Leadership Gifts Officer

Collaborates Closely With:

Head of School, Advancement Team, Trustees, Alumni, Parents, and Volunteers

Vermont Academy seeks a strategic, relational, and highly motivated Leadership Gifts Officer to help advance one of the most important moments in the school’s history. As Vermont Academy approaches its 150th anniversary and launches the Where Vision Meets Purpose Campaign in support of Vision 2030, this role will help shape the philanthropic future of the institution.

At Vermont Academy, advancement work is deeply relational. It is rooted in listening carefully, building authentic trust, and connecting donors to a compelling vision for young people and the future of the school. The Chief Advancement Officer will work closely with the Leadership Gifts Officer who will cultivate and steward meaningful partnerships with alumni, families, grandparents, and friends of Vermont Academy—helping supporters align their philanthropy with the mission, priorities, and long-term sustainability of the school.

This role combines frontline fundraising, strategic planning, donor stewardship, and an understanding of campaign management. The ideal candidate is equally comfortable building relationships over time, executing sophisticated fundraising strategies, and helping coordinate the systems and momentum necessary for a successful comprehensive campaign.

Working closely with the Chief Advancement Officer and Head of School, this individual will help drive leadership annual giving, work on bridging mid level donors into major donors, campaign planning, and endowment growth during a transformative chapter in Vermont Academy’s history.

This is a full-time, 12-month administrative position with significant travel (75%) and active engagement in school life.

• Manage and strategically advance a dynamic portfolio of approximately 100–125 major gift prospects and donors, including alumni, current parents, parents of alumni, grandparents, and friends of the school.
• Develop and implement individualized cultivation, solicitation, and stewardship strategies designed to deepen engagement and secure philanthropic support, primarily in the $10,000–$50,000 range, while also supporting select six-figure opportunities.
• Identify, qualify, and build the major gift pipeline through prospect research, referrals, relationship mapping, and ongoing engagement strategies.
• Conduct meaningful donor conversations that connect Vermont Academy’s mission, strategic priorities, and student experience to philanthropic investment opportunities.
• Arrange, prepare for, staff, and follow up on donor meetings involving the Head of School, Chief Advancement Officer, trustees, and other key school leaders.
• Develop a deep understanding of Vermont Academy’s academic programs, student life, strategic plan, and institutional priorities in order to articulate a compelling case for support.

• Partner closely with the Chief Advancement Officer on the planning and execution of the Where Vision Meets Purpose Campaign and other strategic fundraising initiatives.
• Support campaign planning efforts including prospect strategy, timelines, donor communications, cultivation events, volunteer coordination, and proposal development.
• Help coordinate leadership giving strategies tied to annual, capital, endowment, deferred, and non-cash gifts.
• Conduct and oversee prospect research for campaign and leadership-giving priorities, including research on newly enrolled families and emerging donor opportunities.
• Collaborate with the Director of Annual Giving and the Alumni Engagement Officer to ensure thoughtful donor movement and coordinated engagement across giving levels.
• Analyze giving trends and prepare reports, updates, and prospect strategy materials for senior leadership and Board committees.
• Maintain accurate and strategic documentation of donor engagement and solicitation activity within Advancement’s database, utilizing Blackbaud Raisers Edge and related systems.

• Lead thoughtful stewardship…