Lead Instructor- Backpacking

Job Description

START DATE: June 11 - September 1 (Potential to couple with spring/fall opportunities if desired)


Backpacking Expedition Lead Instructors (LIs) are responsible for leading 5-day, co-ed island-based backpacking expeditions on Thompson Island for students enrolled in the Boston Public School system and other established school partners. An understanding of Outward Bound philosophy and methodologies is critical to this position and to the overall success of course leadership. Excellent group management skills and a demonstrated and firm understanding of course area and structure is a must. Successful candidates will have extensive experience leading backpacking and/or climbing trips, and the ability to teach introductory-level expeditionary skills. Current Wilderness First Responder (WFR) certification with CPR required.


  • Must commit to the full duration of each course, including preparation and debrief
  • Full commitment to safety, course outcomes and student experience
  • Actively participate in pre-course trainings and briefings, and post-course debriefs
  • Ensure timely execution of their course’s preparation and post-course gear de-issue
  • Manage expedition re-supply and any other in-field transitions
  • Produce all necessary course paperwork by the prescribed deadline
  • Serve as the point of contact in the field while on course
  • Be familiar with the student medical forms and other pertinent participant information
  • Maintain communication with the Course Director while courses are in the field
  • Provide written and verbal evaluation of co-instructors and Course Directors necessary for their Individual Development Plan (IDP) and improved delivery of future courses
  • Provide 24/7 support to co-instructors and students
  • Deliver course curriculum and remain accountable to student and course outcomes
  • Take on an active role in the development of Assistant Instructors and Interns
  • Enforce Leave No Trace (LNT) principles and other pertinent wilderness ethic on Thompson Island and all other program areas
  • Perform additional duties and responsibilities at the direction of the Land Programs Course Director or the Expeditions Program Manager


  • Bachelor’s degree preferred
  • 2-3 years relevant field experience in the following:
    • Working with adolescents age 12-16
    • Managing challenging behaviors
    • Working with diverse communities
    • Working with unique learners
  • Wilderness First Responder & CPR certification required
  • 125 minimum verifiable field credits with TIOBEC, OB or similar organization
  • Proficient in backpacking and survival skills
  • Proficient in climbing
  • Proficient with navigation
  • Experience managing high ropes challenge courses a plus
  • Experience working with diverse communities
  • Sound judgement and decision making skills within the scope of TIOBEC Charter Operating Policies and Procedures
  • Able to manage course with appropriate autonomy, as determined by the Course Director


  • Must be at least 21 years of age
  • Positions reporting hours to the island, are asked to assist loading/unloading cargo from the boat as able.This involves lifting and walking with parcels upwards of 50lbs on and off moving docks and up/down ramps
  • Must be able to be on feet and/or active an average of 8+ hours per day


Competitive daily pay commensurate with experience. Earned Sick Time. 401K retirement plan with competitive match once pre-requisites are met. Worker’s Compensation Insurance. Access to professional discount programs for gear and clothing.Housing provided on Thompson Island for positions that necessitate.

Thompson Island Outward Bound Education Center is an equal opportunity employer and actively seeks staff as diverse as the communities it serves. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law.

Job Availability: 

This positions starts June 11, 2018 and lasts for 3 months, with the ability to couple with Spring and Fall employment.

To Apply

Please submit a resume and cover letter detailing your interest in the position to [email protected]. We look forward to hearing from you!

Application Closing Date: 
Not Specified
Application Contact Email: 
Employment Type: 
Job Region: 
Job Location: 
Thompson Island, Boston Harbor, MA
Job Experience: 
3 - 5 years
Job Degree Level: 
Job Starting Date: 
June 11, 2018

Job Details

Job Details: 
Experiential Education
Outdoor Education Center
Job Population: