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Director of Gift Planning

Hotchkiss Brand
Lakeville, CT Full Time
POSTED ON 4/5/2026
AVAILABLE BEFORE 6/4/2026

Department:    Alumni Development

FLSA:                   Exempt

Reports to:       Executive Director of Leadership Giving

Status:              Staff, calendar year

Travel:              Regular

 

POSITION SUMMARY:

Over the last five years, Hotchkiss has built a modern, celebratory gift planning program. This best-in-class gift planning program has greatly expanded the membership in Hotchkiss’s legacy giving society, The Town Hill Society, welcoming members from a broad spectrum of class years, the youngest from the Class of 2014. To date, planned gifts have accounted for 15% of the total raised during Hotchkiss's Ever Forward campaign. Planned giving will continue to be an essential focus of Hotchkiss’s fundraising, and there is great opportunity to continue to expand awareness and close transformative planned gifts.

The Director of Gift Planning will be a seasoned gift officer who will bring intelligence, humor, ambition, warmth, and a persuasive understanding of planned giving to the role. Reporting to the Executive Director of Leadership Giving, the Director of Gift Planning will be a player/coach and will oversee a portfolio of current and prospective donors. Immersing themselves in ongoing education, the Director of Gift Planning will serve as the in-house expert on gift planning vehicles and the many benefits of deferred gifts, and lead a comprehensive marketing and gift planning outreach program. The Director will be a relationally motivated fundraiser, a creative thinker and problem solver, and an imaginative program builder.

Finally, the Director of Gift Planning will be an outstanding colleague working closely with development colleagues, trustees, faculty, administrators, and volunteers to identify prospective donors, cultivate relationships, solicit gifts, and provide thoughtful cultivation and stewardship in support of the School’s highest goals and priorities.

DUTIES AND RESPONSIBILITIES:

  • Steward and develop Hotchkiss’ robust, proactive gift planning program to meet the philanthropic objectives of Hotchkiss’ donors and the School’s fundraising goals;
  • Maintain personal philanthropic relationships with planned and major gift donors and manage a portfolio of 50-75 donors and donor prospects;
  • Creatively build the School’s planned giving stewardship program;
  • Oversee and initiate a multi-channel marketing and communications plan to increase significantly Town Hill Society membership and more closely and enthusiastically engage current membership;
  • Manage relationships with current and future gift planning vendors to leverage marketing and analytical tools;
  • Educate and coach development office colleagues and school colleagues about planned giving concepts, including bequests, retirement planning, life insurance, income tax planning, gifts of complex assets, life income gifts, and charitable trusts, and how these concepts can maximize philanthropy;
  • Promote gift planning with colleagues, donors, and trustees that will lead to new life income and estate gifts;
  • Provide support throughout complex gift conversations/solicitations, including donor visits with colleagues as needed and the writing of planned gift proposals;
  • Provide colleagues with written materials, illustrations, etc. to support their gift conversations;
  • Oversee one other gift officer focused on gift planning fundraising and program administration;
  • Use gift planning software and related services to provide gift illustrations for donors and donor prospects;
  • Provide staff and key volunteers with updates on legislative and/or legal issues that will impact charitable giving;
  • Report to departmental leadership and the Board of Trustees on the state and progress of gift planning at Hotchkiss.

SKILLS AND EXPERIENCE REQUIRED:

  • Bachelor’s degree required.
  • Seven to ten years of previous fundraising experience, preferably in secondary or higher education.
  • Experience developing and implementing donor-centric programs, communications, and events.
  • Experience working with wealthy, philanthropic individuals and their advisors.
  • Experience with charitable giving mechanisms and estate planning vehicles.
  • Exceptional interpersonal, organizational, and communications skills, including prospect management, written and oral presentation, and volunteer and staff coordination.
  • Self-motivated and possessing a demonstrated ability to articulate planned giving concepts and strategies with credibility to a diverse constituency.
  • Must be able to travel regularly and work flexible hours, when needed, including weekends and evenings.
  • Proficiency in G-Suite, PG Calc, Raiser’s Edge/NXT or similar fundraising software, and Microsoft Office.

PHYSICAL CONDITIONS:

  • Office environment.
  • At events, a significant amount of time standing/walking.
  • Repetitive (keyboard) motion.
  • Regular travel to meet with donors, attend events.

ADDITIONAL INFORMATION:

The essential functions and basic skills have been included in this description. It is not intended to be construed as an exhaustive list of all functions, responsibilities, skills and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.

 The Hotchkiss School is an equal opportunity employer and is committed to basing judgments concerning the employment of individuals upon their qualifications and abilities. The School is firmly committed to equal employment and advancement opportunities for all employees and applicants in all phases of the employment process (including recruitment, hiring, assignment, terms and conditions of employment, compensation, benefits, training, promotion, transfer, discipline and termination).

 In accordance with applicable law, the School does not discriminate against any individual based on age, ancestry, color, genetic information, learning disability, marital status, past or present history of mental disability, national origin, physical disability, race, religious creed, sex, pregnancy, sexual orientation, gender identity or expression, veteran status, or any other protected characteristic.

 

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