Outermost Education Services

Comprehensive independent advising for boarding schools, offering program assessments and design, custom training sessions for faculty, and professional coaching for educators and parents.


Schools are constantly growing to meet the needs of our students. Rather than relying on a prepackaged approach, we seek to collaborate with educators throughout the process to provide a unique service as needed for each of our schools. We set out to cultivate an understanding of your school’s history, mission, and vision for the future before establishing a plan to generate engaging training sessions, inspiring mentoring experiences, and in-depth audits.


Honoring the values of honesty, love, trust, and empathy, Outermost Education Services seeks to bring schools closer to realizing their own missions for student and community success.
Jackie understands the complexities of boarding schools and the many facets of this unique educational opportunity. While possessing this wealth of knowledge, Jackie has a keen talent for connecting with people in a variety of settings.
Doug Dickson - Assistant Head of School for Student Life, Episcopal High School, VA
As a young teacher, fresh out of college, Jackie’s guidance and mentorship were invaluable in navigating the precarious nature of boarding school life. Her holistic approach towards identifying what was best for both the students and faculty fostered relationships that cultivated the school community, transforming the campus into a home.
Liam McMahon - Faculty member, Williston Northampton School, MA
Jackie O’Rourke brings both passion and vision to her work with schools and faculty members. She has been a boarding school student and member of the faculty, and those experiences have informed her own work in a variety of roles within boarding schools. She is clear sighted about school issues, and she is clear voiced in her appraisals. I have witnessed her work with people new to boarding schools, and she is wise, tough, and tender. I can’t think of anyone better to assess a situation and to provide clear counsel about moving toward a solution.
Jay Bonner - Assistant Head of School, Asheville School, NC
Jackie was a great support to me, as a mom of a student who was suddenly struck with some panic attacks and anxiety issues in the middle of his freshman year. She was kind and supportive of me, helped to communicate my worries and fears to the teachers, and she was instrumental in helping us navigate and manage some stressful times to a successful conclusion!
Angela Keef - P ‘20 Tilton School, NH


Will Gilyard is in his 19th year of working in independent schools. In 2020, he returned to his alma mater Choate Rosemary Hall to take on the roles of Form Dean, and Alumni Engagement Associate. Will joined Choate after nine years at the Kingswood Oxford School (KO), a 6-12 independent day school located in West Hartford, CT, where he served as Dean of Students, an upper school math teacher, assistant football coach, and faculty advisor for the United Students club and Boys of Color group. At Choate, Will is the faculty adviser to Choate Afro Latino Men (CALM), and Girls Who Code (GWC).

Will also serves as a core faculty member and helped create the curriculum for the Institute for New Teachers of Color in Independent Schools, created in 2020, the Interschool Leadership Institute, created in 2013. Will also served as a core faculty member of the Kingswood Oxford Leadership Institute for Educators of Color (KOLIEC) from 2011-2018 and helped create the curriculum for the mentoring/advising circles for institute participants.

Before joining KO, Will was the Head of the Upper School at the Cathedral School of St. John the Divine in New York City. He serves on the board of advisors for the IDEAL School, also located in New York City. He is passionate about the role of educators in independent schools, specifically in the lives of students of color. Will has attended numerous workshops, conferences, and institutes related to leadership in independent schools and anti-racist education. Will had the honor of being a member of a think tank for the CARLE institute. 

Will has his B.A. in Psychology from Williams College and his M.A. Ed. in Curriculum and Instruction from the University of St. Joseph. Will is thrilled to be a part of the TABS (The Association of Boarding Schools) team and looks forward to working with energized and focused individuals who are interested in being change agents in the residential life sphere.

Will and his wife, Afton, ALP/Enrichment Teacher in Stratford Public Schools reside in Wallingford, CT with their two sons, William (10) and Maxwell (8).


Associate Head of School Ryan Pagotto ’97 joined Blair’s faculty in 2002 and is responsible for managing the day-to-day operations of the School on matters related to student and residential life, including health and counseling services, athletics and co-curricular programs. He runs Monday School Meeting and, among other things, is known for greeting students in the morning at the Clinton Hall doorway and offering freshly picked apples from his office during the month of October. In addition to his administrative responsibilities, Ryan serves as a member of the history department and teaches Global Issues. He also authors the monthly e-newsletter From Hilltop to Home, a communication designed to help new boarding-school parents navigate the ins and outs of the Blair experience.

Over the course of his time at Blair, Ryan has served as a history teacher, head tennis coach, a dorm head and Dean of Admission. He completed his undergraduate work at Dickinson College, where he captained the men’s tennis team, and earned a master’s degree in educational leadership from Columbia University. Before joining the faculty at Blair, Ryan taught at the Taft Summer School in Watertown, Connecticut, and Wyoming Seminary in Kingston, Pennsylvania. He also spent three summers as program director of the Cambridge Prep Experience at Peterhouse College, Cambridge University.

In addition to his roles in schools, Ryan has served as a faculty member for the TABS (The Association of Boarding Schools) Summer Session and is a regular presenter at national boarding and independent school conferences on student and residential life.

Ryan and his wife, Jennifer, performing arts department chair and Director of Instrumental Music at Blair, live in Grullon House with their children, Jack, Will, Ella and Addison, and their dog, Teagan. The Pagottos enjoy opening their home to Blair students, faculty and staff members throughout the year.


Susan served as a professor and leader at Middlebury College for over 25 years, most recently as Executive Vice President and Provost, leading Middlebury’s academic programs across multiple campuses – Middlebury, Bread Loaf, Monterey – as well as study abroad locations around the world. Prior to her Provostship, Susan served as Vice President for Strategy and Planning, Dean of Planning and Assessment, and Dean of the Faculty. She is a tenured Professor of Psychology and taught throughout her time at Middlebury.

Susan began her consulting firm in 2018, advising schools, colleges, non-profits and foundations in the areas of strategy, planning and governance; and coaching senior administrators to build leadership capacity and support change management. This led her to partner with TABS in 2019, in the development of TABS current strategic plan.

In addition to consulting, Susan co-authored the book, The College Stress Test, an analysis of educational markets and tools for helping schools to identify their place within market trends. The book was named one of the best books on higher education in 2020 by Forbes Magazine. Susan has presented extensively on topics relating to human sexuality, social psychology, and the psychology of women and gender. She received her B.S. with highest honors in Psychology, Phi Beta Kappa, at Denison University, and her M.A. and Ph.D. in Social Psychology at UCLA.