Field Staff and Instructional Positions (Programs Staff)

As a member of our Field Staff and Instructional Team on Thompson Island your primary responsibility will be to provide participants with a safe learning environment and opportunity to engage in activities that allow for learning and growth while exploring places and concepts new to them. All courses are designed to enable the development of compassion, self-confidence, leadership skills, environmental stewardship and a sense of the rich history and habitats associated with our island and surrounding course areas. By the end of each course, be it one day, a multi-week long expedition or a summer long learning program, you will have been given the opportunity to lead a group of students through a sequence of increasing challenges and have fostered their ability to do more as an individual and as a member of team. The positive impact you have on each student can be everlasting and the reward for providing that experience, immeasurable.


Interns add tremendous value to our seasonal staff community while being offered the opportunity to take an active learning role alongside more senior and experienced staff members. Often times our most effective and qualified staff began their Outward Bound or experiential education careers with an internship tailored to developing those interests. Support for those filling internship positions is provided by program management through an Individual Development Plan (IDP) and additionally through the mentorship of more senior staff, peer evaluations and an intentional schedule and progression of skill building.

Students enrolled in a degree program related to education or outdoor leadership can apply to fulfill their internship requirement with Thompson Island Outward Bound Education Center – a well-known and reputable organization in the Outdoor Education industry. Any requirements form an applicant’s College or University should be submitted and approved during the application process.

2014 Internship Opportunities
Due to an overwhelming response from highly qualified candidates we are no longer accepting
resumes for 2014 Internships.

Expedition Interns (Dates: June 2nd – August 22nd) An Expedition Intern begins his or her time on Thompson Island by participating in a week-long Outward Bound staff expedition training, followed by trainings offered to all staff: challenge course and belay monitor, facilitation and student management. Expedition Interns are responsible, throughout the internship period and expedition season, for assisting in administrative, logistical and programmatic processes that help to ensure a course’s success. Working with and assisting instructional staff, program directors, Logistics and Admissions, interns obtain first hand and behind the scenes experience, invaluable to a future leadership role. Essential for this position is technical skill at the level to which one has the ability to keep themselves safe within the context of the program area’s course elements (for example: a Kayak Intern should be able to safely navigate themselves across a channel but do not necessarily possess the skills yet to lead a group across a channel). Ideal candidates for an internship with Expeditions will possess an intermediate level of skill in given course element (either Kayak, Sail or Land), have had experience with expeditionary methodology by way of an Outward Bound course or the like, possess a high level of accountability, be self-motivated, flexible, open to feedback, ready to learn and be willing to spend at least some of their time sleeping under the stars and calling it work. Current Wilderness First Aid (WFA) and CPR certifications required for this internship.

Logistics Internship The Logistics intern is responsible for assisting the Logistics Manager and/or Logistics Team with the daily operations of the Logistics Department. The Logistics Department is responsible for providing food, materials, and equipment essential to the functions of all Thompson Island Outward Bound programs. Additionally, the Logistics Department assists with the maintenance and upkeep of island-wide safety and operational systems, campsites, and facilities. The primary internship duties may include readying supplies and equipment for urban and wilderness programs, implementing and improving efficient issue/de-issue systems, and craftsmanship through repair and maintenance of gear and equipment. The logistics Intern will gain a greater understanding of the functions necessary to support safe and effective urban, front country, and backcountry programs. The ideal candidate possesses a passion for organization and efficient work habits, knowledge of contemporary outdoor gear and clothing, and attentiveness to details.

Summer Connections Intern (Dates: June 16th – August 8th) A Summer Connections intern is responsible for assisting in the administrative, logistical and programmatic implementation of the Summer Connections program. Working with rising 5th grade students as well as professional and part-time educators, the person should be comfortable in front of groups of students and working with other adults in an educational or enrichment setting. This person will be responsible for completing tasks as assigned by the Program Director or their designated manager. An interest in in education, environmental science or experiential education is strongly encouraged. Essential for this position is the ability to provide appropriate and timely feedback to the Program Director, Curriculum Programs to enhance program implementation. Opportunities exist for professional development in shadowing facilitative staff, participating in organizational trainings or direct mentorship. Ideally, this person will have had some experience with Thompson Island, the Boston Public School system or the Boston Harbor Islands. CPR and First Aid a plus but not required for this particular internship

Discovery Program and Environmental Connections Facilitators

(August 25 – October 31)

Discovery Program
Discovery Program Facilitators possess extensive knowledge of experiential programming and group processing skills through the use of games, initiatives, and challenge course elements. Facilitators are responsible for delivering customized programming for a diverse range of ages and populations. These single to multi-day programs focus primarily on character development, leadership, community building and social and environmental responsibility. The majority of these programs utilize the low and high challenge course elements; prior experience with challenge course elements and/or an ACCT Level 1 certification are a plus. Successful candidates may also come to TIOBEC with a variety of other relevant skill sets and backgrounds; student management skills and prior teaching experience are a plus. These positions also help to facilitate our Environmental Connections programs (see description below) in the spring and fall seasons. Current Wilderness First Aid (WFA) and CPR certifications required.

Environmental Connections Program
Our “Environmental Connections Program,” which runs during our spring and fall sessions, was developed through a partnership with Boston Public Schools (BPS), the National Park Service (NPS), and Thompson Island Outward Bound Education Center (TIOBEC). It is based on a three-day, two-night model delivered on Thompson Island in the Boston Harbor. This program serves 6th-8th grade students from our BPS partner schools. Facilitators lead team building initiatives, manage students on low ropes challenge courses; manage students during meals, evening activities and overnight in their dorms on Thompson Island. National Park Service Rangers deliver environmental curriculum. While facilitators assist in delivery of the environmental curriculum, their primary focus then is on group and student management. This position offers valuable training and experience for educators, facilitators and outdoor professionals alike. Many of our Environmental Connections Staff will naturally transition to our “Summer Connections Program” following their spring season with us. These positions also help to facilitate our Discovery programs (see description above) in the spring and fall seasons.

Serving almost 4,000 students, our Harbor Connections program is our most prolific curriculum offering. This program aims to reach Boston Public School students both in the classroom and out on the Harbor Islands. Facilitators for this program will work with our National Park Ranger partners and Curriculum Delivery Specialists to administer in-class lessons to schools in neighborhoods across the city. Students who participate in lessons have the opportunity to then come out to the harbor islands to learn hands-on about the lessons taught in the classroom- experientially engaging in the science and bringing the classroom experience alive. Our Harbor Connections facilitators also participate in leading those expeditions to the islands, and are integral in facilitating the student educational experience. Current Wilderness First Aid (WFA) and CPR certifications required.

Summer Connections Facilitators

(June 16th – August 8th)

The Summer Connections Program is an innovative partnership with Boston Afterschool and Beyond and the Boston Public Schools that serves to help close the academic achievement gap. The Summer Connections program brings students on and off the island each day, Monday through Friday, to engage in out-of-school-time (OST) learning. Thompson Island staff aid this program by assisting Boston Public School teachers in a classroom setting and National Park Rangers in various environmental settings while also helping with lesson plans and overall student management throughout the day. This staff team takes lead on facilitating team building and leadership activities for their students during specific blocks of time during the week to augment their academic blocks.

Green Ambassadors Crew Leaders

(June 16th – August 15th)

Crew Leaders
Green Ambassador Crew Leaders have experience in both the essential technical and interpersonal skills needed to assure projects are completed in a safe, efficient, and team-based manner with high-quality results. Crew Leaders will be selected to co-lead a crew of 10 to 12 Crew Members. These students are 15 to 18 years old, come from a diverse array of backgrounds, and travel from urban communities in Boston. Crew Leaders work alongside Youth Jobs participants on service projects throughout the Harbor Islands and in urban Boston neighborhoods. Development and educational activities occur throughout participants’ time in the Youth Jobs program, be that over the course of one summer or up to four years as returning youth staff. These may include manual service projects, gaining skills in cross-cultural communication and group living, and educational/vocational planning. In addition each crew will participate in one to two, overnights on a Harbor Island working with their crew in a field camp setting; camp craft and outdoor leadership skills are a plus. Crew Leaders are responsible for developing these and other activities for Youth Staff with the support of the Program Manager and a Course Director.
Current Wilderness First Aid (WFA) and CPR certifications required.

Expedition Instructors – Sailing, Kayaking and Land-based

(Dates: June 2nd – August 22nd)

Expedition Instructors are responsible for leading 7-14 day expeditions on Boston Harbor and Massachusetts Bay course areas and on Thompson Island throughout the summer. Both our 7 day island based expedition and our 12 day kayaking expeditions are run as single gender courses and serve students ages 12-14. Our sailing courses are run as both 12 day single gender expeditions for students age 12-13 and 14 day coed trips for older students, ages 14-17. Expedition Instructors present a wide range of outdoor leadership and group management skills, a clear understanding of Outward Bound pedagogy, expeditionary learning and sustainable practices in wilderness contexts. In addition each course element employs its own specific set of specialized skills that instructors must be able to both perform and teach.

Lead Instructors – Sailing Expeditions

    Lead Instructors on our sailing courses are primarily responsible for the physical and emotional safety of students throughout their course, both on board the boat and on land. An understanding of and sincere belief in the Outward Bound philosophy is critical to this position and to the overall success of course leadership. Lead instructors need to display a wide range of outdoor leadership skills and a high level of comfort aboard a sailing vessel. They should be able to comfortably lead group activities and initiatives in dynamic and harsh environments and display compassionate yet affective student and group management abilities. Current Wilderness First Responder (WFR) certification with CPR required.

Lead Instructors – Kayak Expeditions

    Kayak Instructors are responsible for leading twelve-day, single gender kayak courses for 12-13 year old girls or boys in Massachusetts Bay. All lead instructors will be required to pass a level III ACA Certification that is included as part of instructor training. An understanding of Outward Bound philosophy and methodologies is critical to this position and to the overall success of course leadership. Candidates must display strong paddling, navigation, and group management skills, and demonstrate a firm understanding of course area and structure. Successful candidates will be a minimum of 21 years of age, have extensive experience leading sea kayak trips. Current Wilderness First Responder (WFR) certification with CPR required.

Lead Instructors – *Land Based

    Instructors for land (or “island”), based expeditions are responsible for the physical and emotional safety of students throughout a 7 day course on Thompson Island, on a 24/7 basis. Course elements include camping, climbing and environmental exploration for single gender groups ages 12-14. An understanding of and sincere belief in the Outward Bound philosophy is essential to the position and to the overall success of this course. Instructors for our Island based courses are effective and compassionate leaders, familiar with the challenges that the 12-14 year old student faces and ability to help them find success at different levels. Our island based expeditions cater to a diverse group of students, aiming to help each achieve their own level of success with their Outward Bound experience. Current Wilderness First Responder (WFR) certification with CPR required.
    *Experience working with students who face such challenges as Anxiety, ADHD and Autism is also essential to this position. Lead instructors must possess all the skills and validated relevant experience necessary to lead a group in a wilderness setting, including demonstrated decision-making skill, self-care and pacing, and the ability to reach quantifiable objectives. Instructors must be able to demonstrate and teach camp craft and sustainability practices (LNT) and facilitate all daily activities required on course.

Assistant Instructors – Sailing, Kayaking or Land Based Expeditions

    This position requires the same maturity and skills as a Lead Instructor but allows space for a newer instructor, or someone new to Thompson Island, to become more comfortable with our course area and big picture group management. Assistant Instructors work in the field under the supervision of a Lead and may in turn be supervising and mentoring a second assist or an intern. Most assistant instructors work for at least one season before becoming a Lead. The Assistant Instructor position requires a minimum of Wilderness First Aid and CPR certification. Wilderness First Responder (WFR) preferred with a minimum Wilderness First Aid (WFA) certification and CPR required.


Watch Officers (Licensed Captains – Sailing Programs)
Coast Guard – Licensed Captains (Watch Officers), are required on every one of Thompson Island’s sailing expeditions. To be considered for the position, applicants must hold a current 50-ton (or greater) USCG issued License with sail endorsement that is valid for the duration of the upcoming season, a TWIC card, or ability to attain prior to season start and current medical certifications. Watch Officers are responsible for expedition route planning, sailing instruction, and the handling and care of our 30′ sprit-rigged pulling boats. We operate 7-12 day expeditions on the Boston Harbor, Mass Bay and up the Massachusetts coast line. Courses include co-ed environmental expeditions for students age 15-18, single gender expeditions, for students 12-14 and shorter week long expeditions for college students. A full slate of courses is scheduled for the summer season offering plenty of work. The work and the students can be challenging and unpredictable, requiring strong leadership skills and flexibility. But for the right person prove an extremely rewarding and unique experience. Thompson Island Outward Bound offers competitive salary and professional development for this position.

Course Directors
A Course Director (CD) is responsible for the overall quality, consistency and safety of the Outward Bound courses in their charge. In most cases Course Directors are seasoned Outward Bound instructors who have demonstrated an outstanding ability to supervise and train others. From pre-course planning to the student graduation ceremony and post-course debrief, the CD is the point of contact for instructor teams in the field and the families of the students on course. The CD is most often at base coordinating with other departments, islands or outside entities to ensure the courses in the field run safely and smoothly at every turn. Course Directors may go into the field multiple times throughout course to advise teams on situations requiring outside assistance or to resupply their crew(s). Course Directors should be at a level of skill with their course element wherein they could comfortably replace a Lead Instructor in the field if the need presented itself. 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. Thompson Island Outward Bound offers competitive salary, housing and professional development for this position. Wilderness First Responder (WFR) and CPR certification required.

Climbing Site Managers
Site Managers possess extensive knowledge of industry standard operating procedures for challenge course operations. Site Managers must be comfortable moving and working at height and must be physically capable of climbing challenge course elements. Site Managers are responsible for the setup and takedown of high challenge course elements as well as the overall management of the climbing site while in use. Site Managers demonstrate abilities and skills similar to that of the ACCT Level 2 Challenge Course Practitioner Certification. Documented Challenge Course hours may be a requirement for this position upon request. An ACCT, PRCA, or AMGA certification is a plus. Wilderness First Responder (WFR) and CPR certification required.

Curriculum Delivery Specialist
A curriculum delivery specialist (CDS) is responsible for delivering curriculum for the Thompson Island Outward Bound connections program. Working with students from rising 4th-8th grade, the person should be comfortable in front of groups of students teaching Experiential Environmental Science, Math or English Language Arts (ELA). This person will be responsible for delivering curriculum in BPS classrooms all over the Greater Boston area as well as on Thompson Island. Occasional overnight responsibilities for island curriculum delivery are expected as well. A degree in education or environmental science is not necessary, but strongly encouraged. Essential for this position is the ability to provide appropriate and timely feedback to the Program Director, Curriculum Programs to enhance current curriculum design. Opportunities exist for professional development in creating new lesson plans and modules based on organizational need. Ideally, this person will have had experience with Thompson Island, the Boston Public School system or the Boston Harbor Islands.

Outward Bound Professional Staff
The mission of Outward Bound Professional (OBP) is to create positive lasting change in the workplace. With this mission in mind, OBP facilitators provide cutting-edge, customized programs that enhance the effectiveness of individuals, groups, and organizations. OBP programs serve a diverse clientele from Northeast area businesses and organizations to Boston area colleges and universities. OBP Facilitators possess extensive knowledge of adult/business focused programming and group processing skills. Successful candidates have prior experience with facilitating problem solving initiatives, experiential learning models, and low and high challenge course elements. Prior experience or formal education in organizational behavior, business management, higher education, or experiential education is a plus. An ACCT Level 1 or 2 certification is also a plus.

Field Staff Employee Benefits

Thompson Island offers industry competitive pay along with rewarding work and opportunity for professional development in the field of experiential education.

Staff Trainings
Offered each season, our trainings include challenge course and group facilitation, student management and environmental initiatives and curriculum. Most training is program-specific and open only to current field staff, interns and pre-qualified applicants. Additional, more specialized trainings and opportunities are offered to certain positions in-line with the requirements of that position, its course area, and the program element. These include, but are not limited to: ACA Kayaking Certification, Sail Training, Challenge Course Safety Management, Corporate Group Facilitation as well as peer and mentor lead development opportunities throughout the season.

Seasonal staff can request housing on Thompson Island for the duration of their employment within a given season. Preference is given in accordance with length of commitment, requirements of the position being filled and under the contingencies of the Residential Housing Policy. The staff dorm on Thompson Island, which opens at the beginning of our spring season and closes at the end of the program season, offers 2-6 person rooms, a comfortable common area, full kitchen with hot/cold food storage and free laundry machines. Twice daily ferry service provides transportation between the island and the city of Boston at no cost to employees.

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Thompson Island Outward Bound Education Center