Course Facilitator

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 at THEARC in SE 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.

We’re hiring purpose-driven, growth-minded Day-Program Facilitators for our Baltimore City 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.

Location: Baltimore
Schedule: Part-time, seasonal (Spring–Fall)

Start Date: March 23, 2026

Compensation and Benefits: Per diem- $120.00 training; $144.00 after training

• Seven (7) days of Paid Sick Leave.
• Up to eight (8) 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:

• Room and basic Board, if you elect to live in CBOBS’ staff house
• Access to Pro-deals
• Discounted rates for Staff Invitationals at other Outward Bound bases during the off-season

• Facilitate 1-day programs primarily onsite at our Baltimore location, occasionally at our DC location, as well as occasional offsite programs at partner locations such as a school gymnasium. Group transportation using organization vehicles will be provided; personal mileage will not be reimbursed.
• 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, assist in daily reporting.

Minimum Qualifications

• 21+ years old
• Must clear a federal and state background check
• Adult CPR and First Aid, with Epi Pen 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,…