Director of Annual Giving

Westminster School, one of the leading independent boarding schools in the country, is a diverse, close-knit community of approximately 190 employees and 430 students (seventy-five percent boarding, twenty-five percent day students) set on a 200-acre campus in Simsbury, Connecticut. Since its founding in 1888, Westminster School has been committed to the core values of community, character, balance, and involvement. Our motto describes our community – “virtute et numine” – by Grit & Grace.

From a philanthropic perspective, Westminster is operating from a position of strength. The school completed a $102 million comprehensive campaign in 2021 and continues to build on that momentum. Today, fundraising centers on The Westminster Fund, which raises more than $3.2 million annually, as well as capital, endowed and donor-directed support for Westminster’s people, programs and strategic priorities. Together, these efforts generate more than $10 million in philanthropic support each year.

Position Summary

Westminster School seeks a strategic, organized and results-oriented Director of Annual Giving to serve as a senior member of the Advancement team. This individual will lead The Westminster Fund and strengthen annual philanthropic support across Trustees, alumni, parents, grandparents, faculty, staff and friends. Reporting to the Director of Advancement Operations, the Director of Annual Giving is responsible for revenue generation, annual giving strategy, campaign execution, donor segmentation, volunteer structure, systems use and cross-office coordination.

The Director will manage The Westminster Fund, which raises more than $3.2 million annually, and will lead efforts to grow dollars, participation, donor retention, leadership annual giving, and broad community engagement. This role oversees annual giving strategy for 1888 Minutes of Giving, calendar-year-end outreach, fiscal-year-end giving, reunion giving, alumni participation and parent giving in close partnership with colleagues across Advancement. This role also creates strategy and provides oversight for the Reunion Giving Program.

The Director of Annual Giving will supervise the Assistant Director of Annual Giving, who manages day-to-day class agent engagement, reunion committee management, Give Campus Volunteer Management System activity and volunteer communications. Together, these roles ensure a consistent, strategic and measurable volunteer program of nearly 400 engaged alumni that supports The Westminster Fund, reunion giving, 1888 Minutes of Giving and alumni participation overall.

The successful candidate will be a disciplined fundraiser, strong manager, clear communicator and collaborative colleague who can balance strategy and execution, use data to guide decisions, manage staff and volunteers effectively and keep The Westminster Fund visible as a central philanthropic priority for Westminster.

Primary Duties and Responsibilities

• Lead strategy and execution for The Westminster Fund, including annual goals, donor segmentation, solicitation calendar, messaging, stewardship coordination, reporting and performance analysis.
• Develop and manage a Table of Gifts that includes ask amounts, prospect assignments and strategies for leadership annual giving prospects.
• Set and monitor annual giving goals by constituency, including alumni, parents, grandparents, faculty, staff and friends.
• Build targeted strategies for key donor segments, including LYBUNTs, SYBUNTs, lapsed donors, leadership annual giving prospects, reunion classes, young alumni, current parents and loyal donors.
• Supervise, support and guide the Assistant Director of Annual Giving.
• Provide strategic oversight for class agent and reunion committee volunteer programs.
• Partner with the Assistant Director of Annual Giving to develop clear roles, expectations, training, timelines and goals for class agents and reunion committee members.
• Lead overall strategy and execution for 1888 Minutes of Giving, Westminster’s annual giving days.
• Coordinate campaign goals, challenge gifts, leadership outreach, segmented messaging, volunteer mobilization and follow-up.
• Oversee strategic use of Give Campus and…