Job Description

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.
###

Physical Abilities

This position requires physical agility and stamina. Walking, hiking, running, standing, lifting, and bending will be a routine part of this position. Employees will need to be able to keep visual cues on students and be able to hear them. Guides must be physically able to facilitate and lead students safely on adventures in various settings.
###

Compensation & Schedule

Pay rate is $25 per hour. Mileage reimbursement is the current IRS rate of .07 per mile.

This position will start ASAP, for the 25/26 school year.

This is a part-time position, 5 hours per week, with most of the hours taking place on Adventure Fridays during normal school hours. Most adventures are 2-5 hours in length. The majority of the job will be performed on Fridays. The typical time spent per week for the position will be under 5 hours.


We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.