Welcome New Faculty and Staff — 2025
As we kick off the 2025–26 school year, we are excited to welcome new faculty, administrators, and staff to the Winsor community. While many folks are just beginning their Winsor tenures this academic year, some familiar faces started working on campus last spring and over the summer. Please give a warm Winsor welcome to our newest community members!
Sarah Cormier: Director of Annual Giving
Sarah Cormier is thrilled to join the Winsor School as director of annual giving. She received her bachelor of arts from Simmons University and master of public administration from Clark University. She brings over two decades of fundraising experience, most recently at Harvard University. In her free time, Sarah enjoys running, spoiling her godchildren, and fostering dogs. She lives in Northborough with her husband Jamie, their dogs Nigel and Winston, and cats Erebus and Jasper.
Taylor Crompton: Lower School English Faculty
Taylor Crompton is so excited to join Winsor’s wonderful community as an English teacher. Proudly born and raised in Indiana, Taylor received a bachelor of arts in economics and English literature from DePauw University before moving to Washington, DC for graduate school. After graduating from Johns Hopkins University’s School of Advanced International Studies with a MA in international relations and finance, Taylor embarked on a brief corporate career that took him to NYC. From a long line of educators, Taylor found his way back to the classroom in 2020 as a Teach for America corps member in rural Idaho. Taylor and his partner will be living in the Fenway area. They’re more than excited to explore local running routes, try new restaurants, and build community in their new neighborhood!
Julia Cunningham: Assistant Director of Admission
Julia Cunningham is joining Winsor’s community as the assistant director of admission. Originally from Middletown, CT she is thrilled to return to New England after spending her recent years in Dallas, TX. She earned her bachelor’s degrees from Southern Methodist University where she graduated summa cum laude as a double major studying both psychology and sport performance and leadership. She has previous experience in both high school and undergraduate admission and, as a girls’ school graduate herself, is so excited to enter Winsor’s environment. She currently lives in Brookline with her partner and in her free time enjoys going to the beach, cooking, and wandering Trader Joe’s.
Jason Curtis: Director of Technology
Jason Curtis is excited to join the Winsor School as the director of technology and do all he can to empower and support students as they navigate an increasingly complicated world. A veteran of girls’ schools, he has been either the director of technology or the chief technology officer at Houston Christian High School, Laurel School (Shaker Heights, OH), The Hockaday School (Dallas, TX), and Thaden School (Bentonville, AR). As a father of two girls (and one son), he cares deeply about girls’ education and supporting the development of strong, independent young women. He has a cat named Taylor Bell and in his spare time likes to hike, camp, and fix up vintage electronics.
Leigh Hadaway: Lower School History Faculty
Leigh Hadaway joins the Winsor community as a Lower School history teacher and Class III advisor. She received her bachelor of arts from Berry College and master of arts from Pace University. Originally from Georgia, she moved to Boston from Washington, DC, bringing six years of experience working in boarding and day schools. She is passionate about mentorship to girls and is excited to teach in an all-girls’ environment. Outside of school, Leigh lives in Cambridge with her partner and enjoys kayaking, exploring Boston, and going on hikes with her dog, Blue.
Leila Huff: Learning Specialist
Leila Huff joins the Winsor community as a learning specialist and Class II advisor. Originally from New York, she moved to Boston after earning her bachelors of arts from Villanova University and her masters degree from Middlebury College. Leila brings over thirteen years of experience working in independent schools and is excited to return to an all-girls’ environment—something she personally valued during her own high school years. Outside of school, Leila enjoys spending time with her family and exploring new restaurants in and around Boston.
Gregory Juste: Facilities
Gregory Juste is a dedicated member of the Winsor community who joins the Facilities team. He has a strong background in service and hands-on problem-solving. A former U.S. Army combat engineer, he spent nine years in the military and was deployed to Kuwait, Iraq, Lithuania, and Germany. Now based in Boston and a proud father of three, Gregory brings discipline, resourcefulness, and heart to everything he does.
Chelsea McNeil: Archivist/Library Assistant
Chelsea McNeil is thrilled to join the Winsor School as archivist/library assistant. After growing up in California, she earned a bachelor of arts degree in English. In 2025, she graduated from Simmons University with a master of science in library and information science. For more than seven years, Chelsea has worked across various library, special collections, and museum environments, and she is so excited to be a part of the Winsor community. Chelsea resides in Malden with her partner, her cat, and her dog. She enjoys hiking, cooking, and going antiquing.
Raquel Sanchez: Spanish Faculty
Raquel Sanchez joins the Winsor community as a Spanish teacher in both the Lower School and the Upper School. Originally from Valencia, Spain, Raquel holds a bachelor’s in journalism and communications, and a master’s in international politics. Her passion for language and culture has taken her around the world—she has taught Spanish in French Guiana, France, and Thailand, which brings a global perspective and multicultural experience to her classroom. Raquel moved to Cambridge last year with her husband and her cat, and is excited to continue sharing her love for the Spanish language with the students of Winsor. In her free time, she enjoys hiking, baking, and spending time with a good book—often thanks to the excellent selection at the Cambridge Public Library.
Sabrina Weissbach: Wellness Department Head
Sabrina Weissbach is thrilled to join the Winsor School as both the Wellness Department head and Classes I–VII health teacher. Sabrina brings 15 years of experience working and leading in independent schools. Sabrina grew up and spent most of her career in New York City where she served in the roles of school nurse, health educator, and director of athletics at The Calhoun School. Sabrina completed a master of education in private school leadership from the Klingenstein Center at Teachers College, Columbia University, earned a master of science in athletic administration and coaching education from Ohio University Patton College of Education, and holds a bachelor of science in nursing from New York University College of Nursing. She is also a licensed registered nurse. Sabrina lives in Andover with her wife who is a dean of students at Phillips Academy Andover. You can catch her reading, traveling, or working in her garden.
