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.


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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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