Director of Charitable Giving

The Position

Reporting to the Assistant Head of School for Advancement, the Director of Charitable Estate Giving is responsible for designing, implementing, managing, and coordinating a comprehensive estate giving program that supports the School's operating budget and endowment. The charitable estate giving program will be a combination of external donor visits and marketing (digital and direct mail) that reaches the Hill constituency far and wide. The Director partners heavily with the Major Gifts team.

The charitable estate giving program comprises gifts from alumni, parents, and other constituents. The Director leads estate giving strategy and program for all donors. The Director will also re-invigorate and assess The Matthew Meigs Society, the School's leadership giving society for donors who have included The Hill in their estate plans. The Meigs Society is The Hill's signature estate giving society with resonance and recognition within the Hill community. But it needs assessment and rebooting.

The Director must bring a "major gifts" approach to charitable estate giving, realizing that estate gifts result most from personal outreach and deep, meaningful relationships. Explaining the impact of estate gifts, and how they will be invested in its endowment and spent at the School is an essential skill for the Director. The successful candidate is a lead internal Director within the Advancement Office and a major gift officer for endowment and The Meigs Society. The Director is expected to make significant estate giving asks and travel nationally from July 1 through June 30 annually.

Estate giving marketing design and messaging are managed through a close partnership of the Director and Hill's Communications Office. The Director works closely with relevant Communications staff, executing appeals annually.

The Director works closely with all Advancement staff and interacts with other prominent and important Hill School leaders, trustees, and faculty as well as current students, occasionally.

The Hill is planning a new comprehensive campaign, launching in early 2027. The Director plays a key and substantial role in this campaign and is a consequential voice in its goals, objectives, and strategies.
Specific Responsibilities
Endowment Growth & Campaign Leadership

• Leverage and expand an immediate, qualified pool of 200+ established planned giving prospects to drive immediate growth for the School's permanent endowment.
• Integrate planned and deferred giving strategies directly into the priorities of our ambitious $200 million comprehensive campaign.
• Partner with advancement leadership and campaign committees to structure complex, multi-faceted gifts that combine current-use, capital, and endowment support.

Prospect Management & Donor Travel

• Manage a personalized portfolio of alumni, conducting an average of 10 to 12 face-to-face visits per month through regular domestic travel across the United States to secure deferred gifts (bequests, charitable remainder trusts, lead trusts, and gift annuities).
• Guide donors and their professional advisors (estate planning attorneys, CPAs, and wealth managers) through custom gift planning options that align with their personal philanthropic and financial goals.
• Collaborate seamlessly with major gift officers to identify secondary planned giving opportunities within existing portfolios.

Stewardship & Program Operations

• Direct the strategy and expansion of our Matthew Meigs Society, curating exclusive engagement opportunities, communications, and campus events to honor our estate giving donors.
• Partner with the communications team to produce targeted marketing materials, impact stories, and estate planning educational resources tailored to a boarding school community.
• Maintain precise records of prospect cultivation stages, gift documentation, and trust tracking within our CRM database.
• Maintain PG Calc and annuity state registrations annually; maintain Hill's charitable estate giving website.

The Candidate

The ideal candidate will hit the ground running with an existing, highly warm donor pool of over 200 prospects who have already indicated they have included Hill in their estate plans or are actively willing to discuss legacy commitments. Furthermore, the Director will play an instrumental role in our burgeoning $200 million comprehensive campaign, gaining invaluable, high-profile fundraising experience in a premier independent school environment. This position offers a work schedule complemented by domestic travel across the United States to cultivate and steward meaningful donor relationships.
Qualifications

• A deep appreciation for independent boarding school traditions, residential life, and the unique culture of a close-knit educational community.
• Minimum of 3 to 5 years of progressive experience in Advancement and charitable estate giving, law (trusts and estates), or wealth management.
• Comprehensive understanding of charitable tax laws, IRS regulations, estate planning vehicles, and endowment management principles preferred.
• Excellent organizational, interpersonal, verbal/written communication skills.
• Excellent social skills, with large groups as well as with individuals.
• Able to work independently and part of a team.
• Detail-oriented, well organized, focused, and goal-oriented, with a high level of initiative and energy, as well as adept at problem solving and using judgment in situations requiring independent initiative and tact.
• Exceptional emotional intelligence, absolute discretion with confidential matters, and the ability to translate complex financial and legal concepts into compelling philanthropic visions for donors.
• Bachelor's degree required; Juris Doctor (J.D.) or advanced legal/tax training is strongly preferred.
• Must be willing and able to travel domestically to meet donor expectations.

Attitude and Demeanor

• Publicly support the mission and vision of The Hill School in a positive and professional manner.
• Work as a dynamic team member in a professional collaborative environment.
• Energetic and organized enough to thrive in an extremely fast-paced environment while collaborating with a growing team to produce great work.
• Ability to wear many hats, learn new things every day, and have the ability to switch from a variety of roles with ease and excitement.
• Communicate effectively with warmth, sensitivity, humor, and understanding as they deal with administrative colleagues, teachers, students, alumni, parents, faculty, staff, and program associates.
• Possess a "service attitude" - willingness to be flexible to meet the needs of the department and school.

The Hill School offers a competitive salary, an excellent benefits package, and a generous retirement plan.