Head of School Search
Head of School Search
The search for Upland’s next Head of School is national in scope and is expected to attract a strong pool of talented candidates. We are committed to an inclusive and transparent process while respecting the confidentiality of all applicants.
Head of School searches are dynamic, and timelines may shift as the process unfolds. While specific dates may change, our commitment to appointing an exceptional leader for Upland remains constant.
Community members are encouraged to share questions, input, or candidate recommendations with the Search Committee at [email protected].
On behalf of the Board of Trustees and the Search Committee, thank you for your continued support of Upland Country Day School.
Very truly yours,
Charlie Gerbron ’95, P’29, ’32, ’36
Chair, Head of School Search Committee
Trustee, Upland Country Day School
Position Description
Upland seeks a dynamic and visionary Head of School for a July 2026 appointment. The ideal candidate will hold at least a bachelor’s degree (advanced degree preferred) and bring senior leadership experience in an independent school setting, ideally at the elementary and/or middle school level. This leader will demonstrate strength in faculty and team management, curriculum design and implementation, relationship building and fundraising, strategic planning and Board partnership, and budget development and oversight.
Upland is looking for an empathic, confident, and decisive leader who is a visible and positive presence in the community. The successful candidate will be a seasoned educator with a passion for teaching and learning, a thoughtful strategic thinker, and an effective communicator capable of inspiring others. Above all, this individual will be a compassionate and inclusive community builder and a wise steward of Upland’s culture and mission.
To learn more about this opportunity, please click below.
Posted Communications
"To visit Upland is to see a school whose time is now. Founded in 1948, Upland is a thriving PK–9 community defined by discovery, challenge, inclusion, creativity, and joy—set on a beautiful campus, led by dedicated educators, and guided by a committed Board of Trustees."
Explore Our Academic Programming
We believe children rise to our highest expectations, thrive on meaningful challenges, and never deserve anything less. Explore the multidimensional growth experience specifically designed to prepare each student for the future in each of our core schools:
Y9 Experience
(9th Grade)
Developing as role models and leaders for an entire student body.