Summer Learning Expeditions Instructor

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

POSITION: Summer Learning Expeditions Instructor

REPORTS TO: Program Course Directors

START DATE: June 15th, 2021

DURATION: Full Time, 3 Months (potential to couple with fall opportunities)

LOCATION: Thompson Island – Boston, MA


Program Instructors for Summer Learning Expedition are primarily responsible for the delivery and overall safety during the 21-day, backpacking or sea kayaking expedition and field science-based programming on Thompson Island. After the 21-day course, instructors will deliver one and two-day programming on the island for the duration of the summer. Candidates must display strong technical, facilitation, and group management skills, and demonstrate a firm understanding of course area and structure. Experience in backpacking or sea kayaking is strongly preferred, but not required.


Working with students in groups of 8-12, Instructors are responsible for structuring a safe, inclusive, and fun learning environment for all participants. Using games and initiatives, high and low challenge course elements, hands-on-science lessons, and group processing and reflection, facilitators promote teamwork, character development, perseverance, and effective communication for youth from a wide range of backgrounds, and of varying ages.


Successful candidates will have trip-leading experience.


Wilderness First Aid and CPR required. Wilderness First Responder (WFR) with CPR is strongly preferred.




  • Actively participate and contribute to all pre-season training and in-season professional development sessions.
  • Prepare and facilitate multi-week expedition that includes; teambuilding games and initiatives, high and low challenge course elements, and hands-on-science lessons in accordance with course outcomes and student needs.
  • Attend all pre-course prep meetings, and post-course debriefs
  • Collaborate with co-instructor(s), Course Directors, and the Logistics team to ensure all students are equipped with appropriate gear and clothing for the weather and activity.
  • Deliver clear and concise course expectations, activity instructions, and safety expectations to all participants.
  • Responsible for supervision of overnight programming.
  • Maintain 100% sight and sound at all times, providing emotional and physical support to students for the duration of the course.
  • Facilitate prompt arrival to designated locations with students; maintain awareness and understanding of daily schedules.
  • Responsible for daily program setup & cleanup and maintaining care for the organization’s resources and supplies.
  • Complete professional and timely paperwork following the conclusion of every course.
  • Respond to course delivery needs and/or behavioral/medical needs in accordance with TIOBEC policy and procedure and COVID-protocols.
  • Demonstrate a commitment to OBUSA safety standards and TIOBEC Charter Operating Policy and Procedures.



Key Relations:

  • Co-facilitators
  • Course Director Team
  • Program Manager & Director
  • Logistics Team
  • Safety & Site Management Team



  • Bachelor’s degree in related field preferred OR 2-3 years experience working directly with youth in one or more of the following fields:
    • Environmental education/field-based science education
    • Challenge Course Facilitation
    • Informal education/youth development
    • Outdoor education/recreation
    • Summer Camps
  • 1-2 years of experience working with urban youth
  • Experience in a working environment with middle-school students
  • Experience with behavior and group management a plus
  • Experience with Challenge Course or climbing a plus
  • Current Wilderness First Aid and CPR Certifications required, Wilderness First Responder preferred
  • Strong interpersonal skills, ability to give and receive appropriate and timely feedback
  • Ability to effectively facilitate teambuilding activities, foster leadership skills, and cultivate positive group dynamics in groups of students
  • Ability to work both independently and as part of a team
  • Ability to dependably serve as a positive role model to students and peers at all times
  • Demonstrated ability to communicate and present ideas with clarity, credibility, humility, and tact
  • Proven success operating in dynamic and changing environments
  • Demonstrates sound judgment.
  • Dual language speaker a plus
  • Experience working with students with cognitive learning disabilities is a plus



  • ACA L2 Trip Leader Certification preferred
  • Proficient in backpacking and/or sea kayaking
  • Proficient in camp craft and survival skills



  • Will be required to live on the island for the duration of all overnight programs, and there is the potential for some over-night training requirements
  • Expected ongoing coordination and collaboration with all Course Directors and co-instructors
  • 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
  • Work with students 24 hours/day for the entire duration of the course (1-21 days), with rotational breaks amongst co-staff.


  • Must be able to carry a 50+lb backpack, sit in a kayak for 4+ hours, and willing to camp for 2+ weeks.
  • All positions reporting hours to the island are asked to assist in 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
  • Must be currently vaccinated against COVID-19 up to CDC guidance


Competitive daily pay commensurate with experience. Earned Sick Time. 401K retirement plan with competitive match once pre-requisites are met. Worker’s Compensation Insurance. Accident Insurance. Access to professional discount programs for gear and clothing.  Temporary housing is provided on Thompson Island for positions that necessitate. Possibility for fall employment, depending on experience, interest, and qualification.


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