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

• On-site position at Waypoint Academy, Dripping Springs, Texas
• W2 compensation of $150,000 annually, with weekly pay. Full health benefits from day one.
• Relocation assistance provided

The greatest gift you can give a young person is a difficult task—and the expectation that they'll carry it themselves. If that statement unsettles you, this role isn't for you. If it resonates, read on.

Waypoint Academy runs its core academics on self-paced, AI-driven adaptive platforms that condense classroom time into a focused morning block. No traditional instruction. That structure frees you to focus on the work that actually shifts a student's trajectory. Your mornings might begin with a one-on-one debrief with a Guide, analyzing student data to pinpoint where a group is struggling. By midday, you're outside running a workshop that builds teamwork and grit through tangible challenges. Afternoons are reserved for motivation work: sitting down with individual students, identifying what drives them, and moving the reluctant ones toward ownership of their goals. You maintain your own student cohort throughout, ensuring the skills you coach remain grounded in current practice.

You've likely been the outlier in education—too metric-focused, too outcome-oriented, too comfortable taking students outdoors and letting them wrestle with difficulty. This may be the first environment that aligns with how you work. You begin coaching other Guides immediately, and as your results compound, the standards you establish influence the entire cohort and expand your impact on the program. You'll witness the results firsthand: a skeptical student who begins to take ownership, a Guide who sharpens because you gave honest feedback, a young person who returns from the field more capable than when they left.

Uphold the standard. Take them outside. Submit your application.

What You Will Be Doing

• Provide direct coaching to Guides on your team: analyze performance metrics, observe their work with students, and conclude each session with targeted actions that address performance gaps.
• Facilitate one-hour outdoor workshops focused on life skills, where students in grades K-12 develop leadership, grit, collaboration, and communication through experiential challenges.
• Conduct motivation sessions informed by student analytics and Coachbot insights to ensure every student advances toward their goals and takes ownership of their development.
• Maintain your own active student cohort while guiding other team members, ensuring your coaching is rooted in present experience rather than past recollection.
• Monitor student satisfaction, goal attainment, and Guide effectiveness on a weekly basis to identify and address underperformance before it escalates.

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring. Students progress through self-directed adaptive software, frequently without direct adult supervision.
• Creating original curriculum or instructional plans. Established playbooks are in place; success is defined by consistent execution and energy, not innovation.
• Training Guides on instructional methods. Since Guides don't lecture, your coaching centers on motivation, accountability, and presence with students.
• Compromising standards to avoid conflict. You will not advance a student prematurely or overlook a Guide's subpar performance.
• Confining students indoors. A substantial portion of learning at Waypoint occurs outside, through challenge-based experiences.

Camp Director Key Responsibilities Ensure that every student in your cohort is engaged and enthusiastic about school, demonstrates academic growth, and develops the character and life skills necessary for long-term success.

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 a related discipline
• Minimum of 5 years of experience in education, youth development, coaching, outdoor education, or learning and development (L&D)
• Demonstrated history of managing a team of at least 5 adults, including responsibility for hiring and performance-related termination decisions
• Hands-on experience working with youth between the ages of 5 and 18 in an educational or developmental capacity
• Experience building, launching, or meaningfully scaling a program, team, school, or outdoor initiative from inception, with a concrete and quantifiable example
• Documented use of data and metrics to establish objectives and inform decisions, not solely for reporting purposes
• Legal authorization to work in the United States

Nice-to-have Requirements

• Master's degree in a relevant field
• Experience coaching athletics, leading wilderness or experiential education programs, directing camp operations, or managing youth programs at a scale requiring cohort management and outcome measurement
• Transitioned out of classroom teaching to design or lead programs in another capacity: EdTech, tutoring organizations, youth-focused nonprofits, or school intervention initiatives
• Strong personal performance early in your career—academically, athletically, or professionally—prior to transitioning into leadership roles
• Conviction that traditional education models are inadequate and a personal commitment to reimagining them

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.004