Head of School Search

Letter from Chris Sandford, Head of School

Dear Woodstock Academy Community:

After much reflection and consideration, I am writing to announce my retirement from The Woodstock Academy at the end of the 2024-2025 school year. I arrived at The Academy almost eleven years ago, and over that time, this community has become more than just a workplace to me. This community has literally become my second home and has filled my life with cherished memories and meaningful connections. 

Serving as the Head of School at The Woodstock Academy has been a great honor and privilege. When I depart the role on June 30, 2025, I will have reached the point of being the 4th longest serving school leader in the history of The Academy and completed my 25th year in education overall. This would not have been possible if not for a supportive board, staff, and larger community. I would be remiss if I did not thank Christine Swenson, who has served as President of the Board of Trustees during my tenure. She has been an outstanding and supportive partner on this journey. In addition to Christine, I have had the privilege of working alongside other dedicated board members, passionate colleagues, supportive families, and, most importantly, inspiring students. Together, we have navigated through challenges and celebrated numerous achievements. But, through it all, we worked to make the lives of our students better each and every day.

The Academy has evolved in many ways over the past ten-plus years. As with any historic institution, it must change, grow, and respond to the world in which it finds itself. I am incredibly proud of what we have accomplished together. We transitioned to a one-to-one learning environment; we weathered a global pandemic, expanded to a two-campus model, built an advancement office, established the Loos Center for the Arts, created countless student opportunities, remodeled the historic Academy Building, and increased the endowment by more than 300%. But, if I were asked what I am proudest of, I would say that The Academy has developed into a very inclusive and accepting environment where students feel safe and cared for while increasing the diversity of the students and staff.

I often speak about how each school leader writes a chapter in the history of a school. Some chapters are short, some are long, some are full of accomplishments, and some are not, but each leader should leave the school in a better position than when they arrived. I believe that together, we have provided the next leader with a strong foundation so they can write their own chapter in the history of our beloved school.

As I prepare to embark on this new chapter in my life, I want to express my heartfelt appreciation to each of you who have made my journey at The Academy so memorable. Your kindness, encouragement, and unwavering support have been the driving force behind my dedication to our shared mission of nurturing young minds and fostering a vibrant learning community.

While I will miss the daily interactions with students, colleagues, and alumni, and the sense of purpose that comes from being a part of The Academy, I am excited about the possibilities that lie ahead. Retirement will allow me to pursue personal interests, slow down, and explore new opportunities.   

I am excited to continue being a part of The Academy community for the next twelve months, and I am confident that the search committee will successfully complete its work and find the right school leader to take The Academy’s strong educational community to the next level. 

Thank you for your support and friendship throughout the years. I am honored to have served The Academy community and will forever cherish the memories we have created together.

Sincerely,
Christopher Sandford
Head of School

Search Committee Members

Christine Swenson P '03, '10, '14, (Chair), President of the Board of Trustees & WA Foundation Director
Edwin Higgins P '02, '05 '10, Vice President of the Board of Trustees
Martha Beckwith ’80, P '04, '05, '08, '12, Alumni Trustee
Hans Rhynhart ’89, P '20, '22, Alumni Trustee & WA Foundation Director
Leisl Langevin ‘04, Alumni Trustee & President of the WA Foundation
Eric Quinn P '16, '17, Trustee of the Community & WA Foundation Director
Melany Gronski P '19, '21, '25, Science Faculty
Patrick O’Brien ’97, P ’24, ‘25, ‘29, Alumni Advisory Council Member
Jonathan Sturdevant, Associate Head of School for External Affairs

Response from Christine Swenson, President of The Woodstock Academy Board of Trustees

On behalf of The Woodstock Academy Board of Trustees, I first want to thank Chris for his extraordinary leadership as the Head of School at The Academy over the last 11 years. During that time, he has advanced countless improvements for the institution, of which his letter only touches the surface.

Eleven years ago, we set out to find a Head of School who was a visionary educational leader, with superb soft skills who would embody the values of the institution and would live and breathe The Academy. We are tremendously grateful that Chris accepted the challenge and joined us on what has been an amazing journey. Collaboration was his guiding principle in the pursuit of new opportunities or resolution of challenges. His natural ability to combine big picture perspective with detailed execution, genuine caring, and tireless dedication have been truly transformative and will leave a lasting impact. Most importantly, Chris has been a fearless advocate for our students, placing their benefit and well-being at the forefront of his efforts.

We are forever indebted to Chris for his service and dedication to The Academy and while we are sad to see him go, we wish him all the best in his retirement. He will leave The Academy exceptionally well-prepared to continue progressing forward.

I want to assure The Academy community that we will be working diligently to find our next Head of School. I will personally oversee this process, which is just beginning, and you will hear more about it in the coming months.

The Board and I are beyond proud of what we have accomplished together with Chris at the helm and are excited as we begin to write the next chapter of Woodstock Academy’s future.

Sincerely,
Christine Swenson
President, The Woodstock Academy Board of Trustees