Head of School Search

Dear Aspen Country Day School Community,

When Josh recently shared with the Board of Trustees his decision to return to the East Coast, we felt a mix of emotions: sadness at saying goodbye to a cherished colleague and friend, gratitude for all he has accomplished, and genuine excitement for him and for Rachel as they move closer to their families.

With the support of a talented faculty and staff, an exceptional senior leadership team, and a deeply committed Board of Trustees, Josh has helped shape Aspen Country Day School into the remarkable PreK to Eighth Grade independent school it is today. We are fortunate to benefit from his steady leadership throughout this upcoming year of transition.

As a Board, we knew this moment would someday arrive. We are prepared for this transition, and we view it as an extraordinary opportunity for Aspen Country Day School to build upon our existing strong foundation, which includes:  

• A thoughtfully developed Strategic Plan, now entering its implementation phase, that will significantly enhance both our campus and our educational experience.
• A strengthened and more rigorous academic program, including an enhanced scope and sequence in the Lower School and a revitalized math curriculum in the Middle School.
• Outstanding high school placement outcomes in a highly competitive landscape, with our Aardvarks continuing to earn spots at their top-choice schools—whether boarding schools, Aspen High School, or other local institutions.
• A beautiful campus accompanied by 13 school-owned faculty residences.
• A solid financial position marked by balanced budgets and a healthy endowment.
• A generous financial aid program that will open our community to even more deserving students.

Aspen Country Day School is thriving, thanks to the dedication of Josh and his team, and we are confident that the opportunity to lead our school into its next chapter will attract exceptional candidates from across the country and within our own community.

With that in mind, we now begin the search process. The Board has passed a resolution to form a Head of School Search Committee that will represent every part of our community, including faculty, alumni, and Trustees. We will soon begin conversations with leading national search firms to identify the partner best suited to support this important work. These firms understand the remarkable progress of the past 12 years and the exciting opportunity this leadership role presents, and they are eager to assist us.

While we intend to move efficiently, we will also proceed with great care. Our commitment is to find the right leader—someone who will propel Aspen Country Day School forward while honoring the values and lessons that have guided us for 56 years. As part of this process, we will invite input from all corners of our community. Our search will be inclusive, transparent, and grounded in both our aspirations and our history.

As always, Josh, our faculty and staff, and the Board of Trustees will rely on your partnership and support as we begin this next chapter in the ACDS story. We will keep you informed at every step.

With gratitude,

Bret Hirsh P’29, P’31

Chair, Aspen Country Day School Board of Trustees

Friends,

I am writing to share that next year will be my last year as the Head of Aspen Country Day School. The 2026-2027 school year will be my 13th, and the timing just feels right for Rachel and me to move back East to be closer to our kids and our extended family. 

While leadership transitions are a natural part of independent schools, this community has become such an important part of my life. I will deeply miss the relationships I have built with colleagues, families, students, trustees, faculty, and my leadership team. 

Over the years we have accomplished so much together, including:

• A transformed campus and a spectacular physical plant made possible by completion of the $50M Known & Loved campaign.
• An exceptional faculty and staff, recruited with intention and sustained by a record-breaking Annual Fund along with the Teacher Wellness Fund, an incredible statement of support for teachers. 
• A robust financial picture, with an endowment of $12M, up from $325,000 in 2014; strong enrollment with 300 students today, up from 190 students in 2014; expanded access to faculty housing, with 13 units, up from 1 in 2014
• The $25M True to Tomorrow capital campaign fully underway, already building even more capacity for the school to achieve its dreams.
• Three landmark programs in academics, arts, and outdoor education that are among the strongest in the country. 

Most importantly, we have remained true to who we are, and students love coming to school, as you can see in the most recent State of the School video at this link. 

What I will carry with me most are not the buildings, programs, or milestones, but the people and relationships that define this school. I will remember greeting students each morning, being present at assemblies, performances and Blue/Green days, watching kids return from Outdoor Education trips more confident and resilient, and witnessing the powerful partnership between parents and teachers that defines this community.

Most importantly, I have tremendous confidence in the future of this school that we all love. Aspen Country Day is stronger than it has ever been. We have an excellent leadership team, committed trustees, a strong faculty and staff, engaged and supportive families, and some real positive momentum. The foundation is strong, and the future is bright.

I look forward to greeting all our returning families on September 8 and will remain fully engaged through June 2027. We are all dedicated to solidifying our gains, celebrating our thriving community, and preparing for a smooth transition. Thank you for your partnership over the last 12 years. It has been an extraordinary journey.

Josh