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Who are we? 

Cathleen Stone Island is a National and State Park located in the heart of the Boston Harbor Islands, With a 200-year legacy of serving children in Boston and a 48-year partnership with the Boston Public Schools (BPS), the Island is a beacon for experiential education, empowering young people through hands-on learning and skill building and outdoor adventure and exploration. We are a proud member of the network of 11 Outward Bound schools in the U.S., with a shared mission to change lives through challenge and discovery.  

Education is at the forefront of our work.  Funded by a combination of philanthropy and a robust private events business, our outdoor educational programs are offered at no cost to families. 

 

What is our mission and how do we achieve it? 

Cathleen Stone Island Outward Bound School’s (CSIOBS) core mission is to build stronger, more equitable school communities by delivering free experiential learning programs that boost academic success and foster personal growth. Our research-based programs blend STEM, social-emotional, and challenge-based learning, giving students a unique opportunity to build life skills alongside academic ones. 

 

Whom do we serve (students, clients, customers) 

We offer programs for Boston Public School middle school and high school students, fee-for-service programs for school and youth groups, and leadership development programs for professionals. We also fund our transformational programs by hosting private and corporate events and weddings. 

 

What is the Opportunity?

The Programs Course Director (CD) is responsible for the overall quality, consistency and safety of the CSIOBS 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 base and are expected to be on call 24 hours a day for the entire duration of their course.

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

 

ESSENTIAL DUTIES AND RESPONSIBILITIES

  • 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 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 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

 

QUALIFICATIONS

  • 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 CSIOBS 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.
  • Wilderness First Responder & CPR certification preferred
  • Intermediate computer skills, working knowledge of Microsoft Office Suite (Word, Excel, and Outlook).
  • Spanish proficiency preferred

 

WORK CONDITIONS

  • Expected ongoing coordination and collaboration with all CDs and Program Managers
  • Courses are dynamic, and demand sound decision-making within the scope of CSIOBS 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

 

PHYSICAL REQUIREMENTS

  • 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.

 

COMPENSATION AND BENEFITS 

Salary commensurate with experience. Employer sponsored health insurance with the option to select between two comprehensive, valuable plans. Premier dental plan. 401(k) retirement plan with competitive match. Generous paid time off including, vacation, holidays, personal days, parental and sick leave. Flexible scheduling, pursuant to position. Work that engages a diverse and dynamic community of educators and learners, with the shared vision of shaping a better future for Boston students. A quality work life in Boston’s vibrant Seaport district with frequent access to the natural wonders and positive impacts of Cathleen Stone Island.

 

Cathleen Stone Island Outward Bound School 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.  

 

Outward Bound has a zero-tolerance policy for incidents of child abuse and neglect. Protecting our minor students against abuse and neglect is of the highest priority.