After a thoughtful search process that began in October and culminated Wednesday evening, the Orleans Central Supervisory Union board is pleased to announce that Jacquelyn Ramsay-Tolman has accepted the position as OCSU’s Superintendent, effective on July 1 with Penny Chamberlin’s retirement.
Jackie was one of three finalists selected by an interview committee created by the board. During the process of interviews, rigorous reference checks, forums for staff, faculty, and the public, student panels as well as visits to our schools, the board then participated in final interviews along with the interview committee. The board then voted to offer the position.
Ramsay-Tolman, is a dedicated and nationally networked education leader with over 25 years of progressive experience in teaching, and both school based and district-level administration. Her career spans roles such as Acting Superintendent, Director of Learning and Instructional Impact, Special Educator (Pre-K - 12th grade), and Principal, where she has consistently driven systemic improvements in student learning. Jackie is passionate about creating and sustaining systems that ensure every student—regardless of background or ability—has the tools and opportunities to thrive. She also serves as an adjunct professor at Saint Michael’s College, mentors future educators and leaders, and is a Nationally Certified Education Consultant, supporting schools nationwide in achieving improved outcomes through professional learning communities.
Rooted in a philosophy and deep belief in servant leadership, Jackie fosters trust, transparency, and innovation in all aspects of her work. Her expertise includes curriculum and assessment development, equity practices, social-emotional learning, and educational finance, supported by advanced certifications from institutions like Georgetown University and the University of Washington. A Vermont-based leader with deep ties to rural communities, Jackie’s work reflects her commitment to building inclusive systems that address and honor the unique needs of each learner. Her ability to develop authentic relationships with students, educators, families, community, and policymakers has established her as a respected leader and advocate for public education.