Leadership Gifts Officer

Start Date:

September 1, 2026

Saxtons River, Vermont

Chief Advancement Officer

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.

• 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 efforts for leadership and major donors, including those supporting endowed or named funds.
• Partner with the Advancement team to create annual impact reports, campaign updates, stewardship materials, and personalized donor communications.
• Ensure donors experience consistent, meaningful recognition and engagement through events, reporting, outreach, and ongoing relationship management.
• Help foster a culture of gratitude, professionalism, and responsiveness throughout the Advancement Office.

• Participate actively in school life, including attendance at major events, performances, athletic competitions, assemblies, and community programming.
• Recognize that advancement work is most effective when grounded in authentic connection to the daily life of the school.
• Serve as a collaborative and mission-aligned partner across departments and constituent groups.
• Support additional Advancement initiatives and special projects as needed.

• A compelling relationship-builder who leads with warmth, authenticity, and professionalism.
• A strategic thinker who can balance long-term vision with disciplined execution.
• A highly organized…