Wilderness Trip Leader

Stevenson School; Pebble Beach (CA); On-site; USD 35,000 - 46,000; Part time

Benefits offered by this job

Meals provided

Paid staff training

LiveScan reimbursement

Job summary

Stevenson School is seeking Trip Leaders for its Sophomore Wilderness Expedition, a 10-day backcountry adventure February 26 – March 7, 2027 in Henry Coe State Park. Coed crews of 9–11 students travel with outdoor educators and student leaders, guided by a front-country manager for logistics and safety.

Ideal candidates bring strong wilderness leadership with experience supervising teens and a passion for growth through outdoor adventure.

Qualifications

• Outdoor leadership training required.
• Proven experience leading extended backcountry trips with high school students.

Responsibilities

• Lead in co-instruction with another staff member.
• Attend mandatory training February 4–7, 2027.
• Lead expedition preparation February 25, 2027.
• Oversee wilderness expedition Feb 26–Mar 7, 2027 and debrief Mar 8, 2027.
• Maintain safety protocols and support in emergencies.
• Foster an inclusive environment among participants.

Skills

Outdoor leadership

Teen leadership

Job description

Stevenson School is a PK-12 co-educational, college-preparatory, boarding and day school with enrollment of approximately 750 students on two campuses in beautiful Central Coast California The Upper Division campus (Grades 9-12) is located in Pebble Beach. The Lower/Middle Campus (Grades PK-8) is in nearby Carmel-by-the-Sea. Stevenson is a mission driven school that aims to help students shape joyful lives while instilling a passion for learning and achievement to prepare them for success in school and beyond. The core values of the community are safety, trust, respect, belonging, and inclusion.

Highlighted by an expedition series that provides personal growth opportunities for students, Outdoor Education is a signature component of Stevenson’s educational program.

Stevenson School is seeking Trip Leaders for our Sophomore Wilderness Expedition, a 10-day backpacking course that will take place February 26 - March 7, 2027 in Henry Coe State Park. Coed crews of 9-11 students are accompanied by outdoor educators and student leaders. A front-country manager provides logistical and emergency assistance.

This is a temporary, seasonal position Ideal candidates will possess strong wilderness leadership skills, experience working with teenagers, and a passion for fostering growth through outdoor adventure.

In keeping with Stevenson’s core values, we seek candidates who demonstrate a commitment to equity and inclusion. Candidates from underrepresented backgrounds are encouraged to apply.

Compensation and Logistics

• Pay: $220 per day
• Meals: Provided during training and the expedition
• Training: Mandatory paid staff training February 4–7, 2027 plus a half day final preparation on February 25 and a breakdown day on March 8
• Background Check: LiveScan required, to be reimbursed upon a submission of a receipt to the HR Office

Responsibilities Include:

• Participate in co-leader instruction
• Participate in paid staff training weekend trip, February 4-7, 2027
• Participate in a half day of final preparation before the expedition, February 25, 2027
• Participate in the Sophomore Wilderness Expedition, February 26 - March 7, 2027 and debrief on March 8, 2027
• Share technical expertise and group skills with the instructor group
• Lead formal and informal instruction on topics appropriate to wilderness travel and living
• Actively communicate, engage in, and enforce safety protocols
• Provide appropriate support in emergency and/or medical situations
• Actively participate in the creation and maintenance of an inclusive environment

Required Qualifications:

• Outdoor leadership training
• Demonstrated prior experience successfully leading extended backcountry trips with high school students

Preferred Qualifications:

• Wilderness First Responder (WFR) level medical training

Stevenson is an equal opportunity employer and does not discriminate on the basis of race, color, religion, sex, gender identity, national origin, age, disability, marital status, sexual orientation, or any other characteristic protected by law.