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. The school completed a $102 million comprehensive campaign in 2021 and continues to build on that momentum, generating more than $10 million in philanthropic support each year through The Westminster Fund and other efforts.

About the role

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.

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, including 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.

Qualifications

• Bachelor’s degree in a 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, with the 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.

Benefits

• Outstanding health care coverage.
• Retirement plan.

Pay

Salary is competitive.