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

About the Role

Waypoint Academy runs core academics through self-guided, AI-powered adaptive software that condenses the school day into a concentrated morning session. No traditional instruction. That structure creates space for the work that genuinely shifts a student's path.

You might begin your morning in a one-on-one coaching conversation with a Guide, analyzing student data to identify where a cohort needs support. By midday, you're outside facilitating a workshop that builds teamwork and resilience through authentic challenge. Afternoons are devoted to motivation work: meeting with individual students, identifying what motivates them, and helping a reluctant learner engage with their own goals. You maintain responsibility for your own cohort throughout, keeping your coaching grounded in active practice rather than theory.

You may have felt out of place in traditional education: too focused on data, too results-oriented, too ready to bring students outside and allow them to face difficulty. This may be the environment where you belong. You begin coaching other Guides immediately, and as you produce results, the expectations you establish influence the entire cohort and your impact on the program expands. You witness the outcomes directly: a doubtful student who begins taking ownership of their development, a Guide who improves because you offered honest feedback, a young person who emerges from the wilderness more competent than when they entered.

What You Will Be Doing

• Provide coaching to the Guides working with you: analyze performance metrics, observe their interactions with students, and conclude each session with concrete actions that 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 progresses toward their goals and takes ownership of their development.
• Maintain your own student cohort while coaching other Guides, ensuring your guidance comes from ongoing experience rather than past recollection.
• Monitor student satisfaction, goal completion rates, and Guide performance on a weekly basis to identify underperformance before it escalates.

What You Won't Be Doing

• Delivering lectures or academic tutoring to students. Academic content is delivered through self-guided adaptive applications, frequently without direct adult supervision.
• Developing curriculum or lesson plans from the ground up. The frameworks are already in place; success depends on faithful execution and energy, not creative invention.
• Training Guides on instructional methods. Since Guides do not lecture, you focus on coaching motivation, accountability, and their presence with students.
• Compromising standards to maintain harmony. You will not advance a student without merit or overlook a Guide's insufficient performance.
• Confining students indoors and seated. A significant portion of learning occurs outside through challenge-based experiences.

Outdoor Education Director Key Responsibilities

• Ensure that every student in your cohort loves school, demonstrates academic growth, and develops the character and life 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 a related field
• Minimum of 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 decisions
• Direct experience working with youth ages 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 specific and measurable example
• Documented use of data and metrics to establish goals and inform decisions, not merely to report outcomes
• Legal authorization to work in the United States

Nice-to-have Requirements

• Master's degree in a related field
• Experience coaching athletics, leading wilderness or experiential programs, directing camps, or managing youth programs at a scale requiring cohort management and outcome measurement
• Transitioned from classroom teaching to program development or leadership roles in EdTech, tutoring, youth nonprofits, or school intervention teams
• Early-career history of exceptional individual performance—academic, athletic, or professional—prior to assuming leadership responsibilities
• Conviction that the conventional education model is ineffective and personal commitment to its transformation

About Waypoint Academy

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

Pay and Schedule

This is a full-time, W2 employee position with weekly pay. Compensation is $150,000 USD/year. Health benefits begin day one. Relocation assistance provided. All roles are year-long positions.