YEARS IN BUSINESS

Years

LOCATED IN

Massachusetts

NUMBER OF EMPLOYEES

Employees

NUMBER OF BOARDING SCHOOLS WE SERVE

Schools

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.

WHY BOARDING SCHOOLS CHOOSE US

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.

OUR MISSION

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