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: Kayak Expeditions - Lead Instructor

START DATE: June 11, 2017 

DURATION: Full Time, 3 Months (Many instructors will also couple with Spring and Fall opportunities), Seasonal Exemption

Kayak Program Lead Instructors (LIs) are responsible for leading 7-day, co-ed sea kayak courses in the Boston Harbor and Massachusetts Bay. 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 methodologies 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 have extensive experience leading sea kayak trips. Current Wilderness First Responder (WFR) certification with CPR required.


  • 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 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 wr


  • 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
  • Experience working with high ropes challenge courses a plus
  • 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
Job Availability: 

Applications will be processed on a rolling basis.

To Apply

TO APPLY: Please apply using our online application HERE: https://thompsonisland.org/about/employment/field-staff-application/



Application Closing Date: 
Applications will be processed on a rolling basis
Employment Type: 
Job Region: 
Job Location: 
Boston, MA
Job Experience: 
1 - 2 years
Job Degree Level: 
Not Specified
Job Starting Date: 
June 11, 2017

Job Details

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

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