Director of Annual Giving

Salary: $ - $ Annually

Final date to receive applications:
Oct 15, 2026

Education

Job Description:

Director of Annual Giving
Position:
Director of Annual Giving

Reports to:

Chief Advancement Officer
Department:
Advancement
Classification:
Exempt, 12-month

Position Summary
The Director of Annual Giving leads the strategic planning and execution of the Winsor Fund to meet revenue and participation goals. Through a multi-channel annual campaign — including direct marketing, volunteer recruitment and management, and direct solicitation — the Director drives annual giving success. This role oversees all aspects of the annual giving program as well as the annual giving team, managing the Associate Director of Advancement Operations and the Assistant Director of Annual Giving.

There is also opportunity to elevate reunion giving and weave annual giving messaging into the entirety of the school programming and events.

This is a 12-month position reporting to the Chief Advancement Officer.

• Plan and execute strategies to set and achieve ambitious annual giving goals.
• Establish, track, and meet specific metrics for donor retention, acquisition, leadership-level upgrades, and dollars raised. Create and track against Winsor Fund gift pyramid.
• Collaborate with colleagues to integrate annual giving, reunion giving, and major gift solicitation strategies.
• Serve as a resource for fundraising staff and volunteers.
• In collaboration with the CAO, prepare reports and presentations for the Board of Trustees, Advancement Committee, Finance Committee, Campaign co-chairs, and other key stakeholders.
• Hire, onboard, lead, coach, and motivate annual giving team, including the Assistant Director of Annual Giving and the Associate Director of Advancement Operations (who is responsible for the gift processing, database, and reporting needs of the office).
• Track and lead the annual giving budget.
• In partnership with the Associate Director of Advancement Operations, leverage data analytics, predictive modeling, and donor database segmentations to identify giving trends, evaluate appeal ROI, and drive data-informed fundraising strategies.
• Collaborate on the creation and execution of a comprehensive stewardship and loyalty program (e.g., consecutive years giving societies) to recognize and retain Winsor Fund donors.

• Drive the development of a communications plan, including timeline, work with mail houses, appeal signers, etc., 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 Associate Director’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.
• Oversee the direct marketing strategy behind Giving Day; keep up on modern giving technologies to implement where appropriate.

• Manage a small portfolio of lead annual giving prospects, actively identifying, cultivating, soliciting, and stewarding donors to secure leadership-level annual gifts.
• Establish strategic cultivation and solicitation plans for individual prospects within the portfolio, coordinating with major gift officers to align prospect pipelines.
• Prepare timely, constructive, and complete contact reports, proposals, and deliverables for internal stakeholders; deliver timely and effective follow-up to prospects and donors.
• Personally thank donors within the pool for their Winsor Fund gifts. Work collaboratively to maintain a strong stewardship strategy for portfolio donors to encourage donor retention.
• In consultation with the CAO, set a target for number of solicitations per year and a dollar goal for the pool overall.

• In collaboration with the CAO, lead the Annual Giving Committee and other high-level volunteers; strategize and prepare for Committee meetings.
• Lead volunteer recruitment and engagement strategy for annual giving alumnae and parent volunteers; recruit, train,…