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


November 29, 2021, 12 months full-time with benefits


Instructors carry out the mission of Thompson Island Outward Bound with students in the field, whether that be delivering programs virtually or in-person. Instructors are responsible for the delivery and overall safety of programs that occur on our island base in the Boston Harbor in the spring, summer and fall, though this position will begin with winter crew classes in Boston Public Schools (or virtual delivery) until March 2022. Working with students in small groups of 8-12, Instructors are responsible for structuring a safe, inclusive and meaningful learning environment for all participants. Through the use of games and initiatives, high and low challenge course elements, expeditionary learning, and group processing and reflection, instructors promote social emotional learning for youth from a wide range of backgrounds for courses virtual or in-person.

If you join us as an instructor, you are committing to being with students for the full duration of each course, from preparation, delivery, to debrief. You will maintain communication with the Course Director while courses are in the field, and 24/7 support to co-instructors and students.  During the school year, you will facilitate our Youth Programs with Boston Public Schools, and during the summer months you will either serve as a Crew Leader for Green Ambassadors, an Instructor for our Summer Learning Expeditions with BPS, or an Expedition Instructor for Summer Expeditions. 


Thompson Island Outward Bound is part of a national network of experiential and outdoor education programs for youth and adults. We use the inherent challenge of the island outdoor spaces, as well as virtual spaces, to teach people of all ages to be compassionate leaders, serve their communities, and build character to ultimately reveal the full potential within all of us.

Our mission is to expand education for students in Boston Public Schools by providing hands-on science education and character-building experiences outside the classroom. Designed to inspire an interest in science and promote the development of social emotional skills, Outward Bound courses run on Thompson Island for one day up to a two-week expedition. The majority of these programs utilize established STEM curriculum based on the Massachusetts State Science Standards, delivered in nature. We also deliver programs that are custom-designed, utilizing the low and high ropes challenge course elements to provide tailored, adventure-based experiences for young people. 


An Educator with Strong Interpersonal Skills

  • Experienced working with youth and/or adults, ages 12-20, in a culturally relevant educational context
  • Possess cultural humility and responsibility: You work effectively with a wide variety of age groups and populations from diverse backgrounds, role modeling inclusive behavior and building positive group culture
  • Passionate about and dedicated to experiential education for youth from communities in Boston and beyond
  • Able to communicate clearly and directly
  • Comfortable giving and receiving feedback
  • Able to build rapport easily with students and colleagues
  • Able to meet different learning-style needs by varying teaching techniques
  • Have prior experience in team building, facilitation, and debriefing in a group setting
  • Have prior field experience in outdoor education programs

Physical & Mental Requirements

  • Comfortable in outdoor settings with facilitation skills in the New England environment, to a level that allows for focus on student experience
  • Sufficiently physically fit to participate in all site and course activities, while maintaining ample energy, strength, and focus to aid students and instructors
  • Can be on feet most days - sometimes for up to 16 hours a day, possibly more in the case of an emergency
  • Comfortable working outdoors, regardless of weather or season
  • Able to practice proper self-care and energy management while in the backcountry, or on multi-day trips, for extended periods of time
  • Able to maintain composure, exercise sound judgment and decision-making, and assess and mitigate risk under extended periods of stress
  • All 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
  • Hold, or are willing to obtain before start of in-person programs, current Wilderness First Aid and CPR. We will support the right candidate in obtaining this certification.

Bonus if you…

  • Have personal experience as, or professional experience engaging with immigrants, first-generation US citizens, English Language Learners, or other non-dominant identities represented in the greater Boston area
  • 1+ years prior field experience in outdoor education programs or similar educational settings
  • Experience working with middle-school populations
  • Speak Spanish, Cape Verdean, Haitian Creole or other languages
  • Hold Wilderness First Responder (WFR) certification or equivalent
  • Have experienced belaying and monitoring students in a climbing or high ropes context


  • Participate in New Instructor Training and in-season professional development
  • Lead and facilitate the following activities: team building initiatives, service learning, low and high ropes elements, and hands-on science lessons.
  • Assist in the design and facilitation of programs in line with the training and mentorship you will receive around Outward Bound’s mission and educational framework 
  • Develop and deliver engaging curriculum appropriate for youth and adults
  • Clearly establish limits and boundaries for student behavior and independence
  • Execute successful course planning, including development of educational and technical curricula, schedule planning, and time management in the field.
  • Manage a student group in emergencies and adhere to all local operating procedures, safety policies and emergency procedures outlined in the staff manual
  • Provide clear, effective and timely communication with the co-instructors, Course Director, and other staff
  • Responsible for supervision on overnight programming including sleeping in dormitories, mealtime, and recreational time.
  • Maintain 100% sight and sound at all times, providing 24-hour emotional and physical support to students, or for the duration of the program.
  • Exercise sound judgment and decision-making. Assess and mitigate foreseeable hazards

Compensation & Schedule

  • This is a full-time, 12 month position with benefits.
  • Food and shared housing provided while on course on Thompson Island
  • Position will be in Boston Public Schools or virtual from November- March, and in-person on Thompson Island from March - November 2022.


  • Competitive salary, commensurate with experience
  • Employer-sponsored health and dental insurance
  • Generous paid time off including vacation, holidays, personal days, parental, and sick leave
  • 401k retirement plan with competitive match
  • Temporary housing provided on Thompson Island when the course requires it
  • Pro Deals, the opportunity to purchase outdoor gear at discounted rates
  • Highly energetic and supportive work environment in a mission-driven organization

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.

Thank You

Your application was submitted successfully.

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