A premier independent boarding school nestled in Connecticut’s northwest corner, The Hotchkiss School has cultivated excellence in scholarship, character, and community for over 130 years. Each year, Hotchkiss welcomes more than 600 students from across the globe, preparing them for lives of meaning and impact through a rigorous academic program and a transformative residential experience.

The Opportunity

As the School progresses through the public phase of the historic $250 million Ever Forward campaign—its first in nearly 30 years—Hotchkiss seeks a strategic, growth-oriented Executive Director of The Hotchkiss Fund to lead and expand a $7 million-plus annual giving program that is essential to the School’s continued momentum.

Reporting to the Chief Advancement Officer and serving as a senior member of the 27-person Alumni and Development team, the Executive Director will be a vital partner in sustaining and growing a best-in-class annual giving program. This leader will guide a team of professional staff, collaborate with colleagues across all advancement functions, and engage a dedicated volunteer network to elevate participation, grow the donor pipeline, and increase philanthropic impact.

The Executive Director will be both a strategist and a storyteller—someone with data fluency, marketing acumen, and the ability to inspire support through compelling messages and authentic relationships.

The ideal candidate will bring proven experience managing annual giving programs in a campaign environment, with a deep understanding of segmentation, stewardship, and volunteer engagement.

This is a unique opportunity to build on years of record-breaking annual fund success and shape the next chapter of donor engagement for one of the nation’s most respected independent schools.