Wilderness Trip Leader

About the role

Stevenson School is a PK-12 co-educational, college-preparatory, boarding and day school with approximately 750 students on two campuses in Central Coast California. The Upper Division (Grades 9-12) is in Pebble Beach; the Lower/Middle Campus (Grades PK-8) is in Carmel-by-the-Sea. The school’s mission is to help students shape joyful lives while instilling a passion for learning and achievement. Core values are safety, trust, respect, belonging, and inclusion. Outdoor Education is a signature program, highlighted by an expedition series that provides personal growth opportunities.

Stevenson is seeking Trip Leaders for the Sophomore Wilderness Expedition, a 10-day backpacking course taking 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, with a front-country manager providing logistical and emergency support. This is a temporary, seasonal position. Ideal candidates 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, candidates should demonstrate a commitment to equity and inclusion; candidates from underrepresented backgrounds are encouraged to apply.

Responsibilities

• 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

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 submission of a receipt to the HR Office