Work That Changes Lives - Empower students, explore nature, and grow as an educator and leader.

About Us

At Chesapeake Bay Outward Bound School (CBOBS), we believe every young person is capable of more than they know. Through immersive outdoor experiences, we help youth develop the courage, character, and leadership to thrive in school, in their communities, and for life.

Located in Baltimore’s Leakin Park and our new location at THEARC in Ward 8 of Washington, DC, we serve thousands of students each year from diverse communities by facilitating powerful learning moments in nature. As part of the Outward Bound USA network, we offer transformative experiences through backpacking, canoeing, Challenge Course, and team-building that center on social-emotional learning and equity-driven education.

The Challenge Course Facilitator job is about much more than teaching youth how to climb. This work is about helping students discover more about who they are, what they’re capable of, and how they want to show up for others as teammates, leaders, and members of their community.

Location: Washington, DC
Schedule: Part-time, Wednesday - Friday, seasonal (Aug-Nov)
Start Date: August 26, 2026

Compensation and Benefits:  Day Rate- $147.20 training; $159.60 after training  

• Seven (7) days of Paid Sick Leave.

• Up to twelve (12) weeks of paid Family/Medical leave

• 401(k) with a match. Employees are eligible for participation after 6 months of employment. The current match is 3% of the employee’s pay.

• Pre-tax Commuter/Transit Benefits.

• Employee Assistance Program (EAP).

Other Perks:

• Access to Pro-deals

• Discounted rates for Staff Invitationals at other Outward Bound bases during the off-season

What We’re Looking For

We’re hiring purpose-driven, growth-minded Challenge Course Facilitators for our Washington, DC team. You’ll lead 1-day Challenge Course and team-building programs, guiding students through purposeful activities, centered around predetermined outcomes, and guiding reflective discussions to drive transference of learning beyond our programming. 

You’ll help students build social emotional skills like teamwork and collaboration, perseverance and assertiveness, physical confidence and self-regulation, social responsibility and self-awareness. If you thrive in a close staff community and are energized by coaching youth through real-world learning, you’ll feel at home here. You’ll support students through physical, emotional, and social demands and help them turn new experiences into a sense of belonging, trust, self-efficacy, and more.

Requirements

What You’ll Do

• Facilitate 1-day programs primarily based at our Washington, DC, location, with additional opportunities at our Baltimore site and occasional offsite partner locations such as school gymnasiums. 

• Program activities focus on team-building experiences, both on the ground and on our challenge course.

• Design and adapt curriculum and lesson plans toward clear outcomes: Belonging, Courage, Physical Engagement, and Reflection. Craft daily progressions, reflection prompts, and debriefs to those outcomes, adjusting for student needs and partner goals.

• Use various education strategies to facilitate learning through experiential activities, many of which are challenging - physically, emotionally, or socially. 

• Build and maintain a positive and inclusive group culture, assessing group dynamics and using various student management tools to shape their experience.

• Manage the physical and emotional safety of all participants and staff and make proactive decisions to avoid unnecessary risk

• Follow CBOBS policies and procedures, elevate challenges to supervisors, report incidents in a timely manner, and assist in daily reporting.

• IMPORTANT NOTE: Regular travel between our DC and Baltimore locations will be required for approximately the first four months. While overnight stays are not expected, there may be consecutive days spent in Baltimore for shadowing, training, or workshop weeks. Lodging at our Baltimore staff house can be arranged as needed. Group transportation using organization vehicles will be provided; personal mileage will not be reimbursed.

What You’ll Bring

Minimum Qualifications

• 21+ years old

• Must clear a federal and state background check

• Adult CPR and First Aid, with EpiPen training (must be completed before training period ends)

• Experience with youth (ages 12–18) in schools, mentoring, camps, or community programs.

• Comfort with being outdoors, regardless of the weather, for a full program day

• Commitment to equity, inclusion, and working with diverse populations

• Able to support movement on uneven terrain, set up/operate Challenge Course elements, and manage safety systems (with or without reasonable accommodation).

• Valid driver’s license with insurable driving record (preferred, not required)

What Success Looks Like

• Students report positive growth in program outcomes: Belonging, Courage, Physical Engagement, and Reflection.

• You build meaningful, trust-based relationships between students and peers

• You demonstrate resilience, flexibility, and reflection, modeling self-regulation, and follow through

• You commit to and complete at least one full season (August–November)

• You grow as a facilitator, teammate, and changemaker

What Makes This Role Exciting

This is not just a job - it’s a journey of personal transformation, just like the ones you’ll lead students through. You will:

• Make real-time impact: Enable students to build courage, empathy, and deepen relationships among peers, one challenge at a time.

• Grow alongside others: Join a tight-knit, passionate community that values learning, feedback, and purpose.

• Gain professional tools: Facilitation, trauma-informed care, group management, and emotional intelligence - all transferable to future careers in education, counseling, or social impact.

• Step into purposeful growth:  If you enjoy pushing yourself to the edge of your comfort zone - emotionally, physically, and professionally - and believe people grow through challenges, you’ll feel at home here.

This work can include long days and often calls for flexibility, creativity, and quick thinking when plans change. We design experiences to be demanding for growth, and we prepare you to lead them well - with training, mentoring, clear safety systems, and a supportive team. Our aim is to set honest expectations, provide the tools to succeed, and recognize your impact.

Diversity, Equity, and Belonging at CBOBS

Chesapeake Bay Outward Bound School serves students across the DMV - Baltimore, Washington, D.C., and communities throughout Maryland and Northern Virginia. We believe every participant deserves access to safe, challenging, and joyful outdoor learning close to home.

We’re building a team that reflects the populations of the communities we serve. We welcome candidates of all backgrounds, identities, and lived experiences, including multilingual staff and educators with deep ties to Baltimore and D.C. communities. If you share our commitment to equity, inclusion, and belonging - and to helping students grow courage, confidence, and compassion - we’d love to hear from you!

ADA & Reasonable Accommodation

CBOBS provides equal employment opportunities and will consider reasonable accommodations for qualified applicants and employees. If you need an accommodation for the application or interview process, or to perform the essential duties of this role, please contact jobs@outwardboundchesapeake.org. Requests are reviewed on a case-by-case basis, consistent with the ADA and applicable law. 

Essential functions (with or without reasonable accommodation) include walking/hiking on uneven terrain, carrying 10-25 lb packs, supervising students for up to 7 hours, and working outdoors in varied weather.