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.

• 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

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)

Work at Midland! 

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.

About Midland School

Midland School provides a unique college preparatory boarding school experience to a diverse student body. Through study and work, it teaches the value of a lifetime of learning, self-reliance, simplicity, responsibility to community and the environment, and a love for the outdoors Founded in 1932 in the midst of the Great Depression, Midland has always been an “alternative to the regular thing.” Our founding mission and values have guided us through economic recessions, world wars, cultural shifts and, most recently, a global pandemic. Our focus remains steady: to provide a rustic college preparatory education to students of all backgrounds, to create lifelong thinkers and learners and to teach students to live simply and connect deeply with the natural world. Across Midland’s nine decades, much has changed. Every so often, our community reevaluates our shared values and mission to ensure they remain reflective of the school and community we desire to be. Today, these beliefs remain the strong foundation beneath our academic and residential program:

Connections working at Midland School