Welcome to our New Dean of Student Life Kelly O'Ryan

Kelly is an educator, administrator, and restorative practices leader with nearly twenty years of experience supporting students and building inclusive learning communities. Currently serving as a local principal, Kelly is recognized for her student-centered leadership, commitment to belonging, and ability to cultivate environments where young people can thrive academically, socially, and personally.

Kelly has held leadership roles in both secondary and higher education, including senior administrative positions at Landmark College and Greenwood School. Her work has focused on student development, restorative justice, equity and inclusion, crisis response, and supporting neurodiverse learners. A passionate advocate for experiential education, she has also facilitated international youth leadership and peacebuilding programs throughout the United States, Europe, and the Middle East.

Throughout the interview process, colleagues were struck by Kelly's calm presence, thoughtful leadership, and deep commitment to students. Search committee members repeatedly noted her ability to make difficult decisions while communicating with care, as well as her expertise in restorative practices and student development. Students appreciated how carefully she listened and how her questions helped conversations evolve into bigger ideas about advisory, belonging, and community life. Others highlighted her ability to bring greater structure, accountability, and consistency to student life while maintaining a deeply relational approach. Several committee members remarked that Kelly possesses the rare ability to be both unflappable and empathetic. She is a leader capable of supporting students through challenges while helping a community move proactively toward its aspirations.

"Kelly understands that belonging and accountability are not competing values; they are mutually reinforcing," said Head of School Mike Peller. "She brings a rare combination of warmth, wisdom, and courage to this work. She understands that great student life is not built through rules alone, but through relationships, trust, and shared purpose. Kelly has devoted her career to helping young people discover who they are, find their place in a community, and develop the skills to lead meaningful lives. Her experience, empathy, and vision make her precisely the leader Vermont Academy needs in this moment."

Kelly earned her B.A. in Global Studies from St. Lawrence University and her master's degree from the School for International Training. She is currently completing her doctorate in Educational Leadership through New England College.

Outside of her professional work, Kelly enjoys spending time with her family skiing, camping, and supporting her children at regional freeride competitions and local theater productions. She and her husband, Sergio, have three children and reside in Putney, Vermont.

Vermont Academy looks forward to welcoming Kelly and her family to campus and to the leadership, care, and sense of purpose she will bring to the student life of the school at this exciting moment in its history.