Historic New England Boarding School Marks Strategic Milestone with Senior Leadership Appointment
Cheshire Academy is proud to announce the appointment of Melissa T. Terrio, M.Ed., as its inaugural dean of enrollment management, effective May 1, 2026. This newly created senior leadership position represents a defining moment in the school’s evolution.
Founded in 1794, Cheshire Academy has long stood as a leader in global, internationally minded education. As one of the oldest boarding schools in the U.S., the Academy enters an exciting new phase of strategic planning under Head of School Tom Woelper P’26. The creation of a dedicated enrollment management function signals the school’s commitment to sustainable growth, intentional brand building, and a student experience that begins long before a student ever sets foot on campus.
“I am thrilled to be joining Cheshire Academy as the inaugural dean of enrollment management,” Terrio said. “Throughout my time on campus, I was struck by the strength of the Cheshire community — its warmth, diversity, and genuine sense of welcome — as well as the beauty of the campus itself. It is clear that Cheshire Academy offers a distinctive environment where students are known, supported, and encouraged to thrive across social, athletic, artistic, and academic dimensions.”
A Transformative Addition to the Leadership Team
Terrio brings more than 25 years of distinguished leadership in enrollment management, admissions, and marketing to Cheshire Academy. Most recently, she served as assistant dean of graduate and professional Studies at Worcester Polytechnic Institute (WPI) in Worcester, MA, overseeing a team of 30+ staff across graduate admissions, marketing, recruiting, and student success functions. In her role as executive director of graduate studies at WPI, she drove a remarkable 30% growth in BS/MS enrollment over five years — a result of disciplined strategy, data-informed decision-making, and exceptional team leadership.
Her career spans some of the most respected institutions in higher education, including HEC Paris MBA in France — where she lived and worked, developing the global fluency that informs her approach to international recruitment to this day. She is currently pursuing a Doctor of Education in Higher Education Administration at Northeastern University, where she also earned a Master of Education in Higher Education Administration.
Woelper expressed his enthusiasm for Terrio joining the Cheshire Academy leadership team: “Melissa’s appointment is an extraordinary step forward for Cheshire Academy. Her experience in enrollment leadership, from strategic planning and data analytics to international recruitment and team building, is exactly what this school needs as we lean into our strategic planning process and look to the future.”
Global Perspective, Independent School DNA
Terrio has lived and worked in Australia and France, traveled extensively across more than 40 countries for professional recruitment purposes, and has served as a Designated School Official (DSO) for SEVIS — giving her a command of international student visa regulations and the nuanced needs of global families navigating the U.S. independent school admissions landscape. In a school where students hail from 18 countries and 13 states, and a mission that centers on developing purposeful global citizens, this expertise is essential.
That global sensibility is grounded in something equally important: Terrio knows independent school life from the inside. As a student at Cushing Academy, she experienced firsthand the transformative power of a boarding school education — the community, the challenge, and the sense of belonging that shapes a student for life. That lived understanding, combined with her breadth of professional expertise, means she comes to Cheshire Academy not just as a skilled enrollment strategist, but as a genuine advocate for the independent school experience she is helping families discover.
Building the Future of Enrollment at Cheshire Academy
The Dean of Enrollment Management position is a purposeful creation, born from the recognition that sustainable enrollment requires integrated strategy, robust data systems, a cohesive brand presence, and deep alignment between how the school presents itself to the world and the experience it delivers. Terrio is uniquely positioned for this function.
The school extends its sincere gratitude to DovetailED as well as the internal Dean of Enrollment Management Search Committee, whose guidance ensured the school identified not only a highly qualified professional, but the right leader for this pivotal moment in Cheshire Academy’s history.
“I look forward to working with the talented Admission Office in telling the Cheshire story in a way that authentically reflects its values and introduces families to the richness of the student experience. I see tremendous opportunity for relationship building and collaboration across the team at Cheshire Academy, grounded in a shared commitment to student success and community.”
