As leaders in the wilderness-based experiential education field, we look to hire staff that, first and foremost, have a strong desire to educate youth.

Open Positions:



Our office crew works with the field staff to deliver strong, meaningful programs. We hire flexible, motivated, self-reliant people to create an administrative team which is focused on mission delivery.

Open Positions:

Executive Assistant

Development Director

Our Culture

Outward Bound is an international educational movement dedicated to the idea that people are capable of far more than they know. Originally designed for young sailors during World War II, the program fostered leadership qualities needed to head out on the high seas- when ships were “Outward Bound.” Now, all around the world, Outward Bound schools prepare people to take on challenges and achieve more than they ever thought possible.

Our employees are the heart and soul of our organization. Whether you’re leading a group on a wilderness expedition, working with urban youth in their community or creating a feeling of adventure in the classroom, your job is to help students see the possibility in themselves and the world around them. Outward Bound employees inspire, serve and lead. We believe we are in the business of helping to create a better world. Whether you work directly with students or behind the scenes in an office, everything we do touches the student experience. Those passionate for exploration and education should apply.

Outward Bound is a wonderful place to work. The work is powerful; the challenges are real. You may be raising money or climbing a peak, but you will need to give it your best. We excel at building communities — in the workplace, at our basecamps, on our courses. Employees are dedicated and committed, but we still know how to have fun.

As an organization, we strive to offer the same excellence to our staff that we do to our students. Integrity and compassion are part of our values. We aim to create a supportive environment and serve our employees well. Collaboration, effective problem solving and creativity are important components in our work life at Outward Bound. Outward Bound is an equal opportunity provider and 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.

What it takes to be an Outward Bound Instructor

As leaders in the wilderness based experiential education field, we look to hire staff that have a strong desire to educate youth. Our staff are mission-driven, tight-knit, diverse and inclusive. Our staff members come from varied backgrounds; they are traditional classroom educators, wilderness educators, outdoor enthusiasts, veterans and much more. They are folks who have sought out a work life that is inspiring, impactful, challenging and fun.

The populations we work with are just as varied as our staff. The under-served youth of Baltimore makes up the greatest segment of our student population. Field staff must have a strong will and desire to deliver our mission to those who could benefit most from it. We also serve students who come from all over the country, youth who have risen to leadership roles in their schools, on sports teams, and within other community organizations. We serve veterans, large corporations, kids as young as 10 and adults of all ages.

Applicants who demonstrate professionalism, commitment, and interpersonal competence will be extremely successful. Outward Bound field staff are also flexible, humble and open-minded leaders. They seek out opportunities for growth, are able to give and receive feedback and demonstrate strong communication skills. They display proven and sound judgment in challenging circumstances but also the ability to learn from mistakes. Our community and culture is centered around humility, self-awareness, sense of humor and above all, compassion.

We deliver our mission on High Ropes courses, backpacking on the Appalachian Trail, canoeing on the Delaware Water Gap and Potomac River and traversing the cities of Baltimore and Philadelphia. Applicants who have technical skills as both a backpacker and as a paddler will be highly competitive. That said, a proven and sustained ability to work with underserved populations in an urban setting is of utmost importance. As you can imagine, individuals who encompass these skills are the most desirable candidates for field staff positions.

We hire many field staff positions yearly. These can include:

  • Apprentices
  • Logistician
  • Assistant Instructor
  • High Ropes Facilitator
  • Course Director

As positions become available job descriptions will be posted to this website under the “Jobs” tab.
General Qualifications for Field Staff (dependent and varied based on position)

  • Wilderness First Responder or Wilderness First Aid certified
  • Ability to carry 40-50 lb. backpack both on and off trail for extended periods of time, often up to 10-12 hours a day
  • Competency with map and compass navigation
  • Comfort with backcountry living; cooking, camping, Leave No Trace, etc.
  • Personal experience with extended expeditionary travel
  • Comfortable with basic paddling skills; American Canoe Association Certification and/or Wilderness Lifeguard Certification is considered a plus
  • Capable on high ropes courses
  • Strong facilitation and communication skills

General Requirements for Field Staff

  • Interns must be 18 years old
  • Instructors and Logistics staff must be 21 years old
  • Clean driving record
  • Excellent physical condition
  • Background clearance including the following must be provided before employment is offered:
    • FBI and Maryland criminal clearance via fingerprints
    • Pennsylvania criminal clearance
    • Pennsylvania Child Abuse Clearance