Welcome New Faculty and Staff

As we ring in the 2023–2024 school year, we are pleased to welcome new faculty, administrators, and staff to The Winsor School, as well as some returning faces. While many are just beginning their Winsor tenures this academic year, you may already recognize some folks both from year’s past or who started working on campus last spring and over the summer. Please give a warm Winsor welcome to our newest community members! 

Joselyn Bengtson returns to Winsor after two previous temporary assignments working with the Business Office. Taking on a permanent position as bookstore associate, she has over 30 years of experience in benefits, benefit compliance, and employee leaves. Joselyn looks to bring humor and positive energy to all her interactions. She is a married mom of four, proud grandmother to 12 balls of energy, and a recent great grandmother to one little cutie. Joselyn came to the United States at the age of eight from the Dominican Republic. She enjoys family time, playing sports, Caribbean vacations, caring for her grands and dancing.

Julia Bielaski joins the Winsor community as an Upper School mathematics teacher. She is teaching Advanced PreCalculus to Class VII and Algebra 2 to Class V. Previously, she taught at the Cambridge Matignon School for several years and before that she was a research lab technician at Pfizer. Julia earned a Bachelor of Science in physics and mathematics from Clarkson University and is finishing her master’s in education with a concentration in STEM. In her free time, she watches horror movies, goes hiking, and travels to new places.

Lisa Brandorff returns to the Winsor community as assistant athletic trainer in an expanded capacity within the Athletics Department. Previously, she spent 11 years at St. Teresa’s Academy, an all-girls high school in Kansas, City, MO. Lisa earned her bachelor’s degree in secondary education in athletic training from the University of Kansas and her master’s degree in education from Tarleton State University. In her spare time, Lisa and her husband David enjoy classic Hollywood films and exploring New England with their rescue Boston Terrier, Friday.

Ivana Brown is excited to join Winsor as a Class I and Class III history teacher. She has spent the last two years teaching humanities to Grade 8th graders at the Shady Hill School in Cambridge and previously taught 6th grade history for ten years at St. John’s School in Houston, TX. Ivana has a doctorate in sociology from Rutgers University and taught a variety of undergraduate courses in sociology and women’s studies before realizing that working with middle schoolers was a lot more fun. Ivana enjoys middle schoolers’ humor, their growing sense of independence and interdependence on each other, and their willingness to explore new interests and activities. She loves teaching history as it helps students better understand the complex world around them. Originally from Slovakia, Ivana studied in the Czech Republic and has lived in New Jersey and Texas before coming to Massachusetts. She likes to travel, learn about new places and cultures, and spend time with her husband, two grown kids (when they visit), and their dog, Christie.

Janelle Browning joins the Winsor community as the director of strategic communications after 22 years in external affairs, communications, and marketing at Berklee College of Music. She earned her Bachelor of Arts in English from Truman State University and her Master of Arts in English and women’s studies from Colorado State University. In her spare time, she teaches yoga and tai chi, and is working toward her certification in yoga therapy. She shares her home in Medford with her partner and their three cats and three dogs. 

Brittany Bushman joins Winsor with over ten years of teaching and coaching experience and is beyond excited to join the Athletics Department. Coach Bushman earned her Bachelor of Arts in sociology from Emmanuel College and Master of Arts in coaching and athletic administration from Concordia University Irvine. At Emmanuel, she played basketball, softball, and threw the javelin. Brittany is also an MVP-caliber quarterback in the Women’s National Football Conference and has led the Texas Elite Spartans to four straight IX Cup Championships. She was named to the US National Team in 2013 and 2022 where the USA took home gold. When it comes to teaching, her experience is primarily rooted in science, most recently teaching Medical Interventions and AP Biology. She strives to make a positive impact on the young people she works with by building authentic relationships and passing on her knowledge and athletic experiences. She is proud to be an educator and coach and loves supporting student athletes and their dreams. 

Ann-Marie Ciaraldi is beyond thrilled to join Winsor this year and will be teaching all dance classes! A dance educator for almost 30 years, she most recently was on faculty at UMass Boston and Salem State University. In addition, Ann-Marie is a certified facilitator with the Dance Education Laboratory based in both NYC and at Jacob's Pillow in Becket MA. She holds a Master of Fine Arts in dance/choreography from Wilson College. Ann-Marie loves to see her students find their creative voices and thrive as they express themselves through movement. She resides in Beverly with her two children and Ramona the wonder dog.

Rachel Donnelly is excited to join Winsor as the assistant director of family engagement. Previously she worked at Bentley University in graduate admissions and at a number of independent schools as a social studies educator, facilitating learning for students in Grades 6–12. She earned her Bachelor of Arts in history and women’s studies from the University of Connecticut and her Master of Arts in secondary social studies education from Brown University. Rachel is passionate about building and celebrating community as an integral part of education and as a wonderful agent for lifelong learning and growth. When Rachel is not at work, she enjoys snuggling with her dog, Monti, crafting, cooking, reading, playing board games, and laughing way too loudly.

Theresa Evenson is excited to be returning to Winsor after teaching eighth grade science at The Hamlin School in San Francisco, California for the past three years. She is teaching Class III and Class IV Science, in addition to advising and working with Class III as one of the class coordinators. Theresa earned her Bachelor of Arts in biology from Bates College and her Master of Education from Lesley University. This will be her 26th year teaching middle school science, and she loves inspiring middle school students to explore different fields of science and to question the world around them. Outside of school, she enjoys gardening, cooking, reading, and traveling to new places.

Brianna Feliciano ’20 is excited to return home to Winsor as a technical theater assistant. Born and raised in a DIY family, she has always had an innate appreciation for design. She is currently pursuing her passion for architecture and set design at Tufts University. She finds joy in exploring various creative avenues and has, from a young age, created captivating multimedia artwork that reflects her unique perspective, spirit, and experiences.

Grace Gilmour joins Winsor's History Department teaching Classes II, III, and V. She returned to the Boston area in July after a decade of living in Vermont. Grace received her Bachelor of Science in secondary education specializing in history from the University of Vermont (UVM). She went on to teach world and United States history at Crossett Brook Middle School for seven years. While teaching, Grace earned her Master of Education in curriculum and instruction from UVM in 2022. Grace loves teaching adolescents. She adores their humor, growing curiosity about the world, and balanced need for support and independence. Grace believes that a deep understanding of history is necessary for a thriving democracy and is excited to facilitate nuanced discussions with her students at Winsor. In her free time, she enjoys collecting cookbooks, crafting, and traveling. 

Laura Iwanik is excited to join Winsor as the associate director of college counseling. Most recently she worked in college admissions at Harvard University and Georgetown University. She began her career in education as a high school history teacher before transitioning to college admissions. Now, after eight years working in higher education, she is excited to be part of an independent school community again. Laura holds a Bachelor of Arts from Mount Holyoke College, a Master of Arts in teaching from Brandeis University, and a Master of Education in education leadership from the Harvard Graduate School of Education. She lives with her husband, two young children, and a playful puppy.

Shannon O'Brien joined the Winsor community in April 2023 as the assistant director of admission. She holds a bachelor’s degree in business administration from Hotelschool the Hague in the Netherlands, and a master’s degree in international human resources management from Rome Business School. After working in HR in the hotel industry, she took a role at a study abroad organization and was immediately inspired by working with young people who were so dedicated to pursuing educational opportunities. After nearly 10 years abroad, Shannon returned to her home state of Massachusetts. She is thrilled to be working in an educational setting once again. In her free time she loves reading novels and attempting new recipes in the kitchen. 

Lauren Parker joins the Winsor community in the Advancement Office where she serves as the advancement assistant. She holds a Bachelor of Arts in both English and political science from Indiana University and a Master of Science in political science from the Massachusetts Institute of Technology, where she focused on the intersection between politics and public health. Originally from Indiana, Lauren makes her home in Brookline with her spouse and high school sweetheart, Evan, and two ornery kittens, Nickel and Dime. In her spare time, she reads voraciously, knits and embroiders passably well, and bakes often!

Claudia Peña Fermín is thrilled to join Winsor as a Lower School Spanish teacher. A passionate and dedicated educator with 18 years of experience at all grade levels, her vast experience includes public institutions, independent schools, as well as higher education in various regions of the United States, including Puerto Rico. Claudia holds a Master of Arts in Spanish linguistics from Cleveland State University. She loves to share the unique aspects of the Spanish language and culture with her students to broaden their perspective about the world. Claudia recently moved to the beautiful Boston area with her husband. In her free time, she loves to explore new places, travel, and spend time with her loved ones. 

Mariselis Powell joined the College Counseling Office as the new College Counseling assistant in December 2022. Previously at The Park School, she served in several roles, most recently as the administrative assistant in the school's library. A graduate of Boston University, Ms. Powell has also worked in various capacities at other local independent schools, including the Brooks School and Phillips Academy Andover. She is experienced in dealing with standardized testing issues, college financial aid forms and processes, and even service programs, and special summer opportunity programs. Ms. Powell and her family spent a number of years living and working at The Cate School in California, where she worked as an administrative associate in the College Counseling Office.

Sylvi Re joins Winsor as a semester-long maternity replacement working as a costume teacher and designer. She has previously done maternity leave coverage in the costume shop and Department of Theatre at Northeastern University, and also spent four years with the Boston Ballet costume shop working in various positions. She received her Master of Fine Arts from Carnegie Mellon University in costume production and management. She is very excited to be teaching again and looks forward to the shows coming up this semester. She lives in Belmont with her husband, baby, and two amazingly tolerant 19-year-old cats.

Jess Schwinn joins Winsor as the database administrator for the Advancement Office. She comes from just down the block at Emmanuel College where she worked as a gift processor and database associate. Jess earned her Bachelor of Arts in sociology/criminology from Emmanuel College in 2019 and is currently obtaining her Master of Business Administration there as well. She loves all things data and considers it a great day when she successfully learns a new Excel formula! She currently resides in Brighton with her partner, their two cats, and dog.

Jessica Wang joins Winsor’s Upper School Mathematics Department as a Precalculus and AP Calculus teacher this year. Prior to arriving at Winsor, Jessica taught Upper School math at Milton Academy where she also coached volleyball, advised the school’s Asian culture and affinity club, and helped support the residential life program. Jessica holds a Bachelor of Science from Duke University and a Master of Education from the University of Pennsylvania. Jessica grew up in the Chicago suburbs and currently lives in the South End with her partner Jack and dog Charcoal. In her free time, she enjoys working on puzzles, rock climbing, and traveling the world—27 countries and counting! 

Becky Withiam joined Winsor in late September 2022 taking on the new role of director of engagement and events in the Advancement Office. She brings more than 15 years of experience specializing in alumnae affairs, engagement strategy, and event management at Harvard University including nine years at the Harvard Radcliffe Institute. She earned her Bachelor of Science in organizational communication, learning and design from the Park School of Communication at Ithaca College and her master’s degree in management from Harvard University. Becky lives in Watertown with her husband and two young children.