Director of Annual and Leadership Giving

Posted on 02/05/2021

The Winsor School

Boston, Ma

Winsor seeks a Director of Annual and Leadership Giving to join a dynamic advancement team at an exciting time in the school’s history. The Director is responsible for the development of a comprehensive Annual Giving program, which reaches $3M+ each year and is poised for growth, in support of our mission. S/he is a strategic thinker who will help launch new initiatives and lead the program to new heights. The Director will work closely with high-level volunteer committees and school leadership to ensure that goals are met. The Director will have a portfolio of leadership and annual donors. S/he works closely with the Advancement Operations Team, manages an Assistant Director, and reports to the Chief Advancement Officer.

Responsibilities Include:

Direct Marketing and Annual Fund

  • With support from the Assistant Director of Annual Giving, plan and execute strategies to set and achieve Annual Giving goals.
  • Manage and advise the Assistant Director of Annual Giving’s leadership role in direct marketing and annual giving strategies.
  • Collaborate with colleagues to integrate Annual Giving, reunion giving, and major gift solicitation strategies.
  • Serve as a resource for fundraising staff and volunteers.
  • With the AD, drive the development of a communications plan for effectively marketing, messaging, segmenting, and executing appeals in collaboration with the Communications department.
  • Oversee the Assistant Director of Annual Giving’s work with Communications, and the AD’s work as the project manager and lead for annual appeals, appeals communications calendar, managing internal and external deadlines and organizing input from key stakeholders.
  • Working with the Database Manager/Assistant Director of Advancement Services and the AD, help prepare reports and presentations for the board, business office, advancement committee, finance committee and other key stakeholders

Volunteer Management

  • Lead the Annual Giving Committee and other high-level volunteers with support from the Assistant Director of Annual Giving.
  • Work closely with the Assistant Director of Annual Giving, prepare for Annual Giving Committee meetings, organize agendas, create materials, and coordinate meeting follow up.
  • Oversee and support the AD’s volunteer recruitment and management for alumnae and parent volunteer programs, and serve as point person for all AG volunteer activities with the AD.
  • Provide high-level volunteer support to the Board Chair, Annual Giving Committee Chair and others, including managing their assignments and staffing meetings.
  • In collaboration with the CAO, provide critical support and staffing for the Board of Trustees, the Corporation, and the Advancement Committee.

Portfolio Management and Fundraising

  • Grow and manage a portfolio of leadership and annual giving prospects at the $2,500 to $100,000 Winsor Associates levels.
  • Cultivate, solicit, and steward donors with focus on relationship building and growing the philanthropic support for the school.
  • Ensure that key prospects are actively managed with regular face-to-face meetings and outreach with prospects to communicate annual and campaign goals and move prospects along the pipeline.
  • Prepare and present written and oral briefings, follow-up materials, and contact reports on prospects/donors in a timely manner.
  • Represent the School at alumnae, parent, and other constituent events.
  • Work strategically, as assigned, with the CAO, Head of School, other senior administrators, faculty, staff, and volunteer leaders to support fundraising priorities.
  • Acknowledge personally all gifts from assigned prospects.
  • Visit specified regions across the country to cultivate prospective donors, staff senior administrators at events, and coordinate logistics for strategic visits.
  • Provide strategic and operational support as needed to the Campaign Working Group

Events and General

  • Working with the Assistant Director of Annual Giving, oversee logistics for Annual Giving events such as committee meetings, faculty/staff giving celebration, and the annual leadership giving dinner.
  • Work with the Operations team to ensure appropriate planning and implementation of systems and strategies as related to the Annual Giving program.


  • A bachelor’s degree.
  • 5+ years of development/fundraising experience; experience with Annual Giving and frontline fundraising preferred.
  • Demonstrated success managing professional staff and volunteers.
  • Talent for developing meaningful, genuine relationships.
  • Proven track record of soliciting and closing gifts of $10,000 or more.
  • Strong public speaking, presentation, and communication skills.
  • A thorough knowledge of Word, Excel, PowerPoint, and 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.

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