Leadership Gift Officer

New Milford, Connecticut, Position: Leadership Gift Officer

Reports to: Chief Advancement Officer

Position Summary: The Advancement Office is responsible for cultivating and expanding philanthropic support among alumni, parents, past parents and friends of Canterbury School. The Leadership Gift Officer is responsible for identifying, qualifying, cultivating, soliciting, and stewarding a portfolio of leadership-level ($1,915+) donors and reunion prospects.

The ideal candidate is a strategic relationship builder with the confidence to inspire meaningful philanthropic investment through personalized, in-person engagement. This position requires regular travel approximately 30-40% of the time, and includes some evening and weekend responsibilities.

Essential Responsibilities:

Manage a portfolio of 125-150 leadership-level donors and prospective donors, with an emphasis on acquiring new donors, reactivating lapsed donors, and upgrading existing donors. Build and strengthen relationships through personalized outreach, including face-to-face visits, phone calls, zooms, and meaningful donor encounters. Devise individual engagement strategies for each prospect, with the goal of soliciting annual gifts ($1,915+) and multi-year pledges ($10k+). Monitor progress toward fundraising goals, providing regular updates to internal stakeholders and volunteers. Collaborate with Advancement colleagues and campus partners to ensure consistent strategy, messaging, and donor experience. Meet or exceed individual fundraising goals while contributing to broader advancement and reunion fundraising objectives.

Skills and Abilities:

Authentic desire to work in an independent school environment, and willingness to travel extensively to strengthen relationships with donors and prospective donors. Adhere to ethical fundraising practice, including transparency, confidentiality, and respect for donor intent, while upholding the highest standards of integrity and professionalism. Highly organized, proactive and self-motivated, with a willingness to initiate outreach and pursue new opportunities. Excellent interpersonal, communication and listening skills, with the ability to build rapport quickly and effectively. Independent secondary school or higher education experience preferred. Bachelor’s degree and a minimum of two years of fundraising experience required.

Bachelor’s Degree Minimum of two years of fundraising experience