Program Course Director

Cathleen Stone Island Outward BoundBoston, MA
Onsite

About The Position

The Programs Course Director (CD) is responsible for the overall quality, consistency and safety of the Cathleen Stone Island Outward Bound (CSIOBS) courses. 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 often coordinating with other departments, islands or outside entities to ensure the courses run safely and smoothly. Course Directors must display the highest level of professionalism, dedication and commitment to safety both in the field and at base and are expected to be on call 24 hours a day for the entire duration of their course.

Requirements

  • Bachelor’s degree preferred
  • 3-4 years 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 and program sites
  • 1-2 years relevant management experience, including training, development and management of staff.
  • Ability to demonstrate emotional regulation, good judgement and balanced decision-making in stressful situations.
  • Serve as role model for students, staff and 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 required
  • Intermediate computer skills, working knowledge of Microsoft Office Suite (Word, Excel and Outlook).
  • Must be currently vaccinated against COVID-19 up to CDC guidance

Nice To Haves

  • Spanish proficiency preferred

Responsibilities

  • Ensure the delivery of the Outward Bound Mission and educational programming by the instructional teams.
  • Support course delivery by providing logistical support, conducting coaching observations, and mentoring field staff.
  • Ensure course delivery aligns with CSIOBS’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 Cathleen Stone Island as necessary for course delivery
  • Manage student medical forms and other paperwork
  • Provide written and verbal evaluation of instructors necessary for their professional growth and improved delivery of future courses
  • Maintain communication with the Program’s Team Admin (including program managers, coordinators and directors)
  • Participate in student recruitment efforts, including in-school recruitment events and island-based open houses
  • Utilize booking and client management systems (Triple Seat and Salesforce) 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 training and PDs.
  • Serve as a Connections, Green Ambassadors, or a Discovery Program Course Director or Instructor, as dictated by staffing needs
  • Work with assigned Program Manager on the design and execution of assigned summer programming
  • Perform additional duties and responsibilities at the direction of the Program Manager
© 2026 Teal Labs, Inc
Privacy PolicyTerms of Service