Outdoor Education Director, Waypoint Academy - $150,000/year USD

About the Role

Waypoint Academy delivers core academics through self-directed, AI-driven adaptive platforms that condense the traditional school day into a concentrated morning block. No classroom lectures. That structure creates space for the work that genuinely shifts a student's path. Your morning may begin with a one-on-one coaching conversation with a Guide, analyzing student performance data to identify where a group is faltering. By midday you're outside, facilitating a workshop that builds teamwork and grit through authentic challenge. Afternoons turn to motivation work: meeting with individual students, discovering what compels them, and moving a disengaged kid toward meaningful goals. You maintain your own student cohort throughout, ensuring the skills you coach remain grounded in daily practice.

You've likely been the outlier in traditional education: overly analytical, excessively outcome-oriented, too inclined to take students outdoors and allow them to wrestle with difficulty. This may be the first environment designed for you. You begin coaching Guides immediately, and as you produce outcomes, the benchmark you establish spreads across the entire cohort and your authority over the program expands. You witness the impact directly: a doubtful student who begins taking ownership of their trajectory, a Guide who sharpens because you delivered honest feedback, a young person who emerges from the wilderness more self-reliant than when they entered. Maintain the standard. Lead them outdoors.

What You Will Be Doing

• Coach Guides working with you: analyze performance metrics, observe their student interactions, and conclude each session with concrete actions that address performance gaps.
• Facilitate one-hour outdoor life-skill workshops where students in grades K-12 develop leadership, grit, teamwork, and communication via adventure-based challenges.
• Conduct motivation sessions leveraging student analytics and Coachbot data to ensure every student progresses toward goals and takes ownership of their development.
• Maintain your own student cohort while mentoring other Guides, ensuring your coaching stems from active practice rather than past experience.
• Monitor student satisfaction, goal attainment, and Guide performance on a weekly basis to identify underperformance early.

What You Won't Be Doing

• Delivering lectures or providing academic tutoring. Students advance through self-directed adaptive applications, frequently without adult supervision.
• Creating curriculum or lesson plans from the ground up. The frameworks are established; your focus is execution fidelity and intensity, not innovation.
• Training Guides in instructional methods. Guides do not lecture, so your coaching addresses motivation, accountability, and presence with students.
• Compromising standards to avoid conflict. You will not advance a student prematurely or ignore a Guide's inadequate performance.
• Confining students indoors and seated. A significant portion of learning at Waypoint occurs outside, through challenge-based experiences.

Outdoor Education Director Key Responsibilities

• Ensure every student in your cohort is enthusiastic about school, demonstrates academic growth, and develops the character and practical skills necessary to succeed.

Basic Requirements

• Willing 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 termination
• Hands-on experience working with youth aged 5-18 in an educational or developmental context
• Experience building, launching, or substantially expanding a program, team, school, or outdoor initiative from inception, supported by a concrete and quantifiable example
• Documented use of data and metrics to establish goals and inform decisions, beyond simple reporting
• Legal authorization to work in the United States

Nice-to-have Requirements

• Master's degree in a relevant field
• Background coaching athletics, directing wilderness or experiential programs, managing camps, or overseeing youth programs at a scale requiring cohort management and outcome measurement
• Transitioned from classroom teaching to program development or leadership in EdTech, tutoring organizations, youth nonprofits, or school intervention teams
• Early-career record of exceptional individual performance—academic, athletic, or professional—prior to assuming leadership roles
• Conviction that the conventional education system is failing and personal commitment to reconstructing it

About Waypoint Academy

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

Pay & Schedule

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