Middle School/Upper School Outdoor Biking Trip Leader

About the Role:

Lakeside School, an independent coeducational day school located in north Seattle, Washington, is currently recruiting for an outdoor biking trip leader to lead trips for 7th grade students in May 2026 and high school students in August 2026.

Lakeside Middle School’s Outdoor Program consists of 4-day, 3-night backpacking trips for 7th grade students, and 3-day, 2-night camping trips for 6th grade students. Lakeside Upper School’s outdoor program consists of a 6-day, 5-night wilderness experience across a variety of different activities. The goals for the program are to help students:

• Develop a sense of place in the Pacific Northwest:

• Learn how to contribute as members of teams;

• Practice problem solving;

• Take physical, emotional, and social risks;

• Learn the fundamentals of ‘wilderness’ backpacking and camping and leave no trace protocols.

Responsibilities

The outdoor biking trip leader is one of two or three adults to co-lead, co-manage, and execute all aspects of the trip for a group of nine to eleven students. Core responsibilities include but are not limited to:

• Supporting student learning by facilitating group activities with a diverse group of students.

• Supporting a diverse student body who will come into the program with a wide array of outdoors experience, including many students with limited or no outdoor experience.

• Providing wilderness, camping, and biking expertise as well as teaching students relevant and appropriate skills and knowledge in these areas.

• Managing risk appropriately to create a safe and supportive environment for all students.

• Driving students to and from site and as needed during the trip, most likely on a minibus pulling a trailer (training provided).

• Provide bicycle repair and maintenance on trips for students as needed, including fixing flats, broken chains, and other common issues.

The trips are planned as follows:

• Leader training day – Monday May 11, 2026

• 7th grade prep day – Monday May 18, 2026

• 7th grade biking trip – Tuesday May 19 – Friday May 22, 2026

AND

• Olympic Biking trip prep day – Saturday August 15, 2026

• Olympic Biking trip (high school) – Sunday August 16 – 21, 2026

For interested leaders, there is also an opportunity to work 6th grade camping trips on the following days:

• 6th grade prep day – Tuesday May 12, 2026

• 6th grade camping trip – Wednesday May 13 – Friday May 15, 2026

• Leaders must be available for the leader training day, the prep days and all days of the trip in which they are leading. Training and prep day hours will be approximately 8:00am – 4:00pm at Lakeside School in Seattle. Most trips will plan to depart around 8am on departure day and return by 4pm on return day, though some hours may vary depending on the trip. Leaders may need to stay later than 4pm to clean up after the trip on trip return days.

Successful candidates should:

• Be at least 21 years of age;

• Have experience leading multi-day wilderness expeditions working with middle school age children;

• Have experience working with diverse student populations and demonstrated equity and inclusion mindset. Candidates should be aware of their own identity and biases, consider how privilege impacts outdoor recreation spaces, and take into account student’s varied exposure to the outdoors.

• Have experience and willingness to contribute to all group activities;

• Have training and/or experience in experiential/outdoor education;

• Have experience doing bicycle maintenance and adjustments;

• Have experience leading bicycle tours or other biking based trips or activities;

• Demonstrated cultural awareness, including knowledge of themselves and the cultural lenses they bring to interactions. The candidate will understand different perspectives; interact respectfully with cultures other than their own; and cultivate meaningful relationships with people that have different cultural frameworks.

• Must possess current Wilderness First Aid & CPR certifications at a minimum, though Wilderness First Responder is strongly preferred.

• Willingness to be trained in and able to drive a mini-bus (15 passengers) preferred, but not required. (No special license required, drivers must be 25 years old.)

References should speak to the applicant’s integrity, flexibility, and ability to be an effective member of a team. Additionally, candidates must satisfactorily complete two criminal background checks

Compensation

Outdoor trip leaders will be paid $200/day for each of the training and prep days. For all trip days, leaders will be paid between $260 - $300/day depending on their skills and experience.

Application Process

Interested candidates should submit a brief cover letter, resume, and work history. Applications will be accepted until the position is filled. Lakeside School is an equal opportunity employer seeking to diversify its workplace.

Working At Lakeside

At Lakeside we are committed to sustaining a school in which individuals representing diverse cultures and experiences instruct one another in the meaning and value of community. To learn more about working at Lakeside, including our professional development and mentoring programs, benefits, diversity and inclusion, and opportunities for involvement in non-academic programs, please visit our Careers page on the Lakeside School website.

Participate in the 2026 Diversity Career Fair hosted by POCIS Northwest

Virtual: Sunday, February 8, 2026, 9am-12pm PST on Zoom

In-Person: Saturday, February 28, 2026, 9am-12pm at The Lakeside Middle School

For more information and to register, visit Diversity Career Fair