Location: Baltimore, MD
Reports to: Assigned Program Manager
Schedule: Variable over 9 mos
Status: 9-month position with 12-month benefits, full-time/ exempt


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.

For more information, please visit www.outwardboundchesapeake.org.


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.

Chesapeake Outward Bound School is currently hiring Instructors to lead wilderness expeditions and high-ropes challenge course programs. The most attractive candidates are skilled in both and have a desire to work where needed. The Instructor position is a 9-month position with 12-month benefits. This position works an average of 18 days a month, and no more than 162 days per 9 months, with at least 48 hours off guaranteed after any period of work lasting 15 straight days. Outward Bound includes ongoing professional development opportunities, position-specific training, and the option for community housing and basic board for apprentices, instructors, and instructors.

Key Competencies

Instruction / Facilitation / Character

  • Previous experience in facilitating group dynamics is desired, especially experience working with adolescents.
  • Communication skills, including active listening, giving and receiving feedback, and conveying expectations, are important skills for Instructors.
  • Ability to learn and adopt all safety policies and actively participate in risk management while instructing
  • Passion, confidence, and humor are vital to the success of our staff.

Outdoor Technical Skills

Outward Bound delivers programming through a variety of unique technical skills and diverse course areas. CBOBS is seeking Instructors with skills in these areas:

  • High-ropes Challenge Course
  • Sea Kayaking
  • Canoeing
  • Backpacking
  • Rock climbing

Competence in one or more of these areas is required for an Instructor position. A general comfort in the outdoors and remote areas is also required for all wilderness Instructor positions. Most importantly, we are looking to build on a foundation in outdoor judgment: the ability to make safe decisions under challenging circumstances. Applicants without technical skills but the desire to work as an Instructor should apply to our apprenticeship program.


As an Instructor promotes to a Lead 1 or above, the role will include leadership opportunities like facilitating trainings and mentoring incoming or junior staff.

Physical and Emotional Stamina

Applicants must be sufficiently fit to participate in all the course activities for a given course area and maintain energy, strength, and focus on assisting students with physical and emotional obstacles.

Other Duties as Assigned

This job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required for this role. Duties, responsibilities, and activities may change, or new ones may be assigned based on the need of Chesapeake Bay Outward Bound School.

General Requirements

  • 21 years or older
  • Current Wilderness First Responder (WFR) certification preferred. Adult CPR required.
  • Must have all vaccines recommended by the CDC, including a COVID 19 vaccine.
  • Must successfully pass a State of Maryland and an FBI Criminal Background Check and a driving record check.


Lead level and compensation are determined by the interpersonal, professional, and technical skills an individual has when applying. Salary increases are possible on an annual basis and are determined in the same way.

Lead 3$36,000/year
Lead 2$30,000/year
Lead 1$25,000/year


  • Employer contribution of 75% for Medical, Dental, & Vision insurance through CareFirst BlueChoice for the employee and their children, if applicable.
  • Five (5) days of Sick Leave (PTO).
  • Eight (8) weeks of paid Family/Medical leave
  • 401(k) with a match. Employees are eligible for participation after 1 year of employment. The current match is 6% of the employee’s salary.
  • Long-term disability, short-term disability, AD&D insurance, and a $25,000 life insurance policy at no cost to the employee.
  • Pre-tax Saving Cafeteria Plan: Healthcare Flexible Spending Account (FSA), Dependent Care Flexible Spending Account (FSA), Health Savings Account (HSA).
  • Pre-tax Commuter/Transit Benefits.
  • Employee Assistance Program (EAP).
  • Aflac Supplemental Insurance.
  • Pro Deals: Discounts from outdoor industry vendors for outdoor professionals.

To Apply

Please send cover letter and resume to Megan Campbell, Program and Safety Director at jobs@outwardboundchesapeake.org. Applicant review will begin immediately and be ongoing.

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.