Kevin Driscoll joined Vermont Academy on August 1, 2025, following several years in higher ed advancement, working as a Major Gifts Officer in Tufts University Advancement assigned to the Tufts University School of Dental Medicine in Boston. Passionate about independent schools, with a special love for small boarding schools and their important place in the independent school realm, Kevin felt the call to return to boarding school work, and at the same time also makes a return to Vermont, a state he calls his true north and second home. A graduate of Saint Michael’s College in Colchester, Kevin is not unfamiliar with Vermont, having also spent childhood summer vacations in Saint Albans with family on the shores of Lake Champlain, he is thrilled to return to the Green Mountain State.
Kevin’s independent boarding school experience began soon after college graduation at Eagle HIll School in Hardwick, MA, where he served as the school’s Weekend Duty Master. He fell in love quickly with life on a small boarding school campus. He then moved on to join the faculty at Phillips Academy Andover, (his hometown), which was followed by stints as a Dean of Students at the Dublin School, NH, Director of Young Alumni and Giving at Governor’s Academy (MA), Director of Admission at Austin Prep, a Catholic independent day school outside of Boston, and then a return to a small boarding school, High Mowing School in Wilton, NH, America’s oldest Waldorf boarding school, before transitioning to higher ed work at Cambridge College and Tufts University.
Kevin brings significant experience in external relations, including advancement, admissions, and institutional strategy. He has participated in successful capital campaigns, enrollment initiatives, and development efforts while also designing rebrands for two of his previous schools and assisting in the development of strategic plans, campaign initiatives, and creating new innovative ways to connect with alumni, near and far. He is a collaborator, and visionary in his leadership, and also draws on his sense of humor, that lead to a brief but exciting career in stand up comedy in his years just after graduating from college.
Kevin brings to VA a much needed capital campaign background, having helped lead campaigns at Austin Preparatory School, where he helped with two campaigns, the larger of the two saw the transformation of the former vacant St Augustine Hall Monastery into a robust and life filled classroom, performance, visual and media arts center. At High Mowing School he worked alongside his colleagues in Development to help secure the former Frye Farm, to serve as a conservation area for the campus, and secure the magnificent views and peacefulness of the campus hilltop for generations to come. In his most recent work at Tufts University School of Dental Medicine, Kevin had a principal gift portfolio of 100 high level donors, and was involved in the successful completion of Tufts 1.5 billion dollar, Brighter World Campaign. Kevin was responsible for donor relations and major giving programs on the West Coast, Florida, and the Northern New England States. He was responsible for the creation of several endowed scholarships during his years at Tufts, and was also the primary connector to the Northeast Delta Dental Tufts Summer Interns Program which he helped develop at Tufts Dental to match dentists in northern New England with current students at Tufts Dental, where these students would spend 3-4 weeks in the summer observing dentistry operations. The goal was to introduce the possibility of living and serving in these rural northern New England regions after graduating as dentists.
Kevin earned his B.A. in American Studies at Saint Michael’s College and his M.Ed. in Multi-disciplinary School Leadership at Cambridge College.
Kevin has three adult daughters, Mackenzie, Grace, and Addison. He lives on campus in Wolcott House with his trusted canine companion Phoebe (he and his daughters are avid “Friends” aficionados), a rescue dog from Mississippi. He is excited to be back in the Green Mountain State and back on a boarding school campus. He is already engaging in meetings with alumni and friends of VA, and is excited to continue meeting constituents on campus and on the road to raise awareness and build support for this amazing school!