Director of Major and Planned Giving

Job Description THE OPPORTUNITY

Kents Hill is on a remarkable trajectory. Under the leadership of Head of School Dr. Molly Mac Kean, the school is embracing a 200-year-old legacy and accelerating a bold and exciting vision for the future. Kents Hill is reshaping not only what it teaches but how, where, and when. The school is reimagining spaces to bring creativity, innovation, and collaboration to life, as well as rethinking how the school can use time throughout the entire calendar year to foster growth.

Kents Hill is leaning into this moment with imagination and resolve. A forthcoming comprehensive campaign—significantly larger than any in the school’s history—will fuel this vision and expand access, programs, and facilities for generations to come. The Director of Major and Planned Giving will be a central partner in making that possible.

As Director of Major and Planned Giving at Kents Hill School, you will initially serve as a hands‑on frontline fundraiser while also laying the groundwork for a major and planned giving program and team that can scale. Partnering closely with Chief Advancement Officer Erin Fogg, you will help prepare the school for an unprecedented comprehensive campaign—designing strategy, building systems, personally leading key donor relationships, and, over time, hiring and mentoring additional team members.

In the early years, this role will be heavily focused on direct portfolio work and building core infrastructure. As the program matures, it will evolve into a player‑coach leadership role, with increasing responsibility for managing and developing a team of gift officers and gift planning staff.

This role is ideal for someone who is excited by both vision and execution: someone who is as comfortable sketching out a campaign roadmap as making the solicitation, cleaning up a moves‑management report, or modeling good practice on a donor visit.

This role reports to the Chief Advancement Officer and plays a key leadership role within a growing Advancement team that values adaptability, creativity, courage, and disciplined follow‑through.

• Design and implement a comprehensive major and planned giving strategy that aligns with Kents Hill’s strategic vision and campaign priorities.
• Develop and own the planned giving strategy, including implementing marketing and prospect identification.
• Partner closely with the Chief Advancement Officer to shape campaign strategy.
• Phase the work thoughtfully, recognizing that in the near term you will personally handle much of the portfolio work and infrastructure‑building, and in the longer term you will shift more time toward leading and strategizing.

• Manage a portfolio of high‑capacity prospects and donors.
• Guide donors through the full cycle of identification, cultivation, solicitation, and stewardship.
• Make bold, thoughtful asks for current‑use, capital, and endowment priorities, as well as planned gifts, with clarity, courage, and care.
• Develop personalized, compelling written proposals, and impact reports that connect donor interests with Kents Hill’s strategic needs.
• Model best practices in portfolio management, outreach, and stewardship that can later be adopted and scaled by a growing team.

• Help define the future staffing structure for major and planned giving.
• In the early years, serve as a player‑coach without a large direct‑report structure, modeling best practices and collaborating closely with colleagues across Advancement.
• As the team grows, help define roles, recruit and onboard new staff, and formalize management responsibilities, including goal‑setting, feedback, and professional development.
• Foster a team culture that values adaptability, creativity, courage, and disciplined follow‑through—and that takes joy and pride in building good habits and practices together.

• Partner with Advancement Operations to optimize the CRM (Raiser’s Edge NXT) and related tools.
• Work closely with colleagues in annual giving, alumni and parent engagement,…