Assistant Instructor- Kayaking

Job Description

POSITION: Assistant 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 Assistant Instructors (AIs) are responsible for co-leading 7 day, co-ed youth kayaking expeditions in the Boston Harbor for students enrolled in the Boston Public School system, and TIOBEC’s other established school partners. AIs work closely with a Lead Instructor to ensure the safety of all course participants and delivery of course outcomes. This position requires the same maturity and skills as a Lead Instructor but allows space for a newer instructor or someone new to Thompson Island to strengthen their skill set, while developing knowledge of Outward Bound methodology, Thompson Island, and our course area. Assistant Instructors work in the field under the mentorship of a Lead Instructor and may in turn mentor an intern. Most AIs work for at least one season before becoming a Lead. Ideal applicants are required to hold at least an ACA Level II Coastal Kayaking certification, or obtain said certification through the instructor certification training that is included as part of the Staff Expedition. Wilderness First Responder (WFR) certification and 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 course preparation and post-course gear de-issue
  • Help manage expedition re-supply and any other in-field transitions
  • Produce all necessary course paperwork by the prescribed deadline
  • 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
  • Deliver course curriculum and remain accountable to student and course outcomes
  • Provide 24/7 support to co-instructors and students
  • Take on an active role in the development of Interns
  • Enforce Leave No Trace and other pertinent wilderness ethics on Thompson Island and in all other course areas
  • Perform additional duties and responsibilities at the direction of the Harbor Programs Course Director or the Expeditions Program Manager



Key Relations:

  • Lead Instructors
  • Interns
  • Kayaking Expeditions Course Director
  • Program Operations and Expeditions Manager
  • Logistics Coordinator



  • Bachelor’s degree preferred
  • 1-2 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 (WFR) & CPR certification
  • 75 verifiable field credits with TIOBEC, OB or similar organization
  • Proficient in sea kayaking in Level 3 environments or higher
  • Proficient with navigation
  • Proficient in VHF radio and maritime traffic protocols
  • Experience managing high ropes challenge courses a plus
  • ACA Level 2 Coastal Kayak certification required
  • Experience working with diverse communities



  • Must commit to the full duration of each course they are instructing
  • Must respond to course delivery needs and/or behavioral/medical needs in accordance with TIOBEC policy and procedure
  • 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 policy and procedure
  • 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 21 years of age or older
  • 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.

There may be multiple Assistant Instructor positions available.

 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.


Job Availability: 

This positions starts June 11, 2018 and lasts for 3 months, with the ability to couple with Spring and Fall employment.

To Apply

1. Apply using our online application found on our employment page -
2. Qualified applicants with completed applications will be contacted for an initial, phone-screening interview to begin the interview process.

Application Closing Date: 
Not Specified
Application Contact Email: 
Employment Type: 
Job Region: 
Job Location: 
Thompson Island, Boston Harbor, MA
Job Experience: 
1 - 2 years
Job Degree Level: 
Job Starting Date: 
June 11, 2018

Job Details

Job Details: 
Experiential Education
Outdoor Education Center
Job Population: