Associate Head of School Kate Caspar’s experiences as a student—in the classroom as well as on the athletic fields and courts—had a lasting influence on her approach to her work at Winsor. She remembers being challenged and encouraged by trusted teachers to do more than she had thought possible, and strives to be a thoughtful, trusted mentor for her own students.

A varsity basketball, soccer, and lacrosse player in high school, she went on to play intercollegiate lacrosse at Stanford, garnering MVP as a junior and leading as captain her senior year. Her time as a member and leader of teams helped her develop an understanding of the importance of group dynamics, and bolstered her ability to manage individuals with different skills and personalities while maintaining the highest standards.

Kate’s career in education has spanned a number of roles across four independent schools. Initially an English teacher and assistant director of athletics at the Kent School, she later shifted her focus to become director of college counseling at the Westminster School, where she spent over a decade guiding students through the process of considering their next academic steps. She found additional opportunities at the Pomfret School, where she served as academic dean and assistant head for academics. Throughout her time in these varied roles, she counts herself fortunate to have had the consistent opportunity to continue teaching.

Kate arrived at Winsor in 2014 to serve as assistant head of school, and was named associate head in 2016. She feels fortunate to serve as both an administrator and faculty—she teaches Upper School English—and appreciates how Winsor’s small size means we are able to know and invest in our students as individuals. She loves to be among a faculty of teachers “so committed to constantly learning, who want to learn, and who will likely retire as curious about new teaching methods as they were when they first arrived at Winsor.”

Kate’s favorite quote comes from Henry David Thoreau: “To affect the quality of the day, that is the highest of the arts.” She believes that to have even a small effect on one human is an art, and at Winsor, she aims to do that every day, and inspire her colleagues and students to do the same.