Our 12-week-long Apprenticeship is intended for individuals who are interested in working towards a career as a POBS Instructor.

Apprentices experience extensive classroom and in-field training. The Apprenticeship includes:

  • Expedition training
  • Day program facilitation training
  • Classroom training in Outward Bound history and philosophy, student management, conflict resolution, safety and risk management, diversity and inclusion, curriculum development, and more
  • Technical skills training: Backpacking, canoeing, top-rope rock climbing, high ropes, Aerial Teams Course
  • Opportunities to participate in backpacking and/or canoeing expeditions as a “third Instructor”
  • Opportunities to work center-based team building programs alongside experienced Instructors
  • Logistics: Gear maintenance and repair, vehicle maintenance and driver training, vehicle shuttles, base site projects

Upon successful completion of the Apprenticeship, individuals  are likely to transition into the Instructor role and lead backpacking, rock climbing, canoeing, and/or daylong teambuilding programs.

Please fill out our application online and indicate the position for which you wish to apply.


  • Participate in expedition, classroom, and day program trainings
  • Participate in expedition instruction and day program facilitation alongside experienced instructors
  • Practice clear, effective, and timely communication and feedback
  • Practice teamwork, cooperation, and inclusion
  • Assist with student supervision, field evacuations, and other various program tasks as needed
  • Assist with logistical functions such as food preparation, vehicle shuttles, equipment resupplies, and gear maintenance and repair
  • Adhere to all Outward Bound Field Policies and Procedures outlined in the manual
  • Adhere to all policies outlined in the Employee Handbook


  • Passion for working with youth
  • Commitment to Outward Bound's mission and values
  • Exceptional interpersonal skills
  • Commitment to equity, inclusion, and justice for all
  • Enthusiasm for serving participants with a diversity of identities, backgrounds, perspectives, and lived experiences
  • Ability and willingness to deliver and receive feedback
  • Ability to respond creatively, flexibly, and compassionately to the needs of our participants
  • Wilderness First Responder certification (or willingness to obtain certification within one year of hire date)


  • 21 years or older
  • Possess valid driver’s license and at least three years driving experience
  • Procure and pass Pennsylvania Access to Criminal History, Child Abuse Clearance, FBI Background Check, and Motor Vehicle Record Screening
  • Able to be on feet most days, occasionally for up to 16 hours
  • Able to carry, lift, and move a minimum of 50 pounds


  • Apprenticeship: $200/week stipend
  • Philadelphia Outward Bound School curriculum and facilitation training
  • Philadelphia Outward Bound School technical skills training
  • In-house and external professional development opportunities
  • Upon promotion to Instructor, compensation switches to per diem pay (base rate $85/day; pay increases with number of days worked)
  • Optional staff housing offered pending available space, food staples included


Apprentices can anticipate a dynamic and flexible schedule. No two days look the same! The Apprenticeship schedule is released in two- to three-week periods. Though the schedule is irregular, Apprentices can anticipate a ratio of five days on to two days off. Applicants who have external commitments are still encouraged to apply; there may be ways to accommodate.