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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, GiveCampus 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 GiveCampus and related annual giving tools to support The Westminster Fund, digital giving, volunteer outreach and campaign reporting.
• Ensure the Assistant Director of Annual Giving is equipped to serve as the lead staff user for the GiveCampus Volunteer Management System.
• Use GiveCampus, Raiser’s Edge NXT and related tools to evaluate donor behavior, volunteer activity, peer-to-peer outreach and annual giving results.
• Partner with Advancement Services to ensure data, appeal codes, volunteer assignments, gift activity and campaign results are accurate and reconciled appropriately.
• Manage annual giving solicitation strategy across direct mail, email, digital giving, volunteer outreach, events and personal follow-up.
• Manage a portfolio of 50-60 leadership Annual Giving prospects, conduct donor visits, and personally solicit and close gifts.
• Identify donors with upgrade potential, leadership annual giving capacity or readiness for deeper engagement.
• Partner with Major Gifts, Gift Planning, Alumni Engagement and Parent Engagement to ensure strong handoffs and coordinated donor strategy.
• Partner with Advancement Communications to develop clear, donor-centered Westminster Fund messaging across print, digital, volunteer and event-based channels.
• Partner with Stewardship to create timely and meaningful donor recognition, impact reporting and follow-up for Westminster Fund donors.
• Work closely with the Director of Advancement Operations to ensure annual giving strategy is aligned with Advancement Office systems, reporting, data health, campaign calendars, stewardship coordination and cross-office planning.

Job Qualifications

• Bachelor’s degree in related field required.
• Five to seven years of experience in annual giving, advancement, independent school fundraising, higher education advancement, nonprofit fundraising, volunteer management, or related work preferred.
• Demonstrated ability to develop and execute annual giving strategies that increase dollars, participation, retention, and donor engagement.
• Experience managing staff, volunteers, campaigns, communications calendars, and multi-channel solicitations.
• Strong understanding of annual giving best practices, donor segmentation, volunteer engagement, digital fundraising, and campaign analysis.
• Experience with GiveCampus, the GiveCampus Volunteer Management System, Raiser’s Edge NXT, or similar fundraising platforms preferred.
• Strong written and verbal communication skills.
• Ability to translate fundraising priorities into clear, donor-centered language.
• Strong organizational and project management skills.
• Comfort using data to guide outreach, measure performance, and improve results.
• Ability to build relationships with donors, volunteers, alumni, parents, and colleagues.
• High attention to detail, discretion, judgment, and follow-through.
• Ability to travel and work occasional evenings and weekends for events, volunteer meetings, and campaign activity.

Westminster School is an Affirmative Action Equal Opportunity Employer and encourages applications from candidates of color. Westminster School reaffirms its long-standing nondiscriminatory policy and employs individuals of any race, religion, sexual orientation, gender identity, or national origin to all the rights, privileges, programs, and activities generally accorded or made available at Westminster. Westminster does not discriminate in its hiring, educational policies, admissions policies, scholarship programs, or athletic and other school-administered programs.

995 Hopmeadow Street
Simsbury, Connecticut 06070

P. (860) 408-3000
F. (860) 408 3001

Notice of Nondiscriminatory Policy as to Students
In keeping with our support for a diverse community, Westminster abides by all applicable federal and state laws and does not discriminate on the basis of any protected characteristic, including race, color, religious creed, sex, sexual orientation, gender identity or expression, national and ethnic origin, ancestry and/or disability in administration of its educational policies, admissions policies, scholarship and loan programs, and athletic and other school-administered programs. Westminster admits students of any race, color, national and ethnic origin to all the rights, the privileges, programs, and activities generally accorded or made available to students at the School.