The Program at the Chesapeake Bay Outward Bound School (CBOBS) strives to be the leading provider of experiential social-emotional learning in the Mid-Atlantic region. CBOBS offers single-day team building programs to a wide variety of participant groups, including but not limited to, public, private, and charter schools, colleges and universities, community organizations, religious groups, businesses, non-profit organizations, government agencies, and more. Facilitators work primarily with youth from Baltimore and DC schools. However, staff will also work with professional adult groups, educators, police officers, and more. An ideal candidate for the position will be competent in interacting and working with diverse populations.

Facilitators will spend most of their time engaged in direct programming which includes on-the-ground activities, as well as managing off-the-ground climbing elements. Staff will develop skills to competently facilitate team-building activities designed to build group relationships and teamwork, assertiveness and perseverance, physical confidence and self-regulation, and self-awareness and social responsibility.

Training is provided for the facilitation of both experiential social-emotional learning activities and technical climbing activities.

Essential Duties and Responsibilities

  • Show respect and compassion for others and create an emotionally safe environment for students and staff
  • Attend required staff trainings
  • Plan and facilitate the following activities with participants of different ages: high climbing elements, low elements, initiative activities, debriefing conversations, lessons, and outdoor activities
  • Adhere to all local operating procedures, safety policies and emergency procedures outlined in the staff handbook
  • May be required to manage a student group in emergencies as needed and as appropriate
  • Consistently strives to give and receive timely, honest feedback with co-workers and supervisors.
  • Commits to own professional growth as well as improving technical and interpersonal skills.

Minimum Qualifications

  • Must have all vaccines recommended by the CDC, including a COVID 19 vaccine, by the first date of employment or arrival on base.
  • Must be 21 years of age or older.
  • Ability to clear federal and state background checks.
  • Have exposure to and comfort with working outdoors in various weather conditions.
  • Must work well in a team environment and excel under pressure.
  • Adult CPR certification is required. WFA (Wilderness First Aid) or WFR (Wilderness First Responder) is preferred.
  • 40+ days of experience in education, coaching, youth engagement, group management, or teambuilding facilitation is strongly encouraged.

Compensation & Benefits

  • Pay rate for Day Program Facilitators begins as per-diem at $105 - $150/day (based on experience) with promotion opportunities after training and experience.
  • Housing and food staples are offered during work time.


  • The Day Program Facilitator position can be part-time seasonal or full-time seasonal. Programming primarily occurs from March – November; facilitators are hired seasonally.
  • Due to the seasonal nature of programming, work may be light or heavy at different times of the year.
  • Must be available on Mondays for program planning and preparation, and minimum 2 additional weekdays. Weekend programming is rare.
    Work hours are typically from 7:30 AM – 4:00 PM. Times may vary depending on the program partner and location.
  • Work hours are Monday - Friday with occasional weekends
  • Programs occur both on-site at CBOBS’ facilities located in the 1,216-acre Gwynns Falls Leakin Park in Baltimore, MD as well as various off-site locations including Marvin Gaye Recreation Center, Palisades Recreation Center, and Fort Lincoln Park in Washington DC, and sometimes in the gymnasiums, classrooms, or outdoor fields of our school partners.

To Apply

Please complete the online application or submit your resume and cover letter via email to Rice Ermilio, People & Culture Coordinator, at

The Chesapeake Bay Outward Bound School is an EEO/ADA employer. Chesapeake Bay Outward Bound School prohibits discrimination against any student or applicant because of race, color, religion, sex, gender, ethnic or national origin, sexual orientation, qualified individuals with disabilities on the basis of disability, or any other category which may be protected by applicable state or federal law. Chesapeake Bay Outward Bound School also promotes respect for all people and will not tolerate harassment based on any of these characteristics nor on differences based on gender identity or expression.