About Jackie

Jackie O’Rourke established Outermost Education Services in 2018 after several years of wondering how she could use her experiences as a former boarding school student and educator to assist schools on their path to excellence. By extending her love of teaching to include educator training, program review and development, and personalized mentoring, Jackie hopes to play a role at schools across the country as they seek to improve the experience of their students.

I was raised on Cape Cod and spent four years at Cushing Academy in central Massachusetts. As a student, I learned a great deal about the inner-working of boarding school life through my experiences as an admission tour guide, a three-season member of varsity athletic teams, and as a dorm proctor. I loved campus life from the start and knew long before graduation that I would return to boarding school after college to live the life of the teacher, coach, and dorm parent.

As a boarding school faculty member, I’ve served in many roles, though the Student Life and Residential components have always held a special place in my work. From dorm parent and dorm head, to Activities Director and Dean of Residential Life and Leadership, my experiences have challenged me to be a dynamic observer of how our policies, programs, and routines impact the daily lives of our students. I love the connections forged in boarding school, whether in my English classroom, on the field or rink, or over late night snacks in the dorm, kids come first in boarding school. In my role as a consultant, the students we serve remain at the forefront as we work collaboratively to be at our best for the many students whose lives we will impact together.

While attending Williams College I met another “boarding school lifer” from Berkshire School in Massachusetts, and together we have lived and worked at boarding schools in Massachusetts, New Hampshire, and Madaba, Jordan. We each earned our Masters degrees from Boston University to further develop our skills as educators.

We’re a family-owned firm with a community-first approach. Get in touch to start your journey with Outermost Education today.

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About Maureen

Maureen Harrison joined Outermost Education Services in 2022. With years of experience and knowledge of boarding school culture, Maureen partners with Jackie to offer training opportunities for Student Leaders and their mentors.

Raised south of Boston in Marshfield, MA, I first became aware of the boarding school world as a student at Williams College.  While sharing a “Science on the Road” lesson with nearby schools, my eyes were opened to the possibilities of boarding life - the diverse community, the myriad opportunities, the relationships beyond the classroom; I was hooked.  After a brief stint as a neuroscience researcher (think rats in mazes), I joined the faculty of Emma Willard School in Troy, NY.  For the next 27 years, I embraced campus life as I lived in the dorms, scored basketball and volleyball games, taught chemistry and neuroscience (primarily), served as the Learning Support Coordinator, advised countless students, and mentored the senior proctors and other student leaders, earning an MS in Curriculum Design from SUNY Albany along the way.


As a lifelong Girl Scout, my summers were often spent at residential camps.  As a camp director, I expanded my toolbox of noncompetitive games and teambuilding initiatives.  I also honed my skills around group formation and reflective conversations through trainings with Project Adventure.  Focusing on relationship building, these techniques and activities form the backbone of my interactive work with students and with the adults who mentor them.


My partner and I (and our cat, Mia) have recently retired from Emma Willard to move to the Adirondack Mountains of NY.  We loved the energy of living with teenagers and we also love the quiet of the woods.  And now, I am looking forward to the opportunity to explore leadership mentoring more fully through my collaboration with Jackie and Outermost Education!

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