Director, Annual Giving & Donor Engagement

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

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.