Director of Major and Planned Giving

THE OPPORTUNITY

Kents Hill is on a remarkable trajectory. Under the leadership of Head of School Dr. Molly MacKean, 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.

IN THIS ROLE, YOU WILL

BUILD AND LEAD THE MAJOR & PLANNED GIVING PROGRAM

● 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.

LEAD BY EXAMPLE AS A FRONTLINE FUNDRAISER

● 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.

BUILD AND COACH A HIGH-PERFORMING 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.

STRENGTHEN SYSTEMS, DATA, AND COLLABORATION

● 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, communications, and stewardship to ensure a coordinated, relationship-centered experience for donors and volunteers.

● Serve as a thought partner to the Chief Advancement Officer on budget planning, revenue forecasting, and campaign modeling for major and planned gifts.

WHO YOU ARE

You might see yourself in some of the following:

● You are an experienced major and planned giving fundraiser who has helped build or significantly grow a program and is ready to take the next step in leadership.

● You are a player-coach by nature—you’re comfortable doing the work yourself and equally energized by helping others learn to do it well.

● You’re excited, not deterred, by the idea of joining a nascent team where you will initially wear multiple hats, knowing that part of your impact will be building the structure and culture others will step into.

● You are a strategic relationship builder, able to see potential in people and partnerships and to connect that potential with institutional needs.

● You balance a bias for action (getting visits, making asks, improving a report) with big-picture thinking about how to build a sustainable, scalable major and planned giving program.

● You bring a learning mindset, humility, and a sense of humor to the work; you understand that building something new requires experimentation, reflection, and adjustment.

● You believe deeply in the transformative power of schools like Kents Hill and are excited to invite others into that story.

QUALIFICATIONS

● Bachelor’s degree

● 7–10+ years of progressive experience in advancement, with significant responsibility for major gifts and exposure to or leadership of planned giving programs.

● Demonstrated success in securing five-, six-, and seven-figure gifts from individuals and/or families; experience with capital or comprehensive campaigns is strongly preferred.

● Familiarity with gift planning vehicles (e.g., bequests, beneficiary designations, charitable trusts, gifts of securities and other non-cash assets) and comfort partnering with legal and financial advisors.

● Experience designing or improving prospect management systems, including portfolio design, moves management, metrics, and reporting.

● Prior experience supervising, coaching, or informally leading other fundraisers or advancement colleagues.

● Experience working in a growing or evolving advancement operation, with demonstrated comfort operating without a large existing team or fully built-out systems.

● A track record of both personal fundraising performance and contributing to or leading the design of new programs, initiatives, or teams.

● Excellent written and verbal communication skills, including the ability to craft clear cases for support and make confident, values-aligned asks.

● Superb verbal communication skills, public speaking experience, and the ability to represent Kents Hill effectively and professionally to potential donors and external organizations.

● Strong data literacy and comfort working in a CRM (Raiser’s Edge experience a plus) and with standard productivity tools.

● Willingness and ability to regularly travel domestically, and internationally as needed, and to work some evenings and weekends as donor and school events require.

WORK LOCATION

The ideal candidate will have an office at Kents Hill School and regularly work from campus. Considerations for remote work will be considered on a case-by-case basis.

COMPENSATION AND BENEFITS

This is a 12-month, exempt role that reports to the Chief Advancement Officer. Kents Hill School offers a competitive salary commensurate with experience and qualifications, and a comprehensive benefits package.

TO APPLY

Please send a cover letter and resume to hr@kentshill.org with the subject line “Director of Major and Planned Giving.”

Kents Hill School is an Equal Opportunity Employer committed to maintaining a work and learning environment free from discrimination on the basis of race, color, religion, national origin, pregnancy, gender identity, sexual orientation, marital/civil union status, ancestry, place of birth, age, citizenship status, veteran status, political affiliation, genetic information or disability, as defined and required by state and federal laws. Additionally, we prohibit retaliation against individuals who oppose such discrimination and harassment or who participate in an equal opportunity investigation.

Job Type: Full-time

Benefits:

  • 403(b) matching
  • Dental insurance
  • Health insurance
  • Health savings account
  • Life insurance
  • Paid time off
  • Retirement plan
  • Vision insurance

Work Location: In person

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