What are the responsibilities and job description for the Camp Director, Waypoint Academy - $150,000/year USD position at Crossover?
- Based on-site at Waypoint Academy, Dripping Springs, Texas
- $150,000 annual salary as a W2 employee, with weekly pay. Health benefits begin on day one.
- Relocation assistance provided
Waypoint Academy operates with core academics delivered through self-guided, AI-powered adaptive applications that condense the traditional school day into a concentrated morning block. There are no lectures. This structure frees you to focus on the work that genuinely shifts a student's path. A typical morning may begin with a one-on-one coaching conversation with a Guide, analyzing student performance data to identify where a cohort is losing ground. By midday, you're outside facilitating a workshop that builds teamwork and resilience through hands-on challenge. Afternoons are reserved for motivation work: one-on-one sessions with students to uncover what drives them and to move a disengaged student toward meaningful goals. You maintain your own cohort throughout, ensuring you stay current on the very skills you're coaching others to develop.
You've likely been the outlier in traditional education—too metric-focused, too outcome-oriented, too comfortable taking students outside and letting them wrestle with difficulty. This may be the first environment where you belong. You begin coaching other Guides immediately, and as you produce results, the standard you establish influences the entire cohort and your authority over the program expands. You'll witness the impact firsthand: a doubtful student who begins to take ownership of their growth, a Guide who sharpens because you gave them direct feedback, a young person who emerges from the wilderness more capable than when they entered.
Uphold the standard. Lead them outdoors. Apply now.
What You Will Be Doing
- Provide coaching to the Guides on your team: analyze performance metrics, observe their interactions with students, and conclude each session with clear, actionable steps to address performance gaps.
- 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 informed by student analytics and Coachbot data 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 is grounded in active practice rather than past experience.
- Monitor student satisfaction, goal achievement, and Guide performance on a weekly basis to identify and address underperformance early.
- Delivering lectures or tutoring students in academic content. Students engage with self-guided adaptive applications, frequently with no adult present.
- Designing curriculum or lesson plans from the ground up. Existing playbooks are in place; success depends on execution and energy, not creativity.
- Training Guides on instructional methods. Guides do not lecture, so your coaching centers on motivation, accountability, and their presence with students.
- Compromising standards to maintain harmony. You will not advance a student prematurely or overlook a Guide's poor performance.
- Confining students indoors or to seated activities. A significant portion of learning here occurs outside, through challenge-based experiences.
Ensure every student in your cohort develops a genuine love for school, achieves academic growth, and builds the character and life skills necessary to succeed.
Basic Requirements
- Able to work on-site at Waypoint Academy in Dripping Springs, Texas
- Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or related discipline
- Minimum 5 years of experience in education, youth development, coaching, outdoor education, or learning and development (L&D)
- Demonstrated history of leading a team of 5 or more adults, including responsibility for hiring and performance-based terminations
- Hands-on experience working with youth aged 5-18 in an educational or developmental context
- Experience building, launching, or substantially growing a program, team, school, or outdoor initiative from inception, with a concrete and measurable outcome
- Established record of using data and metrics to establish goals and inform decisions, beyond simply reporting outcomes
- Legal authorization to work in the United States
- Master's degree in a relevant discipline
- Experience coaching athletics, leading wilderness or experiential programs, directing camps, or managing youth programs at scale with cohort management and outcome measurement
- Transitioned out of classroom teaching to build or lead programs in a different capacity: EdTech, tutoring, youth nonprofits, or school intervention initiatives
- Strong early-career record of individual achievement—academic, athletic, or professional—prior to entering leadership roles
- Conviction that traditional education models are failing and personal commitment to reimagining them
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-RoundRoc-CampDirector.001
Salary : $150,000