Challenge Course Facilitator-Baltimore

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 Baltimores 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 theyre capable of and how they want to show up for others as teammates leaders and members of their community.

What Were Looking For

Were hiring purpose-driven growth-minded Day-Program Facilitators for our Baltimore City team. Youll 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.

Youll 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 youll feel at home here. Youll 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 (SpringFall)

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 employees 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

What Youll Do

• 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.

What Youll 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 1218) 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 drivers 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 (MarchNovember preferred)
• You grow as a facilitator teammate and changemaker

What Makes This Role Exciting

This is not just a job - its a journey of personal transformation just like the ones youll 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 youll 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.

Were 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 - wed 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 . 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 1025 lb packs supervising students for up to 7 hours and working outdoors in varied weather.