Camp Director, Waypoint Academy - $150,000/year USD

• On-site position at Waypoint Academy located in Dripping Springs, Texas
• $150,000 annual salary as a W2 employee with weekly pay. Health benefits begin on day one.
• Relocation assistance provided
  
  

The best way to support a young person is to give them something difficult and let them carry it themselves. If that statement unsettles you, this isn't the right role. If it resonates, read on.

Waypoint Academy runs core academics through self-guided, AI-driven adaptive platforms that condense traditional school hours into a concentrated morning session. No classroom lectures. This structure frees you to focus on the work that truly shifts outcomes for students. Your morning may begin with a one-on-one coaching conversation with a Guide, analyzing student performance data to identify where a group is falling behind. By midday, you're outside facilitating a hands-on workshop that builds teamwork and grit through authentic challenges. Afternoons are reserved for motivation work: sitting with individual students, understanding what motivates them, and helping a disengaged kid take ownership of their trajectory. You maintain your own student cohort throughout, keeping your coaching grounded in live practice rather than theory.

You've likely been the outlier in traditional education settings: too focused on outcomes, too comfortable with data, too ready to take students outdoors and let them face real struggle. This may be the first environment where that approach is valued. You begin coaching other Guides immediately, and as your results compound, the standard you establish influences the entire cohort and your role in shaping the program deepens. You'll witness the impact firsthand: a doubtful student who begins taking ownership, a Guide who improves because you gave them direct feedback, a young person who returns from a challenge visibly more capable.

Uphold the standard. Take them outside. Apply today.

What You Will Be Doing

• Provide coaching to the Guides you work with: analyze performance metrics, observe their interactions with students, and conclude each session with clear, actionable steps to improve.
• Facilitate one-hour outdoor workshops focused on life skills where K-12 students develop leadership, resilience, teamwork, and communication through adventure-based activities.
• Conduct motivation sessions leveraging student analytics and Coachbot insights to ensure every student advances toward their goals and takes responsibility for their progress.
• Maintain your own student cohort while mentoring other Guides, ensuring your coaching comes from active practice rather than past experience.
• Monitor student satisfaction, goal achievement, and Guide performance on a weekly basis to identify and address underperformance early.
  
  

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring. Students engage with self-guided adaptive platforms, frequently without direct adult supervision.
• Creating curriculum or designing lesson plans from the ground up. The frameworks are already in place; your focus is on execution and energy, not innovation.
• Training Guides on instructional methods. Since Guides don't lecture, you'll coach them on motivation, accountability, and presence with students.
• Compromising standards to avoid conflict. You won't advance a student prematurely or overlook underperformance in a Guide.
• Confining students to indoor, seated environments. A substantial portion of learning occurs outdoors through structured challenge.
  
  

Camp Director Key Responsibilities

Ensure every student in your cohort develops a love for school, demonstrates academic growth, and acquires the character and life skills necessary to succeed.

Basic Requirements

• Willing to work in person at Waypoint Academy in Dripping Springs, Texas
• Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or a related field
• At least 5 years in education, youth development, coaching, outdoor education, or learning and development (L&D)
• Track record of leading a team of 5 or more adults, including hiring and performance-based termination decisions
• Direct experience working with youth ages 5-18 in an educational or developmental setting
• Built, launched, or significantly grew a program, team, school, or outdoor initiative from the ground up, with a specific and measurable example
• Proven use of data and metrics to set goals and drive decisions, not just report results
• Legally authorized to work in the United States
  
  

Nice-to-have Requirements

• Master's degree in a related field
• Coached athletics, led wilderness or experiential programs, directed camps, or ran youth programs at a scale that required running cohorts and measuring outcomes
• Left classroom teaching to build or run programs from a different seat: EdTech, tutoring, youth nonprofits, or school intervention teams
• Early-career track record of high personal performance, academic, athletic, or professional, before moving into leadership
• Belief that the standard education model is broken and personal investment in rebuilding it
  
  

About Waypoint Academy

Nature-based school that blends rigorous academics with real-world challenges.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $75 USD/hour, which equates to $150,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5818-US-Dripping-CampDirector