Demo

Associate Director, Principal Gifts

Hotchkiss Brand
Lakeville, CT Full Time
POSTED ON 8/28/2026
AVAILABLE BEFORE 10/28/2026

Department:   Alumni and Development

FLSA:                 Exempt

Designation:   Full-time Calendar Year (some weekend and evening work required)

Reports to:      Senior Advisor, Principal Gifts

Location:         On-Campus / In-Person (Lakeville, CT)

Travel:              Off-campus events and donor meetings

 

SUMMARY:
The Associate Director, Principal Gifts, is an integral part of the Principal Gifts and Leadership Giving teams, cultivating mutually beneficial relationships with alumni and parents to secure leadership and ultimately transformational support for The Hotchkiss School. Reporting to the Senior Advisor, Principal Gifts, the Associate Director is engaged in all activities in the comprehensive engagement, cultivation, solicitation, and stewardship of principal gift-level donors and prospects, defined as prospects capable of making gifts of $1M or more over five years. The Associate Director, Principal Gifts, works cooperatively with a wide variety of colleagues, including School leadership, faculty, staff, and volunteers, to help execute donor engagement and stewardship strategies.

The Associate Director is a strategic partner to frontline fundraisers, cultivating and soliciting prospects by designing and implementing highly personalized donor engagement, cultivation, and stewardship experiences, while also supporting the strategic vision of the principal gifts program. The position delivers exceptional service to our donors and plays a central role in setting and delivering principal gifts fundraising and engagement strategies, and meeting program goals.

This is a full-time, on-campus role for someone who thrives on direct, personal interaction. Working closely with the Head of School and gift officers, the Associate Director acts as the on-the-ground resource for major donors, parents, and alumni.

This position handles highly confidential information daily and uses discretion when sharing it with internal and external stakeholders.

ESSENTIAL FUNCTIONS:

Principal Gift Strategy and Relationship Management 50%

  • Responsible for supporting and helping to develop personalized cultivations and solicitations of principal gifts, aligned with the overall donor strategy. This includes helping to implement gift plans with all gift officers assigned to principal gift prospects and donors.
  • Develops tailored stewardship plans for principal gift donors that illuminate the impact of their gifts and ensure a high-quality donor experience.
  • Meets with the Senior Advisor, Principal gifts and other internal stakeholders as needed to discuss and strategize cultivation and stewardship opportunities for the entire pool of principal gift prospects.
  • Supports the strategic engagement plan for identified principal gift prospects. Writes and submits contact reports and compiles other pertinent information following donor contacts.
  • Provides high-level, personalized support for the identification, cultivation, solicitation and stewardship of Hotchkiss alumni and parents.
  • Drafts, edits, and tracks pledge agreements, gift agreements, and endowment terms.
  • Monitors the movement of donors through the gift pipeline, ensuring cultivation and stewardship strategies set by leadership are implemented.
  • Collaborates with Research to identify high-net-worth individuals and prepare background dossiers for upcoming meetings.
  • Travels as needed to support the principal gift program at various events and engagement opportunities.

Writing 30%

  • Creates and provides input on gift proposals to support donor solicitation and yield gifts toward institutional priorities.
  • Reviews and finalizes briefing documents for leadership that articulate donor strategy to ensure goals for prospect development are clearly defined, and leadership is prepared for donor conversations.
  • Researches, writes, and edits collateral, various donor communications, and endowment reports for principal gift donors, coordinating with colleagues, faculty, and leadership to create personal and accurate communications.

Project Management 20%

  • In conjunction with key stakeholders, helps design, create, and proactively track cultivation, solicitation, and stewardship deliverables.
  • Collaborates with key personnel to source information needed for cultivation, solicitation, and stewardship requirements related to prospect management and donor gifts.
  • Coordinates and manages Principal Gift projects and events.

Perform other duties as assigned.

SKILLS AND EXPERIENCE REQUIRED:

  • Bachelor's or equivalent combination of education and experience.
  • 7–10 years of experience in fundraising; or equivalent professional experience in high-net-worth relationship management, wealth management, institutional insurance, or client relations.
  • Understanding of and appreciation for the philanthropic process and individual giving behaviors, combined with relationship management experience.
  • Preferred experience with Raiser’s Edge or similar CRM, as well as the suites of Office and Google products.
  • Writing and communications experience in higher education or a non-profit environment preferred.
  • Demonstrated writing experience, preferably in the creation of donor communications.
  • Exemplary written and verbal communication and negotiation skills
  • Strong customer service orientation and interpersonal skills.
  • Exceptional planning, administrative, and organizational skills, ability to take initiative, manage time efficiently, meet deadlines, and manage competing priorities.
  • Exceptional customer service skills. Demonstrated ability to work in a consistently positive and productive manner – including donors, alumni, and colleagues.
  • Flexibility and creativity.
  • Ability to work both independently and in a collaborative team environment.
  • Ability to handle sensitive and confidential matters with discretion and to manage. internal conflict in ways that lead to enhanced teamwork.
  • Brings joy and a sense of humor to work.

PHYSICAL CONDITIONS:

  • Office environment.
  • Repetitive (keyboard) motion.
  • At events, a significant amount of time standing/walking.
  • Periodic need to carry boxes (no more than 50 lbs), move tables and chairs, hang signs, and other similar tasks for events.

ADDITIONAL INFORMATION:

A cover letter and resume are required for consideration. In your cover letter, please highlight your relevant experience in major/principal gifts fundraising or transferable client relationship management.

The essential functions and basic skills have been included.  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.

 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.

 

Salary.com Estimation for Associate Director, Principal Gifts in Lakeville, CT
$130,080 to $191,646
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