Love Adventure and Variety? Become a Roaming Guide!
Are you energized by new people, flexible roles, and working outside? Do you love helping teens grow into confident leaders?
Williamsburg Learning is hiring part-time Roaming Guides to support our Adventures Program in Denver and Douglas County. Rather than being assigned to one group, you’ll float between local teams—stepping in where help is needed most and ensuring that every student gets a transformational experience.
About Williamsburg Learning
Williamsburg Learning is an educational services provider that partners with schools like Williamsburg Academy of Colorado and Leadership Academy of Utah to deliver online and in-person learning experiences that prepare students for meaningful lives as principled leaders.
We believe in classical education, personal growth, and human connection—and we bring those values to life through every Adventure.
Why This Role Exists
Our Outdoor Adventures course is an experiential PE class for students in grades 6–12, featuring hands-on activities like hiking, skiing, canoeing, snowshoeing, rock climbing, and survival skills. Meanwhile, our Leadership Adventures course develops students' leadership through museums, service projects, college visits, and group challenges.
Roaming Guides play a vital role in both programs by supporting multiple groups throughout the semester—bringing energy, structure, and leadership wherever it’s needed.
What You’ll Do
Assist with 15 adventure events per semester (mostly Fridays between 9 a.m.–3 p.m.)
Travel between Adventures groups within Denver and Douglas County
Support different groups based on need, including last-minute substitutions
Facilitate outdoor activities, group games, and leadership challenges
Guide students through meaningful 1:1 and group discussions
Help with setup, attendance, cleanup, and caring for gear
Ensure student safety in coordination with local Adventure Leads
Attend all required trainings (paid, online and in-person)
You’re a Great Fit If…
You’re energetic, adaptable, and love working with teens
You’re dependable, organized, and ready to lead in a flexible environment
You’re excited by variety and can jump into new groups with ease
You thrive outdoors—even in unexpected weather
You’re comfortable with light physical activity (e.g., hiking, lifting gear)
You care deeply about community, mentorship, and student growth
Core Values We Look For
Growth – You’re always learning and seeking personal/professional development
Right Action – You do the right thing, even when no one’s watching
Culture of Belonging – You bring your authentic self and help others feel welcome
Why Join Williamsburg Learning
This isn’t just part-time work—it’s purpose-driven leadership. You’ll be part of a team that believes in helping students become leaders through hands-on, human-centered learning. You’ll receive training in mentorship and facilitation, join a supportive culture, and grow alongside your students.
Great Benefits! PTO–Even for part time roles! Opportunities for growth! 4% 401K matching! Employee Growth Challenges! Employee Retreat!
The Details
Part-time, mostly Fridays during the school year, some trainings held over zoom on Thursdays.
15 adventure events per semester (Aug–Dec & Jan–May)
Paid trainings each semester (online)
Must be 18+ with valid driver’s license and CPR/First Aid cert (or willingness to obtain)
Local travel required within Denver/Douglas County (mileage reimbursed)
Physical activity involved (hiking, moving gear, etc.)
Ready to Apply?
If you're someone who shows up early, jumps in with confidence, and finds joy in helping students grow—you might be exactly who we're looking for.
Apply now with your resume and a cover letter explaining why this role + you = a match made in adventure heaven.
If you're someone who shows up early, jumps in with confidence, and finds joy in helping students grow—you might be exactly who we're looking for.
Apply now with your resume and a cover letter explaining why this role + you = a match made in adventure heaven.