Youth Program Facilitator

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United States

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Youth Program Facilitators are responsible for the delivery and overall safety of school-year programs on Thompson Island. Facilitators promote teamwork, problem solving, character building, and effective communication through comprehensive group processing and reflection. Facilitators will utilize group games and initiatives and low and high challenge course elements to accomplish program-specific goals in a safe, positive, and fun learning environment.  Serving students from a wide range of backgrounds, and of varying ages, Youth Program Facilitators will facilitate both Discovery and Connections programs in the spring and fall seasons:


Connections Programs serve middle schools in the Boston Public School district, and run on Thompson Island for one to three days, including overnights.  The Connections program strives to increase interest in science learning and the development of social emotional skills in Boston’s middle school students.  The majority of these programs utilize established STEM curriculum, based on the Massachusetts State Science Standards, to foster hands on learning experiences in the natural environment. 


Discovery Programs serve a diverse range of ages and populations, from Boston-area youth to University age students on courses lasting in length from 1-3 days. Discovery programs are custom-designed, and seek to provide tailored, adventure-based experiences for young people.



  • Actively participate and contribute to all pre-season trainings and in-season professional development sessions
  • Prepare and facilitate teambuilding games and initiatives, high and low challenge course elements and Environmental Education lessons in accordance with course outcomes and student need (day, overnight, and multi-day expeditions).
  • Attend pre-course meetings, collaborate with co-instructor to plan course activities that meet programmatic and client objectives
  • Collaborate with co-instructor(s), Course Director and Logistics Manager to ensure all students are physically equipped with appropriate clothing and gear per the time of season and fitting to the experience
  • Deliver clear and concise course expectations, activity and safety instructions to all participants
  • Review and maintain familiarity with student medical paperwork, administer and log student medications as necessary
  • Responsible for supervision on overnight programming including sleeping in dormitories, mealtime, and recreational time.
  • Maintain 100% sight and sound at all times, providing 24-hour emotional and physical support to students
  • Facilitate prompt arrival to designated locations with students; maintain awareness and understanding of daily schedules.
  • Responsible for daily program setup & cleanup, attending course briefs and debriefs, and maintaining care for the organization’s resources and supplies.
  • Complete professional and timely paperwork following the conclusion of every course.
  • Participate in post-course debrief and feedback sessions as designated.  
  • Respond to course delivery needs and/or behavioral/medical needs in accordance with TIOBEC policy and procedure.
  • Demonstrate a commitment to OBUSA safety standards and TIOBEC Charter Operating Policy and Procedures.



  • Bachelor’s degree in related field preferred.
  • 1-2 years’ experience working directly with youth in one or more of the following fields:
  • Environmental education/field-based science education
  • Informal education/youth development
  • Outdoor education/recreation
  • 1-2 years of experience and investment in working with urban and at-risk youth.
  • Significant experience with behavior and group management required.
  • Current Wilderness First Aid (WFA) and CPR Certifications.
  • Strong interpersonal skills, ability to give and receive appropriate and timely feedback.
  • Ability to effectively facilitate teambuilding activities, foster leadership skills, and cultivate positive group dynamics in groups of students.
  • Passion for developing middle school students in their growth socially and academically.
  • Knowledge of the flora and fauna of the Massachusetts coastline, or an interest and ability to learn quickly.
  • Ability to work both independently and as part of a team.
  • Ability to dependably serve as a positive role model to students and peers at all times.
  • Demonstrated ability to communicate and present ideas with clarity, credibility, humility and tact: professional attitude and demeanor.
  • Proven success operating in dynamic and changing environments.
  • Ability to reflect on progress against goals for self and others while recognizing and addressing barriers to progress.
  • Possesses openness, responsiveness, approachability, and understanding of others’ perspectives with the demonstrated ability to maintain and build relationships through collaboration.
  • Demonstrates sound judgment.
  • Passion for experiential education.
  • Must be able to commit to the full duration of each course scheduled to facilitate (generally 1-3 days in duration).




  • Must be at least 21 years of age
  • All 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. Accident Insurance. Access to professional discount programs for gear and clothing.  Temporary housing provided on Thompson Island for positions that necessitate. Possibility for summer employment, depending on experience, interest and qualification.

How to Apply:

To apply for Programs Positions:

1. Apply using our online application linked here:
2. In the online application, attach a current resume, and send the reference form link to at least two references to complete your application.
3. Qualified applicants with completed applications will be contacted for an initial, phone interview to begin the interview process.

Please visit our website Employment Page for all othe openings:

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