By Sophia Lichterfeld

“Every Day. For Everyone. Together.” These are the words printed at the top of Winsor’s current Strategic Mission, a document that the school creates every five to ten years with 20 to 30 objectives for the community to work toward. It is the responsibility of the Board of Trustees to guide the efforts aimed at achieving these goals. How does the Board work to reach these targets, and what specific steps is it focusing on in the next few years?

According to the President of the Board of Trustees Mrs. Allison Pellegrino ’89, P’21, ’22, the 28-member group meets five to six times each year. In addition, subcommittees of the Board meet three to six times each year. The subcommittees include the Advancement Committee, Audit and Risk Committee, Finance Committee, and Investment Committee which work on managing Winsor’s fiscal responsibilities and endowment; the Heads’ Compensation and Evaluation Committee; the Committee on Trustees which reviews the Board’s work and proposes new trustees; the Facilities Committee that focuses on property and development projects in the area; and the Equity Committee, that encourages DEI work both at Winsor and specifically on the Board) within the Board meet regularly as well. Board meetings are reserved mainly for discussions and updates from subcommittees. However, while the Board makes recommendations for courses of action, the “governing body” of the school, as Mrs. Pellegrino referred to it, is actually the Winsor School Corporation. The Corporation consists of 200 members of the Winsor community, including graduates, past trustees, parents, and all current trustees. The Corporation must approve incoming trustees, the hiring of the Head of School, and any major fiscal decisions. 

Furthermore, at Winsor, the Head of School plays an integral role on the Board. Ms. Pelmas estimated that 30% of her time is devoted to the Board’s initiatives. She participates in all subcommittee meetings, of which there are about 35 to 40, annually. Ms. Pelmas said that she “help[s] plan the agenda so that we can make sure the Board is informed about the most pressing issues facing the school.” Mrs. Pellegrino noted that “Ms. Pelmas gives us insight into faculty and student voices at Board meetings, as do other administrators and faculty members that come to speak to the Board.” Associate Head of School Ms. Caspar, Director of Advancement Ms. McMahon, Director of Admissions Ms. McFarland, and Chief Operating Officer Ms. Geromini are invited to all Board meetings. Students and faculty are also welcomed to Board meetings to give presentations. “Honestly, if students or faculty wanted to present to the board they can speak with Ms. Pelmas or contact me directly. We’d love to hear from students!” Mrs. Pellegrino said. She mentioned that, for example, the project of installing solar panels on the roof of the LOC last year was proposed by a group of students, and she recalled that the Student Equity Board had also spoken at Board meetings. Wellness Department Head Ms. Santos Valenzuela also recently presented to the Board.

Mrs. Pellegrino stated that “our primary goal as a Board is to ensure that the mission of the Winsor School is upheld.” In recent years, the Board’s priorities have been focused on organizing a capital campaign. Specifically, after the previous fundraiser that raised 82 million dollars—more than double any campaign in the past had—toward building the LOC, the Board is now working toward the largest fundraising initiative in the school’s history, intended to benefit faculty salaries and make Winsor more financially accessible. Mrs. Pellegrino remarked that “it’s easy to make a case for contributing to Winsor because I am able to say [from my experiences] that it is essential that students have an education like this.” 

The Board has also been working on campus master planning and discussing how to best use the facilities available. They have been making sure that Winsor’s needs are considered in a construction project that will occur on the left side of Pilgrim Road; Mrs. Pellegrino said, “It might seem kind of boring, but it’s really important to make sure our little seven-acre campus is protected.” Moreover, Ms. Pelmas commented that the Board was arranging funds to invest toward building facilities Winsor might need in the future.

Finally, one of the Board’s focuses for this year is promoting DEI and wellness at Winsor. Aiding DEI work is particularly addressed with the Equity Committee and is emphasized when the Board considers how to distribute its funds for the year. Relating to wellness, Ms. Pelmas explained that “the main way the Board supports wellness is through the budget priorities: approving the funding of two counselors and a teaching and learning specialist, as well as approving the creation of the Wellness Department and the funding for its programs.”

Overall, the Board’s main objectives are to protect the school’s financial interests, to support action toward wellbeing and DEI, to assist the Head of School, and to communicate with the broader Winsor community. Finally, Ms. Pelmas shared, “I really love working with the trustees because they are so passionate about Winsor and they never settle for less than the very best for the school. They push me to do my best work as the Head of School, and they are always so very proud of the students and teachers here.”