The Insight Program at the Outward Bound Baltimore Chesapeake Bay School (CBOBS) strives to be the leading provider of character education in the Mid-Atlantic region. CBOBS offers day-long team building programs to intact groups of participants (i.e. schools, community organizations, companies, religious groups, etc.). Participants vary dramatically. The CBOBS Insight team focuses primarily on youth from Baltimore schools. However, the staff will also work with adults, teachers, police officers, and companies. An ideal candidate for the position will be competent in working with a variety of participants.

The Insight team will spend their days engaged in activities that foster collaborative problem-solving, constructive communication, a supportive environment, and stepping out of comfort zones. An Insight Instructor has the ability to competently facilitate ground games and initiatives, derive learning from experience, as well as an ability to safely manage and facilitate high-ropes elements.

Essential Duties and Responsibilities

  • Participates in required staff training
  • Assist in the design and facilitation of Insight programs as contracted with the client and in line with Outward Bound educational framework, philosophy, mission and processes
  • Assess students to ensure all activities are appropriate for demonstrated experience level and desired group outcomes
  • Lead and facilitate the following activities with students of different ages: High Ropes, Low Ropes, Initiative Games, Debriefing Conversations, and Outdoor Activities
  • Demonstrates multicultural competence and sensitivity
  • Demonstrate an on-going desire to work with Urban students in the outdoors
  • Effectively recognize and address issues of diversity as appropriate
  • Effectively assist co-facilitators or Course Director when discussions regarding diversity are called for
  • Show respect and compassion for others and create an emotionally safe environment for students and staff
  • Clearly establish limits and boundaries for student behavior and independence
  • May be required to manage a student group in emergencies as needed and as appropriate
  • Teaches and shares information with coworkers and students in a coherent and engaging manner
  • Consistently strives to give and receive feedback with coworkers and supervisor
  • Demonstrates the ability to behave as a role model for students
  • Actively seek out opportunities to give and receive performance based feedback
  • Initiate and commit to own professional development; technical and interpersonal
  • Under the supervision of the Course Director or Program Director, perform regular maintenance checks on ropes course, equipment and gear in order to maintain safety and integrity
  • Adheres to all local operating procedures, safety policies and emergency procedures outlined in the staff handbook
  • Is able to locate and use communication systems in the event of an emergency
  • Other duties as assigned

Knowledge and Skills

  • Possess knowledge of own strengths, limitations and needs along with the willingness to seek constant improvement
  • 40+ days of high ropes experience strongly encouraged
  • 40+ days of group management and facilitation strongly encouraged
  • Experienced in working with a range of participant populations
  • Demonstrates proven competencies in managing challenging groups of students
  • Able to recognize when issues of inclusion and/or safety need to be addressed
  • Is able to articulate the Outward Bound mission
  • Possesses and implements tools to manage personal stress while on the job
  • Maintain a minimum CPR certification; WFA (Wilderness First Aid) preferred
  • Have knowledge of and adhere to (COPPs) Charter Operating Policies and Procedures, safety procedures, and (ERP) Emergency Response Plan

Compensation & Benefits

  • Paid based on the Outward Bound credit scale at a per-diem Facilitator pay level
  • Housing and food staples offered during work time
  • The facilitator position is part-time, hired seasonally March – November


The Insight program is a flexible schedule. Work may be light or heavy at times. Facilitation days may range from 1 to 4 days per week. Days of facilitation typically begin at 7:30 AM and conclude by 4:00 PM.

To Apply

Please submit resume and cover letter via email to Rice Ermilio, People & Culture Coordinator, at

The Chesapeake Bay Outward Bound School is an EEO/ADA employer