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

• Based on-site at Waypoint Academy, Dripping Springs, Texas
• W2 compensation of $150,000 annually, distributed weekly. Full health coverage begins day one.
• Support for relocation provided

The best way to help a child grow is to give them something difficult and let them carry it themselves. If that idea unsettles you, this isn't your role. If you find yourself agreeing, read on.

Waypoint Academy operates with a compressed academic schedule. Core subjects are delivered through self-paced, AI-driven adaptive platforms that students complete each morning without traditional lectures. This structure allows you to focus on the work that truly shapes student outcomes. Your morning may begin with a one-on-one strategy session alongside a Guide, analyzing performance data to identify where a group of students is falling behind.

By midday, you transition outdoors to facilitate workshops that build teamwork and resilience by engaging students in meaningful challenges. Afternoons are dedicated to individual motivation work: connecting with students, understanding what drives them, and helping those who resist take steps toward their own goals. You maintain responsibility for your own cohort throughout, ensuring the skills you teach remain grounded in current practice.

You're likely someone who never quite fit the typical education mold - too focused on outcomes, too reliant on data, too comfortable taking students outside their comfort zones. This may be the environment where that finally makes sense. You begin coaching other Guides immediately, and as your results speak for themselves, the standards you establish influence the broader cohort and expand your impact on the program.

The rewards are tangible: watching a doubtful student begin to take ownership, seeing a Guide improve because you gave honest feedback, observing a student return from an outdoor challenge visibly more confident.

Maintain the standard. Lead them outside.

• Provide coaching to 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 students from K-12 develop leadership, communication, teamwork, and resilience through adventure-based activities.
• Conduct motivation sessions informed by student analytics and Coachbot insights to ensure every student advances toward their goals and takes responsibility for their progress.
• Maintain direct responsibility for your own student cohort while simultaneously mentoring other Guides, ensuring your coaching is rooted in active experience rather than past practice.
• Monitor student satisfaction, goal attainment, and Guide effectiveness on a weekly basis to identify and address underperformance early.

• Delivering lectures or providing academic tutoring. Students advance through self-directed adaptive technology, frequently without direct adult supervision.
• Creating original curricula or detailed lesson plans. The frameworks are already in place; your focus is on faithful execution and high energy, not invention.
• Training Guides in instructional methods. Since Guides do not lecture, your coaching centers on motivation, accountability, and their presence with students.
• Compromising standards to avoid conflict. You will not advance students who haven't earned it or ignore underperformance among Guides.
• Confining students to indoor, seated environments. A significant portion of learning at Waypoint occurs outdoors through physical and mental challenges.

Ensure every student within your cohort develops a genuine love for school, demonstrates academic growth, and acquires the character and life skills necessary for long-term success.

• Available to work on-site at Waypoint Academy, located in Dripping Springs, Texas
• Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or a closely related discipline
• A minimum of 5 years of professional experience in education, youth development, coaching, outdoor education, or learning and development (L&D)
• Demonstrated history of leading a team of at least 5 adults, including responsibility for hiring and performance-related termination decisions
• Hands-on experience working directly with youth between the ages of 5 and 18 in educational or developmental contexts
• Experience building, launching, or substantially scaling a program, team, school, or outdoor initiative from inception, supported by a concrete and measurable example
• Established ability to leverage data and metrics to inform goal-setting and decision-making, not merely for reporting purposes
• Legal authorization to work in the United States

• Master's degree in a relevant discipline
• Experience coaching athletics, leading wilderness or experiential learning programs, directing camps, or…