Experiential Programs Director — Outdoor Ed

Cathleen Stone Island; Boston (MA); On-site; USD 28,140 - 40,078; Full time

Benefits offered by this job

Health insurance

Dental and vision plan

401(k) retirement plan with match

Paid time off

Job summary

Cathleen Stone Island Outward Bound School in Boston’s Seaport seeks a dedicated Course Director to oversee safety and quality of CSIOBS courses, mentor staff, and coordinate with departments to deliver field programs.

You will be on call 24 hours during courses, manage logistics, complete paperwork, and ensure student welfare. Willingness to obtain Wilderness First Aid/CPR if needed is expected.

Qualifications

• Bachelor’s degree preferred
• 3‑4 years relevant field experience, 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)
• 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 Team.

Job description

Cathleen Stone Island Outward Bound School in Boston’s Seaport seeks a dedicated Course Director to oversee safety and quality of CSIOBS courses, mentor staff, and coordinate with departments to deliver field programs.

You will be on call 24 hours during courses, manage logistics, complete paperwork, and ensure student welfare. Willingness to obtain Wilderness First Aid/CPR if needed is expected.