Director of Annual Giving

Company: Winsor School
Location: Boston
Posted on: May 6, 2025

Job Description:

Founded in 1886, The Winsor School is an independent girls' school for academically promising and motivated students in grades five through twelve. Located in the heart of Boston's Longwood Medical and Academic Research area, our studentsbenefit from the school's long standing commitment to providing a superior education for girls, inspirational and dedicated faculty, and a diverse and 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.




Director of Annual GivingPosition Summary:The Winsor School, founded in 1886, is one of the nation's leading independent schools for girls and young women with an enrollment of 470 students in Grades 5-12. Located in the heart of Boston's Longwood Medical and Academic Research area, The Winsor School is a diverse, vibrant community that values intellectual curiosity, authentic engagement, and personal integrity. We challenge our students to lead lives of purpose as responsible, generous-minded women and join the broader community of faculty, staff, alumnae, and friends who share and support this mission. To support and promote Winsor's longstanding commitment to community and inclusion.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 $3.5M+ 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 Director of Events and Engagement, manage an Assistant Director of Annual Giving, and report to the Chief Advancement Officer.Reports to: Chief Advancement OfficerResponsibilities Include:Direct Marketing and Annual Fund

• With support from the Assistant Director of Annual Giving, plan and execute strategies to set and achieve ambitious 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.
• With guidance from the CAO, prepare reports and presentations for the Board of Trustees, Advancement Committee, Finance Committee, Campaign Co-chairs, 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 President of the Winsor Board of Trustees, Annual Giving Committee Chair, and other key volunteers, including managing their assignments and staffing meetings.
  • In collaboration with the CAO, provide critical support and staffing for the Head of School, Board of Trustees, and Annual Giving volunteers.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 DOD, 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 groupEvents 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.Qualifications:
            • 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.Please visit the Winsor Careers page to apply for and submit your resume and cover letter:https://www.winsor.edu/about/careers-at-winsor/
              
              The Winsor School is an equal opportunity employer and will not discriminate against any applicant 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 protected by law.Department: Administration
              This is a full time position
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              Attachments* Attach your Resume Attach Dropbox Paste * Attach a Cover letter Attach Dropbox Creative portfolio (writing/video/photo) Attach DropboxOther Information* Can you show proof of your legal right to work in the United States? Yes No * Do you now, or will you in the future, require our sponsorship for employment-based visa status? Yes No How did you hear about this position? * How many years of experience do you have in an educational or non-profit setting? What is your highest level of completed education? Do you have a current or prior relationship with The Winsor School? If yes, please indicate the nature of that relationship and relevant dates. Please list the different software programs, databases, and other technical skills you are proficient in. Social Media Platforms Blackbaud MS Office
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Keywords: Winsor School, Plymouth , Director of Annual Giving, Executive , Boston, Massachusetts