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Programs Course Director

  • Full time
  • Boston

Website Thompson Island Outward Bound Education Center

POSITION: Programs Course Director

REPORTS TO: Program Manager Team

START DATE: March 6, 2023

DURATION: 9-month, full-time (potential to convert to year-round)

LOCATION: Thompson Island – Boston, MA



The Programs Course Director (CD) is responsible for the overall quality, consistency, and safety of the Thompson Island Outward Bound (TIOB) courses (virtual or in-person). A candidate for this role needs to demonstrate an outstanding ability to supervise and train others, as well as have experience leading youth programming. The Course Director’s primary role is to ensure course delivery meets program standards for safety and quality. While in the field, Course Directors will observe and mentor staff, focusing on course safety, instructor development, and educational outcomes. Course Directors should be at a level of skill with their course elements wherein they could comfortably replace a Lead Instructor in the field if the need presented itself. The Course Director is also often at base coordinating with other departments, islands, or outside entities to ensure the courses in the field run safely and smoothly. Course Directors must display the highest level of professionalism, dedication, and commitment to safety both in the field and at the base and are expected to be on call 24 hours a day for the entire duration of their course.

The course director reports to the Program Director, who reports to the Chief Education Officer.

Wilderness First Responder (WFR) and CPR certification are preferred for this position.



Ensure the delivery of the Outward Bound Mission and educational programming, including Social Emotional Learning Frameworks, by the instructional teams.
Support course delivery through supervisory visits to the field to provide logistical support, conduct coaching observations, and mentor field staff.
Ensure course delivery aligns with TIOBEC’s instructional tools, preferred practices, and policies and procedures.
Provide 24/7 support to field staff to manage medical or behavioral evacuations and early departures; arrange medical support; manage impending inclement weather that may necessitate itinerary adjustment, and any other potential or real threat to safety or course objectives
Ensure timely execution of instructor course prep and post-course wrap-up
Produce all necessary course paperwork by the prescribed deadline
Provide consistent and professional communication with staff, students, and families during and post-course.
Make necessary arrangements with kitchen, waterfront, site management, staffing, and all other aspects of Thompson Island as necessary for course delivery
Manage student medical forms and other paperwork
Provide written and verbal evaluation of instructors necessary for their Individual Development Plan (IDP) and improved delivery of future courses
Maintain communication with the Program’s Manager and/or the Director of Delivery and Program Operations as directed
Active participation in student recruitment efforts, including in-school recruitment events and island-based open houses
Utilize the Delphi system and Participant Management Database in order to support programs, as needed, creating internal forms to communicate client needs, tracking and updating operations and ferry information, etc.
Work with the Program Directors, Managers, and other Course Directors to deliver staff trainings and PDs.
Serve as a Connections and Discovery Program Course Director or Instructor, as dictated by staffing needs
Work with assigned Summer Program Manager on the design and execution of assigned summer programming
Perform additional duties and responsibilities at the direction of the Program Manager Team and/or the Director of Delivery and Program Operations




Lead Instructors
Instructors and/or Crew Leaders

Key Relations:

Director of School Programs
School Programs Delivery Manager
Logistics and Operations Manager
Program Managers
Director of Safety and Training
Site Management Team
Safety Team
MVOB Captains and Deckhands



  • Bachelor’s degree preferred
  • 3-4 years of relevant field experience in the following: Working with participants ages 11-18+
  • Managing challenging student behaviors
  • Working with diverse communities
  • Teaching and facilitation tailored to different learning styles
  • Teaching and facilitation tailored to different program sites (virtual or in-person)
  • 2-3 years relevant management experience, including training, development, and management of staff, OR 2-3 years direct experience with Thompson Island
  • Outward Bound Expeditions
  • Ability to demonstrate emotional regulation, good judgment, and balanced decision-making in stressful situations.
  • Serve as a role model for students, staff, and the community; able to manage a range of student behaviors in a positive and professional manner.
  • Ability to build and maintain a positive group culture.
  • Flexible, adaptable, and open to change.
  • Wilderness First Responder & CPR certification preferred
  • Intermediate computer skills, working knowledge of Microsoft Office Suite (Word, Excel, and Outlook).
  • Spanish proficiency preferred



Expected ongoing coordination and collaboration with all CDs and Program Managers
Courses are dynamic, and demand sound decision-making within the scope of TIOBEC methodology
CDs must be able to manage their course(s) with appropriate autonomy
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
Must be available for course support 24 hours a day for the duration of the course
Must respond to course delivery needs and/or behavioral/medical needs as prescribed in the TIOB manual
This position requires a criminal background check



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 and down ramps
Must be able to be on feet an average of 3+ hours per day
Able to work through inclement weather conditions that include heat, rain, snow, or cold.


Must be currently vaccinated against COVID-19 up to CDC guidance


Competitive salary, commensurate with experience. Employer-sponsored health insurance with the option to select between three comprehensive plans. Opt-in premier dental and vision plans. 401(k) retirement plan with a competitive match. Generous paid time off including, vacation, holidays, personal days, and parental and sick leave. Flexible scheduling, pursuant to the position. Temporary housing and meals are 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 protected by law.

To apply for this job please visit

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