Founded in 1986, Chesapeake Bay Outward Bound School’s (CBOBS) mission is to change lives through challenge and discovery. Outward Bound is an international educational movement dedicated to the idea that people are capable of far more than they know. CBOBS is committed to providing transformational experiences to a diverse group of youth and adults through one-day programs, virtual programs, and multi-day expeditions. CBOBS operates programs in Baltimore City, the Appalachian Trail in MD and PA, the Potomac River, the Dolly Sods Wilderness Area in WV, and the Eastern Shore of the Chesapeake Bay. CBOBS’ facilities are in Leakin Park in Baltimore City.

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Instructors are the cornerstone of our programming. They are responsible for the successful execution of all program types. Instructors work directly with a wide range of program participants. Senior Instructors will also support junior Instructors through leadership and mentoring. An Instructor’s work will range from facilitation to program support, including occasional on-call duty and administrative tasks. Instructors at Outward Bound are expected to learn OB’s curriculum and design courses to meet the needs of our students. Understanding of and commitment to the Outward Bound philosophy and curriculum are keys to success for this position. The ideal Instructor is an adaptable, creative, and compassionate educator.

Outward Bound field staff are trained to identify, assess, and approach risk as a learning tool to be managed, but not eliminated, to provide Outward Bound students with the opportunity to gain insights and perspectives into their own and their group’s capabilities are unavailable anywhere else.

General Requirements

  • Cleared federal and state background check
  • Sufficient physical fitness to perform the job
  • Successful completion of 10-week apprenticeship program or equivalent experience

Core Competencies

Leadership – This competency includes demonstrating the knowledges, skills, and abilities of a leader and the ability to teach students and peers leadership skills.

  • Is familiar with leadership models and can assess their own style of leadership in most situations
  • Is a positive role model for students in demeanor, language, and reactions and responses.
  • Active observer of Lead staff and effective collaborator with Lead staff
  • Shows respect for different experiences and perspectives
  • Teaches and practices communication skills, giving and receiving feedback, and active listening
  • Teaches tools for decision making, goal setting and goal achievement.
  • Demonstrates good leadership presence, approachability, humility, and honesty to peers and students

Outward Bound Mission Delivery – This competency includes application of OB philosophy and Educational Framework as well as ability to deliver stated course outcomes.

  • Relates OB mission, history and values to students
  • Can recognize and implement Domains of Thriving best practices
  • Understands and articulates intended program outcomes
  • Selects lessons and guides discussions that support program outcomes

Education – This competency includes skills, knowledge, and ability to craft and follow curriculum, to teach and present, and to educate others.

  • Assumes role of teaching, role-modeling, and/or coaching as appropriate
  • Delivers lessons, games, or initiatives which will be engaging and effective at delivering course ▪ outcomes
  • Presents information in a coherent way that can meet a variety of learning styles
  • Considers group/individual student assessment and needs when selecting program activities

Technical / Outdoor Skills – This competency includes all acquired/assessed technical skills and general comfortability on programs in all environments and weather types.

  • Teaches and role models good self-care: hygiene, hydration, sun protection and nutrition
  • Teaches and role models Leave No Trace principles and ethics
  • Can inspect, maintain, and repair equipment as necessary
  • Personal equipment-system is reliable, organized, and in good repair
  • Gaining proficiency in backpack, canoe, sea kayak and belay-monitor skills through the BCBOBS training and assessment process

Student Management – This competency includes the ability to create and maintain rapport, respect for all, student equity and voice, and a positive group culture.

  • Actively builds rapport and positive group culture through motivating, tone-setting, and introducing interpersonal skills like circle-ups, ‘talking stick’, and other group process structures
  • Can be firm and will engage to correct and address negative student behaviors
  • Addresses overt and covert inappropriate language, discrimination, and harassment
  • Can teach and explain conflict resolution tools: Ownerships, CFR, VOMP
  • Aware of other life skills lessons and theories regarding anger management, choice theory, and trauma-informed care

Safety Management – This competency includes risk assessment, knowledge of / adherence to policy / procedure, incident reporting / analysis, judgment, and decision making.

  • Knows and adheres to policies and procedures
  • Exhibits sound judgment and activity management
  • Identifies potentially dangerous situations pro-actively and makes decisions to avoid unnecessary risks ▪ Can locate and use field communication technology and call-sheets in the event of an emergency

Additional Responsibilities

Approach to Work / Professionalism – This responsibility includes communication skills, ability to work with others, timeliness, appearance, flexibility, and the quality of work.

  • Adheres to standards set in Employee Handbook
  • Communicates and coordinates appropriately with supervisors and co-workers as needed
  • Approaches new information with a desire to learn
  • Receptive and responsive to feedback from co-workers
  • Constructively addresses interpersonal issues within instructional team
  • Sets relevant goals and gives honest self-feedback
  • Dresses appropriately for audience and program type
  • Is on time and prepared for all work assignments

Community Impact – This responsibility includes adherence to CBOBS community standards / rules, and their impact / level of engagement in the BCBOBS community.

  • Adheres to and follows all basecamp and staff-house policies, rules, and standards
  • Contributes to a positive staff-community
  • Eager to gain knowledge about the students and community that BCBOBS serves


Part-Time, Per Diem staff are paid at a rate of $90/day and $70/training day.

To Apply

Please send cover letter and resume to Megan Campbell, Program and Safety Director at

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.