Soon after Sarah Pelmas arrived at the Winsor School in 2016, she sat in the third floor of the Virginia Wing Library, where the portraits of the former heads of school hang. She said the moment felt a little bit like sitting in the office of Professor Dumbledore—the head of the

Hogwarts School in the fictional Harry Potter series, its walls lined with portraits of the school’s

prior leaders. Except unlike the likenesses in the paintings with whom Dumbledore could converse, Ms. Pelmas—Winsor’s eighth head of school—was left to imagine what her predecessors might have said. “I was a little jealous of Dumbledore because he could talk to them or ask them advice,” she recalls.

Lack of access to wizardry notwithstanding, Ms. Pelmas has returned to the spot again and again, drawn in by the connective thread the women leaders have passed on, and imagined herself in communion with them.

“Sitting in the third floor of the library is a very glorious thing to do, looking at the tenures of the people before me, and knowing how human they are, how they took on this mantle of stewarding this institution that precedes you and will succeed you,” Ms. Pelmas reflects as she prepares to leave her post after nine years. “I have thought, what did they do, what did they accomplish, and given the moment they were in, how did they make their way? And what could I take from that in moments I have found difficult so that I could make sure that we were moving forward in the best way possible? It’s just a moment in time and your job is to take the very best care of the school that you possibly can, and improve upon it as best you can and then hand it off to the next person to do the same thing.”

By all accounts, Ms. Pelmas has done just that. She has upheld and strengthened the founding principles of the school to provide girls an excellent, well-rounded education. She is lauded for building community; establishing the Wellness Department; launching Winsor Leads, the school’s historic $100 million comprehensive endowment campaign; championing the independent school model; and shepherding the 139-year-old institution during a period that saw two divisive national elections and a global pandemic. She will also be remembered for her genuine curiosity about people; her warmth, sense of humor, and approachability; and as an inspiration to Winsor girls.

In recognition of Ms. Pelmas’s leadership and legacy, a chorus of former and current educators and administrators, parents, alumnae, and students has weighed in on the legacy Ms. Pelmas will leave.

A Leader Through Challenge

World events during Ms. Pelmas’s tenure posed unique challenges, and what she referred to as the “significant headwinds we’ve been facing at all times.” But as Kate O’Donnell ’05 shared, “Winsor has always had the perfect head of school at the perfect time, and Sarah has been no exception. No one could have led us through the last few years like she has. She came into Winsor ready to go, and was immediately accepted and embraced by the community. She’s warm, a fierce advocate, crazy smart, and one of the funniest people I know. And above all, I love that she doesn’t take herself too seriously—which lends more gravity to situations when she needs to be [serious].”

Many praised her response to various challenges, particularly to the 2016 election and the pandemic. Ms. Pelmas called an impromptu all-school assembly in the wake of the election results as a way to acknowledge that many students were struggling during this divisive time. “Her comments were clear, resolved, honest, supporting, and empowering for our daughters, and we believe many other students,” note Hal Burstein P’18, ’21 and Mary Mullen P’18, ’21.

Former faculty Jennie Skeele ’71, P’98, ’02 was impressed with how Ms. Pelmas conveyed her support without getting political. “She didn’t say how she felt, but she implored everyone not to lose sight of who we are as a community.”

Meanwhile, when the pandemic hit, Ms. Pelmas rapidly moved to protect the health and well-being of the students, but she also recognized the importance of in-school education, Mr. Burstein and Ms. Mullen recall. “With her team, she led an early return to school with appropriate safety features, and was ahead of the curve in comparison to most peer schools.”

Karen Geromini, Winsor’s chief operating officer, credits Ms. Pelmas for her vision to prepare Winsor for a possible closure due to COVID-19. “Very early she developed a plan to educate and teach the faculty and staff how to keep teaching and business operations going even though the school would not be held ’on campus.’ She was the mastermind in developing the COVID opening plan, putting in place strategic initiatives for the senior leadership team,” she says. “In particular, she showed me what the power of perseverance and determination looked like. We were all so vulnerable and not once did she waver from the goal of keeping as much normalcy to our school day/year as possible. Her actions demonstrated compassion and empathy to all families and employees who were struggling during this time.”

Rachel Stettler, Winsor’s seventh head of school and Ms. Pelmas’s immediate predecessor, summed it up: “I thought how she led the school through the pandemic was a sign of such wise decision-making and crisis management. From all reports, Winsor handled that time as well as could be imagined.”

In the wake of these unprecedented circumstances, Ms. Pelmas rose to the challenge.

“The election(s) and the pandemic were arguably the most important things that happened to our country and to Winsor and its families during her tenure as school head,” Mr. Burstein and Ms. Mullen say. “Challenging times can make for great leaders. Sarah Pelmas proved that in both instances.”

Denise Labieniec, institutional researcher and science faculty, would agree. “Sarah’s headship has spanned a really unique time in independent schools where everything has been questioned,” she says. “She led the school through a time of tremendous political vitriol, a pandemic, a racial reckoning, shifting ideas about gender and what it means to be a ‘girls’ school,’ and challenges to the paradigm of education post-pandemic. This has not been an easy time to lead a school, and I think Sarah’s intellect and venturesome leadership have made her a head for these times.”

A Champion of Independent Schools

While leading Winsor, Ms. Pelmas’s impact has extended beyond the school. Indeed, she appreciates the wider network of independent schools to which Winsor is linked. “As a leader for AISNE [Association for Independent Schools in New England] and the 1911 group [a professional learning community for heads of school], Sarah has worked hard to make sure these organizations are there to support independent schools across the country,” says Jennifer Price, head of school for Buckingham Browne & Nichols (BB&N). “She is

a leader among leaders.”

Noting her affiliation with AISNE as well as other professional groups including the Eastern Independent League (EIL), New England Association of Schools and Colleges (NEASC), Independent School Data Exchange (INDEX), Heads and Principals Association, the Heads Collegiate Forum, Greg Schneider P’25, Belmont Hill’s head of school and parent of a Winsor student, says: “Sometimes I wonder if the Winsor community knows just how well-

regarded Sarah is across the region and country.”

“Sarah doesn’t always feel the need to be the loudest voice within these groups, but when she does speak, everyone listens,” he continues. “Her clarity of values and sense of purpose as an educator have  continued to build the reputation of Winsor nationally through her wise presence in many venues the Winsor community never sees. I know that this unseen professional community wishes Sarah nothing but great success and happiness in her new endeavors after Winsor.”

Lisa Pullman, founder and executive director of INDEX, credits Ms. Pelmas’s contribution to the organization. “She has been an unwavering supporter of INDEX through her active engagement in our meetings, her thoughtful contributions, and her willingness to step forward and lead conversations that have led to a deeper understanding of shared challenges among our network for schools. Her support of our mission and her belief in the power of our network have strengthened our organization.”

Geoff Wagg P’18, ’20, ’22, head of Waynflete School, sees Ms. Pelmas’s influence as extending beyond Winsor and contributing to the broader educational community. “She has not only elevated the school’s prominence nationally, but has also been a mentor to other heads of school, embodying the qualities of a true leader among leaders,” he says. “Sarah is someone other educators seek out.”

Indeed, Ms. Pelmas led the charge to establish one of the first endowed chairs in a secondary school or college to create a diverse and inclusive community. Carolyn Peter, Winsor’s sixth head of school, remembers the conversation she had with Ms. Pelmas that was a critical step in creating that chair—the Bezan Chair for Community and Inclusion, which was first awarded to Director of Community and Inclusion Julian Braxton in 2022.

“The Bezan Chair is a statement of Winsor’s independent school leadership that was celebrated at a dinner attended by former heads of school, current and former faculty, and leaders in the field of inclusive education,” Peter says. “Creating the Bezan Chair is an example of the lasting impact of Sarah’s leadership at Winsor.”

An Ardent Supporter

Ms. Pelmas is praised for being unwaveringly supportive, whether professionally or personally.

Head of Upper School Kim Ramos appreciates the support Ms. Pelmas has extended. “As a faculty member and administrator, I greatly appreciate the way Sarah is willing to support an idea or initiative I want to try and to give me the confidence, guidance, and support to let me navigate it. …Sarah encourages us to say yes whenever possible and to focus on what could be, without getting caught in the weeds or stuck on what might be difficult. She has encouraged us to be creative, innovative, and brave, and I think her encouragement has helped shift the culture and community at Winsor.”

Denise Labieniec recalls going to Ms. Pelmas for counsel when she was considering a career change and stepping out of administration. “Rather than simply accept that decision or convince me to stay in my role, she let me know how much she valued my perspective on the admin team and invited me to envision a different role. She noted that I enjoy reading and research and conceptual strategic thinking, and she created the position of institutional researcher for me,”

she says.

Jennifer Price, BB&N’s head of school, recounts Ms. Pelmas being there for her during treatment for breast cancer. “Sarah was there every step of the way to support me. So much so, that once a week after treatments at Dana Farber I would make my way over to Winsor and sit with Sarah on the Adirondack chairs and drink a Spindrift. …Sarah just knows how to be there for you. She just shows up. She is real. And she truly cares.”

For Kristin Bennett ’85, Ms. Pelmas embraces causes that are important to her. “Sarah’s endless support of equity and justice, wonder and adventure, and support for women’s voices are the reasons I will make my donation to Winsor for an Endowed Chair for Women in Science in my will. Like Miss Wing, Sarah is the epitome of personal courage and encouragement for us all.”

A Head with Heart

Ms. Pelmas has led with compassion and an open door. In fact, many

recount how her warmth and empathy made them feel seen and understood. From students, faculty, and administrators to alumnae and parents, she has proven to be a genuine people person and a present leader, attending sporting events, choir concerts, and academic programs with equal enthusiasm.

When Ms. Pelmas joined the Winsor family, Kate Baker-Carr ’80 was immediately impressed with how fluidly she “moved through the corridors, classrooms, playing fields, and the dining room greeting one and all by name.”

“I marveled at the rapport she created as she interacted with members of the school,” she says. “She knew something about each person. How quickly Sarah joined the community and appreciated the rhythm of the Winsor day.” And the conversations have flowed both ways. Christopher Andrews P’26, an ex officio Winsor trustee, notes that when Ms. Pelmas walks through the school, students stop to talk to her and vice versa.

“She might call out their performance in a recent cross-country race or a choir concert or a piece of their art she really liked,” he says. “And the students are able to talk to her about their days, their opportunities, and their hopes for the school. I know Sarah welcomes and cherishes these interactions. They set the tone for the school and send a message that being part of Winsor is being part of a community—a community where everyone will be seen, recognized, and encouraged.”

English faculty Susanna Ryan sums it up this way: “Sarah has a way of making others feel held, metaphorically.” That includes Ms. Ryan herself. “Whenever we meet, she always puts me at ease and focuses her gentle but keen attention squarely on our conversation…and somehow Sarah always demonstrates not only interest but a kind of gracious empathy.”

Student Anya Weerapana ’25 says this attentiveness extends to everyone—from students to parents to faculty and staff. “Ms. Pelmas thrives off making people feel heard. It’s not just on the sports sidelines, either; [it’s also] in her office listening to a group of seniors carol and beg for a snow day (and then granting one!) and in her well-thought-out speeches when giving faculty awards.”

Katherine Danik ’25 is still in awe of the sight of Ms. Pelmas talking to so many people while walking the halls, and acknowledging her by name as well when she was a Class I student. “This was just one of the many moments where Ms. Pelmas went out of her way to know everyone around her, working hard to welcome new Class I students to the school.”

Nidhi Mallavarapu ’25 says Ms. Pelmas “genuinely cares about celebrating everyone’s victories and showing up for the pivotal moments in their Winsor career.” Nidhi, who has sung in Winsor choirs since her time as a Lower School student, recalls Ms. Pelmas being in attendance for nearly every concert. “She’s always moved to visible emotion by what we sing, and to

me, that shows how proud she is of her students.”

Jemma Kuriyel ’25 remembers Ms. Pelmas offering a tour of Winsor’s basements after she and some peers expressed an interest in knowing the layout of the school. “I just remember how ecstatic our whole class was when Ms. Pelmas surprised us with this tour, and it honestly surpassed all my expectations. Her own excitement while leading us through ‘secret’ doors and mysterious passages made the whole experience all the more cool.”

Ms. Pelmas’s warmth and presence have undoubtedly made a lasting impact, and even played a role in some significant decisions. Winsor Trustee Wendy Cromwell P’21 recounts how her daughter, Caroline ’21, applied to co-ed schools as a Class IV student, but “ultimately decided to stay at Winsor—largely due to Sarah Pelmas.”

“Caroline loved Sarah’s warmth and intellect,” she continues. “She loved how Sarah knew everyone’s name and stopped to talk to them in the hallway. She loved how Sarah ended each assembly with ‘I love you guys.’”

Cromwell shares a story about one senior prank day, when the seniors hired a saxophonist to follow Ms. Pelmas around the school playing “Careless Whisper.” “Sarah took it all in stride,” she says. “I think this is what has impressed Caroline and me the most, that a woman of such intellect and accomplishment could also be so lighthearted and warm.” While her imprint will be lasting—from strong hires to navigating COVID to a focus on wellness and college counseling—“she is leaving Winsor a better place. But what she will be most known for, what her legacy will be, is leaving Winsor warmer.”

For Armine Afeyan ’08, Ms. Pelmas’s openness and warmth made a lasting impression for her and her sisters [Taleen Afeyan ’10 and Lena Afeyan ’13]. “I was struck by how easy and open our conversation was. Sarah was enthusiastic about getting to know us for the sake of knowing us, not just as Winsor alumnae but as people beyond that.” In fact, that conversation coupled with the retirement of their crew coach Lisa Stone, prompted the women to endow the Lisa Stone Chair for Crew. “As I’ve gotten to know Sarah over the years, I’ve remembered that conversation for the tone it set for all our subsequent interactions,” Armine says.

A Connector of Community

It’s no coincidence that Ms. Pelmas’s outgoingness and enthusiasm for Winsor laid the foundation for her strides in building community. Leading by example, she has served as a connector. President of the Winsor Board of Trustees Allison Kaneb Pellegrino ’89, P’21, ’22 was part of the search committee who initially brought Ms. Pelmas to campus. She shares, “The students and the faculty have always been at the heart of Sarah’s work at Winsor. In addition to Sarah’s intellect and deep understanding of and experience with adolescents were also her warmth and good humor. The search committee established to find Winsor’s eighth head of school was drawn to Sarah Pelmas by these qualities, and it was our hope that she would deepen the connectivity and relationships within the Winsor community. Sarah did exactly that when she arrived at Winsor.”

Kate Drachman ’25 points to Ms. Pelmas’s knack for using personal anecdotes and reflections to share meaningful messages. “Ms. Pelmas’s stories and their messages always leave me thinking about ways I can be a better friend, student, and community member.

In many ways, Ms. Pelmas has helped to foster the supportive and kind Winsor community that we share and cherish today.”

Julian Braxton notes that “Sarah deeply understands that community building and fostering a sense of belonging are critical aspects of her role. This perspective has made her an extraordinarily effective leader at Winsor. Our partnership has ensured that this important work is not siloed at Winsor but remains central to the school’s mission. Sarah consistently prioritizes community and inclusion, keeping these principles at the forefront of her leadership.”

He continues, “Leading together has truly defined our journey, and I am grateful for the partnership and legacy we have built together.”

Ms. Pelmas’s “presence and engagement with the community” has left a lasting impression on Julia Bae ’25. “Seeing her [at Winsor activities and events] showed her true, deep support and enthusiasm for the Winsor community.”

Likewise, Sherren Granese, Winsor’s director of athletics, has appreciated Ms. Pelmas’s enthusiasm for Winsor athletics. “She has a deep understanding of what it is like to be a student athlete and to represent Winsor on and off the field. …The students know and love when she is in the stands cheering them on.”

Ms. Pelmas was instrumental in bringing back the long-held tradition of inter-school squads—or inter-class sports competitions—that date back as far as 1915 but paused in the 1980s and 1990s with the rise of inter-school sports and a broader thrust for school-wide spirit. During the 2021–22 school year, Ms. Pelmas worked closely with SASS (Students Advocating for School Spirit) to re-launch inter-school squads, and “Panthers” and “Jaguars” have since competed in a host of games for the “house cup.”

Ms. Pelmas’s penchant for community building has extended beyond Winsor. Under her leadership, alumnae engagement has not only blossomed, but grown significantly beyond its historically Boston base with the launch of a “Beyond Boston” tour in 2023 and the expansion of rich online programming for alumnae. Notably, Winsor Alumnae Board Chair Ashley Marlenga Herbst ’01 lives in Dallas, Texas (see page 45).

Elizabeth Samet ’87 notes that Ms. Pelmas has a “wonderful facility for making alumnae feel closely connected to the school, no matter where they live.” She says, “Whether it be in the context of out-of-town alumnae gatherings, events at the school, or personal communications, she always conveys great warmth and enthusiasm.”

As Ms. Pelmas is honored and celebrated for her leadership and contributions to Winsor, her legacy will be woven into the fabric of those who led before her. In a blog post about the 2024 graduation, Ms. Pelmas aptly observed: “And as we celebrate, we also say goodbye, knowing that these goodbyes are not the end, but rather a part of the ongoing story of Winsor and its community.”

And like the women in portraits in the Virginia Wing Library that Ms. Pelmas has reflected upon, she will serve as a beacon to the women who will follow her. Kate Baker-Carr ’80 notes that Ms. Pelmas has shown a “deep knowledge of and admiration for each of her seven predecessors; she understood and deeply valued the unique contributions each head of school made—and continues to make—to Winsor. To be sure, the legacies are formidable. As Sarah prepares to join the small group of courageous, insightful, and wise women who have served as Winsor’s head, it is fitting to celebrate her unique contributions. Her legacy—like that of her predecessors—will be one of strength and vision.”