant Director of Advancement Services and other colleagues as needed.
  • Provide exceptional collaboration strategy and customer service to all key stakeholders.


  • A bachelor’s degree.
  • 5+ years of development/fundraising experience; experience with Annual Giving preferred.
  • Demonstrated success with project management, direct marketing, and/or fundraising initiatives.
  • Proven experience or transferrable skills in digital marketing.
  • Talent for developing meaningful, genuine relationships through volunteer management.
  • Strong public speaking, presentation, and communication skills.
  • A thorough knowledge of Word, Excel, PowerPoint, and preferably Raiser’s Edge or equivalent CRM database.
  • Excellent organizational, analytical, time management, problem solving skills and attention to detail.
  • Ability to manage multiple projects successfully in a fast-paced environment.
  • Ability to work independently and as a member of a team.
  • A passion for Winsor’s mission and for the development profession. Keen understanding of Winsor’s mission and goals, and the ability to articulate the school’s uniqueness and relevance.


The Winsor School

Boston, MA
Elementary, Middle School, High School