Programs · Boston, Massachusetts
Department Programs
Employment Type Full-Time
Minimum Experience Entry-level

POSITION: Instructor  

REPORTS TO: Course Director Team 

LOCATION: Boston, MA – Thompson Island 



Instructors are responsible for the co-delivery of Youth Programs. A foundational understanding of Outward Bound philosophy and methodologies is critical to this position and to the overall success of course delivery. Candidates must display foundational technical, facilitation, group management skills, and show an understanding of the course area and structure. Successful candidates will be a minimum of 18 years of age and have facilitation and/or trip-leading experience.

A minimum of Wilderness First Aid (WFA) with CPR is preferred for this position. 



  • Full commitment to safety, course outcomes, and student experience 
  • Serve as a Youth Programs Facilitator  
  • Actively participate in pre-course training and briefings, and post-course debriefs 
  • Help ensure prompt execution of their course’s preparation and post-course paperwork and logistics 
  • Help manage any in-field or program transitions 
  • 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 while on course  
  • Deliver course curriculum and remain accountable to student and course outcomes 
  • Enforce Leave No Trace and other pertinent wilderness ethics on Thompson Island and all other program areas 
  • Perform additional duties and responsibilities at the direction of the Course Directors, the Program Managers, and/or the Director of Delivery and Program Operations. 



Key Relations: 

  • Co-instructors 
  • Interns 
  • Course Directors 
  • Program Managers 
  • Director of Delivery and Program Operations 
  • Logistics and Operations Manager 
  • Safety Team 



  • Bachelor’s Degree or two years equivalent field experience preferred 
  • Wilderness First Aid and CPR preferred (or the ability to obtain one during training)   
  • Minimum of ACA Level 2 Kayak Trip Leader certification required for sea kayak applicants (or the ability to obtain said certification during staff training) 
  • Relevant work experience in the following: 
  • Working with participants age 12-18+ 
  • Managing challenging student behaviors 
  • Working with diverse communities 
  • Teaching and facilitation tailored to different learning styles 
  • Teaching and facilitation tailored to different program sites (virtual or in-person) 
  • Experience working on high ropes challenge courses a plus 



  • Must commit to the full duration of each course they are instructing, including preparation, weekends, and overnights if the program requires it 
  • Must respond to course delivery needs and/or behavioral/medical needs as prescribed in the TIOBEC (Thompson Island Outward Bound Education Center) Manual  
  • Expected ongoing coordination and collaboration with all Course Directors and co-instructors 
  • Courses are dynamic, and demand sound decision-making within the scope of TIOBEC methodology 
  • Instructors must be able to manage their course with appropriate autonomy, as determined by the Course Director  
  • Environmental fluctuations are typical of the New England coast, and can include hot, humid weather, and unseasonably cool, rainy, and windy coastal weather; must be comfortable working outside in either of these extremes for extended periods of time  



  • Must be at least 18 years of age 
  • Must be able to lift/carry 50 lbs. 
  • Must be able to be on feet and/or active an average of 8+ hours per day 
  • Must be currently vaccinated against COVID-19 up to CDC guidance (including initial booster and BA.4 + BA.5 booster)



Competitive salary, commensurate with experience. *Employer sponsored health insurance with the option to select between three comprehensive plans. Opt-in premier dental and vision plans. 401(k) retirement plan with competitive match. Generous paid time off including, vacation, holidays, personal days, parental and sick leave.* Flexible scheduling, pursuant to position. Temporary housing is provided on Thompson Island for positions that necessitate. 

*certain benefits are only available to eligible full-time employees*

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. 


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  • Location
    Boston, Massachusetts
  • Department
  • Employment Type
  • Minimum Experience