Kayak Expeditions - Lead Instructor

Job Description

Work with us to make a difference if....

....you believe that kids learn best when they have the chance to experience, touch and feel with their own two hands.

....you believe that that character, and how to be a good person, are the most important things we can teach our kids to lead meaningful lives.

....diverse community is extremely important to you. You cherish opportunities to learn from those around you, and seek out the chance to live and work with people who inspire you.

....the idea of living and working on an island, and watching the sun set over the Boston skyline every night sounds awesome to you.

If you agreed with all of the statements above, look no further, Thompson Island Outward Bound may be right for you!


Established in 1988, Thompson Island Outward Bound Education Center is an independent Massachusetts not-for-profit organization whose mission is to provide adventurous and challenging experiential learning programs that inspire character development, compassion, community service, environmental responsibility, and academic achievement. We serve over 6,500 early adolescents annually from all economic and social communities of greater metropolitan Boston, and the institutions and adults who support them.

In partnership with Boston Public Schools and the National Park Service, our programs utilize the natural resources of Thompson Island to ignite a love of learning, inspire curiosity, and build teamwork in students of all ages. From hands-on field experiences for urban youth to summer wilderness expeditions and professional team building programs, we change lives through challenge and discovery.

POSITION: Lead Instructor – Kayaking Expeditions


Course Director – Retail and Harbor Expeditions


June 11 – September 1, 2018


Full Time, 3 Months (potential to couple with spring and fall opportunities), Seasonal Exemption


Thompson Island – Boston, MA



 Kayaking Expedition Lead Instructors are responsible for leading 7-day, co-ed sea kayaking expeditions in the Boston Harbor for students enrolled in the Boston Public School system, and TIOBEC’s other established school partners. All LIs are required to either hold a current ACA Level 3 Coastal Kayaking certification, or obtain said certification through the instructor certification training that is included as part of the Staff Expedition. An understanding of Outward Bound philosophy and methodology is critical to this position and to the overall success of course leadership. Candidates must display strong paddling, navigation, and group management skills, and demonstrate a firm understanding of course area and structure. Successful candidates will be a minimum of 21 years of age, and have extensive experience leading overnight sea kayak trips. 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 any 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 Harbor Programs Course Director or the Expedition Program Manager


Key Relations:

  • Assistant Instructors
  • Interns
  • Program Operations and Expedition Manager
  • Director of Program Operations and Expeditions
  • Logistics Coordinator


  • 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
  • ACA Level 3 Kayak Instructor certification required
  • 125 minimum verifiable field credits with TIOBEC, OB or similar organization
  • Proficient with navigation
  • Proficient in VHF radio and maritime traffic protocols
  • Proficient in sea kayaking in Level 3 environments or higher
  • 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 commit to the full duration of each course they are instructing
  • Must respond to course delivery needs and/or behavioral/medical needs as prescribed in the TIOBEC 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
  • LIs 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 including 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
  • This position requires a criminal background check


  • 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.  Temporary 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
Job Availability: 

Applications will be processed on a rolling basis.

To Apply

Application Closing Date: 
Applications will be processed on a rolling basis
Application Contact Email: 
Employment Type: 
Job Region: 
Job Location: 
Boston, MA
Job Experience: 
1 - 2 years
Job Degree Level: 
Not Specified
Job Starting Date: 
June 11, 2018

Job Details

Job Details: 
Experiential Education
Group Facilitation & Processing
Outdoor Education Center
Outdoor Skills School
Risk Management
Job Activity: 

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