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Chris Winters to Serve GCDS as Head of Upper School, grades 9-12

Friday, July 27, 2018

July 26, 2018

Dear Stanwich Families,

As GCDS continues to build our high school program, with an eye toward a September 2019 opening, one of our highest priorities has been to find the individual with the experience, vision, and values to serve as our first Head of Upper School, grades 9-12. Starting last November, and with the assistance of Spencer Stuart, a premier executive search firm specializing in high priority administrative hires in secondary schools, we started a nationwide search. We reviewed 54 résumés, conducted phone interviews with 23 candidates, and met on campus with 7 outstanding candidates. Following the unanimous agreement of the Search Committee, comprised of trustees, faculty, and parents, the Board of Trustees is excited to announce the appointment of Dr. Christopher Winters to this position.

Since 2009, Chris has been the Headmaster of Greenwich High School (GHS), where his exemplary leadership has been held in high regard both within our local community and among national educational experts. During his tenure, GHS has been ranked among the top 2% of U.S. high schools by U.S. News and World Report and was also awarded Best Athletic Program in FCIAC in 2012, 2015, and 2018. Chris has received numerous fellowships and awards, including being named “Outstanding Principal of the Year” in 2014 and “Teacher of the Year” in 1995. At GHS, he has led a team of 12 administrators, 265 teachers, and 100 support staff members. Respected for his dedication to improving the learning experience for students and his support for fostering a collaborative culture for faculty, Chris is also known for his personal interest in each student. In addition to regularly attending athletic games and every school performance, Chris calls each student in the freshman class on his or her birthday for a one-on-one chat—more than 6,000 calls during his time at GHS. Even when leading a school with over 2,700 students, Chris has been dedicated to knowing and bringing out the best in each student.

Chris graduated cum laude with a B.A. in Political Science from Middlebury College. He received his M.A. and Ed.D. from Teachers College, Columbia University. An active member of our Greenwich community, Chris serves on the Board of the Boys and Girls Club of Greenwich, as well as The Greenwich Youth Services Bureau, and recently completed a three-year term as a member of GCDS’s Board of Trustees.

As a former GCDS trustee, Chris has a deep understanding of Country Day’s community and values. He believes that while education is about academic preparation, it is also about enabling children to develop a finely tuned moral compass. He is excited to join the dynamic team that includes Andy Ramirez, Director of College Counseling, and Tim Helstein, Athletic Director. Chris is a thoughtful leader and an inspiring public speaker, and he will be a guiding and motivating voice as we work together to create a high school for the next century.

I know you will join me in welcoming Chris and his wife Leigh to Country Day (please see his letter below). We will hold several receptions this fall so you can get to know Chris better. While you will begin to see Chris around campus immediately, his official start date will be October 1, 2018. We are thrilled that he will have the opportunity in the coming months to continue the significant work accomplished so far in building the high school program, hiring faculty, and working with architects on the design of new spaces.


Adam C. Rohdie
GCDS Headmaster

Dear Stanwich Families,

GCDS is a remarkable community, and I am deeply honored to join you as Head of the Upper School, grades 9-12. It is my past experience with GCDS (serving on the Board, working with Adam on different projects, and sharing common goals in educating young people) that drew me to this role. GCDS is about learning, engagement, creativity, and excellence. I share the values and expectations of our community and am thrilled to build on this foundation as we create what will become a nationally renowned high school.

For the past nine years, as the Headmaster of Greenwich High School, I have observed and appreciated the academic preparedness, personal integrity, and social responsibility of the GCDS students who join GHS. In the early stages of planning for the GCDS high school, we will identify the knowledge, skills, and dispositions that contribute to an integrated learning experience. We will lead with rigorous academics organized around courses in humanities, STEM, the arts, athletics, and other disciplines. We will challenge students to realize their highest academic strengths. We will know we are succeeding with each child as he or she demonstrates agency for deeply engaged learning. GCDS high school students will also be active on campus and in the community. Through teams, clubs, internships, and civic engagement, our students will develop an understanding of who they are, monitor their emotional and physical well-being, and contribute to their community.

Leading the new GCDS high school is a great opportunity, but leaving GHS is a difficult decision. I cherish the people there and the community of learning that we nurture. Ultimately, the singular opportunity—to lead the development of a new high school centered on GCDS values and the very best in educational thinking—is immensely compelling. My family is equally thrilled about the exciting opportunities ahead at GCDS. My wife, Leigh Shemitz, who is President of SoundWaters, is already thinking about extending possible seminars in environmental health and ecology. Our sons, Roger and Matthew, share in our family decision-making, and they have noted how genuinely enthusiastic I am for this challenge.

I look forward to meeting all members of the community, learning about your children’s interests, sharing with you my passion for education, and serving this wonderful community with humility, compassion, and unwavering faith in what we can accomplish together.


Christopher S. Winters

GCDS Head of Upper School, grades 9-12