Welcome New Faculty and Staff

The Winsor School is pleased to welcome new faculty, administrators, and staff to our community. A few joined us last spring and summer, so you may already recognize their names. The rest began their Winsor tenures during our school opening this academic year. Please give a loud Winsor welcome to our new community members! 
Sammi Arnold comes to Winsor as assistant to the head of school. Previously, she worked at Mass Audubon, as assistant to the president and corporate secretary for the board of directors. She graduated from Boston University in 2018 with a dual degree in English and classical civilization. Since then, she’s held various positions across different sectors, working as a horseback riding instructor, museum exhibitions intern, administrative assistant, marketing coordinator, and even pest control service technician. Sammi has always had a passion for education, and she will finish her master’s degree in museum studies and nonprofit management from Harvard Extension School in 2024. She splits her time between cuddling her cat, Dante, at her home in Auburndale and riding her horse, Sam, at a farm in Holliston.
Erin Cantos is a new member of Winsor’s history faculty, where she will teach Class V history and electives. She previously taught for three years at Colorado Academy in Denver, including courses on contemporary world history, empire and revolution in Southeast Asia, and the Arab Spring. Erin recently received Ph.D.s in Southeast Asian history and educational policy studies from the University of Wisconsin-Madison. She has lived and worked overseas, including a yearlong stint in the Philippines for her dissertation research on radical 19th-century Indigenous educators and the Philippine Revolution. A Chicago native, Erin has a deep love for her neighborhood hot dog stand, Lake Michigan, and the Newberry Library. 
Laura Christian joins the Winsor community as the director of annual and leadership giving. She most recently served as a major gifts officer at Roger Williams University and the senior director of development at Boston Children’s Museum. Prior to the museum, Laura spent eight years as the director of the Wellesley Fund at Wellesley College. Laura received a B.A. in sociology/psychology from Middlebury College and an M.Ed. from Lesley University. In her free time she likes to bake, go fly fishing, and spend time with her family.
Ellen Crowley is Winsor’s new teaching and learning specialist, and she will be the assistant coach of the varsity soccer team this fall. She spent the last five years as a learning specialist and multiseason coach at the Noble and Greenough School, which she also attended as a student. Ellen earned her B.A. in secondary education and history and her M.Ed. in moderate disabilities at Boston College. She is a board member of the Corey C. Griffin Foundation, and in her free time she enjoys spending time with her seven nieces and nephews or getting outside to play golf or pickleball. 
Essence Denton joins Winsor as the advancement assistant. She graduated from Pine Manor College with a degree in psychology and special education. She fell in love with Boston after attending college here, but she is originally from Chicago and travels to her hometown to see her older brother every chance she can. During her free time, she likes running races, listening to live music, dancing, and anything creative.
Laura Duncan joins Winsor as the director of the Virginia Wing Library after eight years at the Upper School library of Buckingham Browne & Nichols. She lives in Somerville with her husband and two cats, and she can frequently be found curled up with a good book, fussing over her houseplants, traveling to far-off places, or learning a new hobby (currently, embroidery). She is delighted to join Winsor’s community of readers! 
Maddie Edwards joins Winsor as a member of the Lower School Mathematics Department teaching Class I, Class III, and Class IV. She spent her last three years as a middle school math teacher at Excel Academy. Originally from outside of Columbus, Ohio, Maddie earned a B.S. in elementary education from Skidmore College, then moved to Boston to get her master’s in mathematics curriculum and teaching from Boston University. She lives in Revere, where she loves walking along the beach, tending to her very small garden, playing board games with her roommates, and cuddling with Toby (her roommate’s new cat).
Maura Flanagan joins Winsor as the new director of rowing. Previously, she was the program coordinator and head coach at the Narragansett Boat Club. She found her love of rowing at St. Mary Academy-Bay View, went on to row at Fairfield University, and has gained coaching experience at programs along the East Coast for the past six years. She is excited to bring her passion for the sport to the well-established Winsor crew program.
Madeline Giglio joined Winsor in December 2021 as assistant director of annual giving, after two and a half years at Brigham and Women’s Development Office. Madeline graduated from Boston University in 2019 with a degree in health science and a minor in business. After three years in the North End, she is making the move to Southie. In her free time she enjoys workout classes, live music, and cooking. 
Katherine Hancock joins Winsor as the Virginia Wing Library’s pre-professional librarian after spending the last year as an elementary school librarian in the Northeast Kingdom region of Vermont. Before becoming a librarian, Katherine served in various environmental organizations in rural Vermont and in Jackson, Wyoming, through AmeriCorps. Originally from Atlanta, Katherine received her B.A. in English literature from Rhodes College in Memphis and is excited to start her master’s in library and information science at Simmons University this fall. When she’s not reading, Katherine enjoys cooking, walking and hiking, camping, and spending time with loved ones.
Madeline Holtz joins Winsor as a chemistry and STEM teacher, having previously taught chemistry at the Boston Latin School. Originally from San Francisco, Madeline moved to the Boston area to study chemistry and media studies at MIT (she still lives in Cambridge). In her free time, she can be found jogging, reading, playing music with friends, and complaining about New England weather. 
Jojo Kendale joins Winsor as an Upper School chemistry and physics teacher. After living in New York City for 10 years, she moved back to her hometown of Cambridge in 2020 with her husband and two young daughters. In New York, she spent two years as an organic chemistry adjunct instructor at NYU, followed by seven years teaching 10th grade chemistry at Columbia Grammar & Preparatory School. Last school year she taught chemistry at the honors and AP levels. She is excited to be part of the Winsor faculty (a longtime career goal). She loves day hikes, live music, board games, and science dresses.
Michael Mirelman joins Winsor as a member of the Upper School history department. He recently moved to Watertown from Pittsburgh, where he taught U.S. history and coached squash at Shady Side Academy. He has 16 years of experience working in independent schools. Michael received his B.A. in political science and Spanish at Emory University and his master’s in education policy, organization, and leadership from Stanford University. After graduate school, Michael served as a founding teacher of the East Bay School for Boys in Berkeley and as department chair of humanities at the Jewish Community High School of the Bay. Outside of school, his interests include hiking, cycling, cooking, and traveling. 
Maia Monteagudo ’06 rejoins the Winsor community as the full-time school counselor. She has been working with the Lower School and Upper School since January. She graduated from Connecticut College with a B.A. in psychology and received her master’s in mental health counseling with a concentration in expressive arts therapies from Lesley University in 2017. Maia brings with her an enthusiasm and respect for the intersectionality of mental health needs within the Winsor community. In her spare time, Maia creatively explores mental health and cultural identity themes through acrylic painting and unconventional art materials. 
Emily Monteiro returns to Winsor as the school counselor to serve Lower School and Upper School students. Since graduating from Boston College with a master’s in clinical social work, Emily has worked in public schools in various roles including alumni services, college counseling, operations, and as a dean. Emily lives in Bridgewater and enjoys spending free time with her husband and 8-year-old daughter. 
Annie Murray joins Winsor’s mathematics faculty with 19 years of experience teaching upper school mathematics, most recently at an all-girls school in Baltimore. She returned to the Boston area in spring 2021, after a hiatus of many years, to be closer to family. As a teacher, she wants to get students to think like mathematicians and enjoy the beauty and challenge in problem solving and modeling the real world with mathematics. She studied engineering at MIT and worked in industry for several years before changing careers to become a teacher. She has three daughters and two grandsons who live in the Boston area, and a son who lives in Seattle. She enjoys crossword puzzles, counted-cross-stitch embroidery, crocheting, reading novels, and learning about local history. She lives near North Station with her husband and is happily riding the Green Line to work.
Lauren Proll will be teaching two sections of Class V in the English Department this coming year. She recently retired from Boston University Academy, where she taught 10th and 12th grade English for 14 years in addition to advising the school literary magazine. Before BUA, she served as chair of the English Department at Gann Academy in Waltham. Lauren began her teaching career at Indiana University, where she earned her Ph.D. in English with a focus on late Victorian and modernist British literature, particularly the novels of D. H. Lawrence. After graduate school, she taught English and directed the writing program at Wittenberg University in Ohio. Lauren’s passions include great books, gardening, travel, BBC murder mysteries, and the New York Times Sunday crossword. (She also spends far too much time on Spelling Bee and Wordle.) Lauren lives in Newton with her husband, William, and their two pesky and pampered tabby cats.