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| Company Name: |
Midland School |
| Location: |
Los Olivos, CA United States |
| Position Type: |
Full Time |
| Post Date: |
05/28/2026 |
| Expire Date: |
07/28/2026 |
| Job Categories: |
Education |
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Outdoor & Student Life Assistant
Boarding school setting
Grades 9 to 12 students
Full-time/academic year role
On-campus housing* & meals
Salary range $38K-45K, commensurate with experience*
Position starts August 2026
Primary Duties & Responsibilities:
Support delivery of outdoor program (current programming includes: backpacking, rock climbing, mountain biking, surfing and trailwork)
Lead overnight backpacking trips & teach wilderness skills/leadership to high school students
Work with the Dean of Residential Life in supporting all aspects of student life at Midland including student supervision, offering student clubs, supporting affinity groups, & off-campus outings.
Assist with driving and student transportation for health office & sports/activity programs
Day-to-day residential community engagement & participation in all school-wide events
Qualifications & Requirements
Minimum Qualifications:
Wilderness First Aid or higher (Wilderness First Responder preferred)
Experience working in outdoor education (particularly backpacking, mountain biking, and/or rock climbing).
Hard working in a physically demanding position
Enthusiasm to work with teenagers in a residential setting
Excellent communication skills
Ability to work as a team and collaborate with others
Possess a positive attitude, have high energy and be self-directed
Successful passing of criminal background & driving checks
Health clearance for TB screening
Additional Desired Experience:
AMGA SPI rock climbing certification (or higher)
Significant personal and professional (e.g. guide/instructing) experience in any of the following areas: backpacking, rock climbing, mountain biking, and/or surfing.
Experience working with adolescents especially in boarding or residential education environments
Other skills and interests to share with our community - coaching athletics & activities, elective classes, performing arts (please share specifics via cover letter)
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| Contact Name: | Karrie Glines |
| Company Name: |
Midland School |
| Contact Email: | kglines@midland-school.org |
| Website: | https://midland-school.org/join-the-team/ |
Company Description:
Midland School, a distinctive co-educational boarding school for grades 9-12, is located on a 2,860-acre ranch at the edge of the Los Padres National Forest. Midland has been a leader of place-based and experiential college preparatory education since 1932. Everything we do—from the courses we choose to teach, to how we maintain our campus, to the way we feed ourselves— originates from an intentional curriculum that focuses not only on academics, but also on leadership, community, and stewardship. Our students live a cell-phone-free high school experience, close to nature.
Our campus residential community is filled with outdoor enthusiasts, farmers, animal lovers, artists and, of course, friendly and talented faculty and staff. If you would like to be a part of a team dedicated to teaching the value of a lifetime of learning, self-reliance, simplicity and a responsibility to community, we invite you to apply.
This position is open until filled. The start date is mid-August 2026.
Applicants should first carefully review the minimum qualifications and the Midland School website to learn more about our school. If interested, submit the following as a single PDF file titled "lastname_firstname_OSLA_2026" to Karrie Glines, Assistant to the Head of School, at kglines@midland-school.org. Only complete applications will be considered.
Short cover letter that addresses the alignment of your experience and interests with the qualifications outlined above and Midland School’s mission
Current resume
List of 3-5 references
Midland School is an equal opportunity employer and actively seeks diversity among our employees.
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