Seasonal Instructor (9 month)

Philadelphia Outward Bound School is seeking Seasonal Instructors to support expeditions, challenge course programs, and logistics. Instructors work a varied schedule that may include co-leading wilderness expeditions in Pennsylvania and New Jersey, facilitating challenge course experiences for youth and adults at our Philadelphia locations, and supporting expedition logistics. 

Seasonal Instructors receive comprehensive training that includes classroom sessions on Outward Bound history and philosophy, student management, conflict resolution, safety and risk management, diversity and inclusion, curriculum development, and more. Staff also receive technical training in backpacking, canoeing, top-rope and indoor rock climbing, and challenge course facilitation. 

About Us

Outward Bound is an international educational movement dedicated to the belief that people are capable of far more than they know. Founded in 1992, Philadelphia Outward Bound School's (POBS) mission is to change lives through challenge and discovery. POBS – serving PA, NJ, and northern DE – is one of 9 regional Outward Bound USA schools. A robust, non-profit educational organization, POBS annually engages more than 7,000 youth and adult participants in single and multi-day experiential education programs that inspire character development, leadership, and community service. All programs are designed to inspire participants to realize their true potential.

Position Responsibilities 

Instructor Responsibilities

• Plan and co-lead multiday wilderness backpacking, rock climbing and/or canoeing expeditions (5 – 14 days in length)
• Assist with course preparation & debriefing – including backpacking & canoeing equipment preparation, cleaning & repair; food packing; vehicle and trailer loading; and participant transportation.
• Facilitate group discussions, reflection activities, and lessons that promote Outward Bound values such as compassion, integrity, excellence, and inclusion.
• Teach technical outdoor skills appropriate to the course type (e.g. trail & river navigation, camp craft, belaying, paddling strokes, knot tying, food storage).
• Manage the physical, emotional and mental safety and wellbeing of a student group (6-12 participants) 24 hours/day throughout the expedition.

Challenge Course Responsibilities

• Challenge Course Facilitators are responsible for facilitating and monitoring their groups’ day program activities including ground games, team initiatives and high ropes course activities.
• Collaborate with other facilitators and Program Coordinators to plan, facilitate and debrief with participants to meet group goals.
• Promote self-confidence, positive group dynamics, and problem-solving abilities amongst group members through thoughtful progression planning.
• Set up technical challenge course elements and oversee participant safety and emotional well-being while up on the challenge course.

Logistic Responsibilities 

• Provide in-field support including shuttling vehicles, resupplying crews halfway through expedition, supporting crews in rock climbing, and responding to the needs of the expeditions in the field (includes multi-day base camping).
• Support instructors during expedition prep, gear issue, cleanup, and de-issuing.
• Maintain outdoor equipment, including repair, laundry, and inventory.
• Transport crews and individual students into and out of the field along with urban transportation (I.e. School, train station and airport pick-ups and drop-offs).

Community Development

• Commit to actively participating in building a community where all students and staff feel a sense of belonging.
• Provide clear, effective and timely communication with co-instructors, program coordinators, and other staff.
• Be willing and able to give and receive timely, effective oral and written feedback.

**Employment Start and End Dates: March 9 - November 20, 2026**

Knowledge & Abilities

• Collaboration - Ability to work with people from diverse backgrounds to effectively meet shared objectives, while encouraging the open expression of a diversity of ideas and opinions. 
• Communication - ability to clearly convey ideas, facts and information in a variety of settings using different mediums, while encouraging the open expression of a diversity of ideas and opinions. 
• Conflict Management - Ability to manage and resolve conflict productively and with minimal negative impact by integrating a diversity of viewpoints, addressing harm, and fostering understanding and empathy.
• Continual Learning -The ability to assess and recognize one's own strengths and pursue opportunities for continuous improvement through formal and informal channels including feedback, training, or stretch goals. An interest in and commitment to knowing oneself and others.
• Cultural Competence -The ability to recognize and appreciate patterns of cultural differences and commonalities and to shift cultural perspective and change behavior in culturally appropriate and authentic ways. 
• Decision Making - The ability to make sound and timely decisions that accomplish goals, even in the face of uncertainty or high-pressure situations.
• Instills Trust - The ability to gain the confidence and trust of people from varying backgrounds and lived experiences through honesty, integrity, authenticity, and consistency between words and actions. 

Skills

• Risk Management - Ability to lead self and others in anticipating, mitigating, and engaging in healthy risks to meet goals.
• Self-Management - The ability to set well-defined and realistic personal goals, take on and complete tasks in a timely manner, and complete work with an appropriate level of supervision.
• Situational Adaptability - The ability to modify approach and demeanor in real time to align with the shifting demands of different situations. The ability to "read the room" and adjust accordingly.
• Teaching Others - The ability to help others learn through formal and informal methods, identify training needs, provide constructive feedback, and coach others on how to successfully perform tasks.
• Outdoor Technical Skills - Demonstrated competency in skills like canoeing, portaging, backpacking, campcraft, map and compass navigation, expedition logistics and risk management.

Essential Eligibility 

• Must be 21 years or older.
• Must procure and pass an FBI Criminal Records Check prior to employment.
• Must obtain Criminal and Child Abuse clearances for Pennsylvania prior to employment.
• Able to work irregular hours as necessary including the ability to work weekends as assigned.
• Must have a valid driver’s license for a minimum of 3 years at time of hire and a willingness/ability to drive large passenger vans/trailers (upon successful completion of POBS driver training and assessment.)
• Current Wilderness First Responder, or willingness to complete certification prior to Lead Instructor promotion (Available to staff on-site at a reduced price in February).
• Preference for a minimum of two years working in the experiential education field.
• Previous experience in outdoor recreation, education, leadership, or youth programs is preferred but not required.

Physical Requirements

• Able to participate in extended field programs (hiking, paddling, climbing, etc.) in varying weather conditions.
• Able to carry a weighted backpack on backcountry terrain for up to 14 days consecutively.
• Able to work in remote outdoor settings for extended periods.
• Able to be on feet most days, occasionally for up to 16 hours or more in case of emergency.
• Able to carry, lift, and move a minimum of 50 pounds.
• Able to comfortably work at heights of 30-40 feet.

Compensation and Benefits

Entry-level compensation (paid as a daily wage) is as follows:

• Training Rate $120 per diem
• Facilitator $ 125 per diem
• Instructor $ 131 per diem
• On-Base Logistics $ 122 per diem
• In-Field Logistics $ 125 per diem

Per Diem Rate Structure

Per diem rates are tiered and progressive. Rates are determined by both an individual’s experience level and the role worked. Staff may be compensated at different per diem rates based on the responsibilities of the position they are assigned to for a given shift. As staff gain experience and are approved to work in roles with increased responsibility, applicable per diem rates increase accordingly.

Benefits

• Optional staff housing for 4 instructional seasons: $125/month for a bunk room.
• Access to Pro Deals (the opportunity to purchase outdoor gear at discounted rates).
• Access to POBS Employee Assistance Program.

Plus:

• In-house and external professional development opportunities; including Outward Bound Network Staff Invitationals.
• A vibrant staff culture—many team members form lifelong friendships here.

 Application Process

Please apply directly on the POBS career page by January 29th, 2026  and have the following documents ready to upload: 

1. Cover Letter
2. Resume