Director of Annual Giving

The Winsor School; Boston (MA); On-site; USD 120,000 - 165,000; Full time

Job summary

The Winsor School in Boston, MA seeks a strategic Director of Annual Giving to lead the Winsor Fund's planning and multi‑channel campaigns. You will direct the annual giving program, oversee the team, and set donor engagement strategies to meet revenue and participation goals.

Reporting to the Chief Advancement Officer, you will collaborate across Advancement and Communications, manage volunteers and staff, and drive data‑driven fundraising with a focus on stewardship and donor retention.

Qualifications

• A Bachelor’s degree.
• At least five years of development/fundraising experience; annual giving and frontline fundraising preferred.
• Demonstrated success managing professional staff and volunteers.

Responsibilities

• Plan and lead annual giving program and team.
• Establish metrics for donor retention, acquisition, and leadership upgrades.
• Collaborate with CAO and board committees on reports and strategy.
• Hire, coach, and motivate annual giving staff.
• Oversee data analytics, gift processing, and reporting workflows.
• Coordinate with volunteers and events to strengthen stewardship.

Education

Bachelor’s degree

Job description

Posted: Aug 9, 2026

Director of Annual Giving

The Winsor School - Boston, MA

business_center Full-time

Salary: $120,000.00 - $165,000.00 Annually

Application Deadline: 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.

Essential Functions

Annual Fund Program and Team Management (35%)

• 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.

Direct Marketing (10%)

• Drive the development of a communications plan, including timeline, work with mailhouses, 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.

Portfolio and Prospect Management (15%)

• 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.

Volunteer Management (30%)

• 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, and manage volunteer committees or cohorts to scale peer‑to‑peer fundraising efforts.
• Serve as liaison with GiveCampus for crowdfunding and volunteer platforms.
• Create meaningful and educational materials (talking points, templates, etc.) to aid volunteers in successful relationship‑building and peer solicitations.
• Provide high‑level volunteer support to the President of the Winsor Board of Trustees, Annual Giving 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.

Other Responsibilities (10%)

• Work with the Operations team to ensure timely gift processing and reporting and 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.
• Provide exceptional collaboration strategy and customer service to all key stakeholders.
• Perform other duties as assigned by the head of school or supervisor.
• Attend mandatory meetings, including, but not limited to, opening and closing meetings, faculty/staff meetings, division meetings, and department meetings.

Required Qualifications

• A Bachelor’s degree.
• At least five years of development/fundraising experience; experience with annual giving and frontline fundraising preferred.
• Demonstrated success managing professional staff and volunteers.

Preferred Qualifications And Skills

• Talent for developing meaningful, genuine relationships.
• Proven track record of soliciting and closing lead annual fund gifts.
• Strong public speaking, presentation, and communication skills.
• A thorough knowledge of Word, Excel, PowerPoint, and preferably Raiser’s Edge or equivalent CRM database.
• Excellent attention to detail as well as organizational, analytical, time management, and problem‑solving skills.
• Ability to manage multiple projects successfully in a fast‑paced environment.
• Ability to work independently and as a member of a team.
• Proven ability to manage diverse teams, supporting both front‑line fundraising/communications staff and technical database/operations staff. Strong commitment to professional development and coaching for team members.
• 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.

Work Environment and Physical Demands

• Frequent talking, listening, walking, sitting and standing.
• Ability to perform multiple concurrent tasks and function in a fast‑paced working environment.
• Occasional evening and weekend work is required to support key advancement events, committee meetings, and donor engagement opportunities.

The salary range is $120,000–$165,000.

Nothing in this Job Description restricts Winsor’s right to assign or reassign duties and responsibilities to this position at any time.