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

• Based on-site at Waypoint Academy in Dripping Springs, Texas
• Annual salary of $150,000 as a W2 employee, with weekly pay. Health benefits begin on day one.
• Relocation assistance provided

The greatest gift you can give a young person is something difficult—and the refusal to take it off their hands. If that philosophy unsettles you, this isn't the role for you. If it resonates, read on.

Waypoint Academy structures core academics around self-directed, AI-powered adaptive platforms that condense the traditional school day into a concentrated morning session. No traditional lectures. That design frees you to focus on the work that genuinely shifts a student's path. Your morning may begin with a coaching conversation alongside a Guide, examining student performance data to identify where a group is falling behind.

By midday, you're outside running a workshop that builds teamwork and grit through authentic challenge. Afternoons are reserved for motivational work: sitting down with individual students, understanding what moves them, and pushing a disengaged kid toward action on their own goals. You maintain your own student cohort throughout, keeping your coaching grounded in live practice rather than theory.

You've likely been the outlier in traditional education: too metrics-focused, too outcome-oriented, too comfortable taking students into the field and letting them wrestle with real difficulty. This may be the first environment that values exactly that. You begin coaching other Guides immediately, and as you produce measurable results, the benchmark you establish influences the entire cohort and your authority within the program expands.

You witness the impact directly: a doubtful student who begins taking ownership, a Guide who sharpens after you gave them honest feedback, a young person who returns from the wilderness more competent than when they left.

• Mentor the Guides on your team: analyze performance metrics, observe their interactions with students, and conclude each session with concrete actions that address performance gaps.
• Facilitate one-hour outdoor life-skills workshops where students from K-12 develop leadership, grit, collaboration, and communication through experiential, adventure-based activities.
• Conduct motivational sessions informed by student analytics and Coachbot insights to drive every student toward goal ownership and forward progress.
• Maintain your own student cohort alongside your coaching duties, ensuring your guidance to other Guides comes from active, real-time experience rather than past recollection.
• Monitor student satisfaction, goal achievement, and Guide effectiveness on a weekly basis to identify and address underperformance early.

• Delivering lectures or providing academic tutoring to students. They engage with content via self-paced adaptive applications, frequently without direct adult supervision.
• Designing curriculum or creating lesson plans from the ground up. Established frameworks are already in place; your focus is on consistent execution and engagement, not innovation.
• Training Guides on instructional pedagogy. Since Guides do not lecture, your coaching centers on motivation, accountability, and interpersonal presence with students.
• Compromising standards to avoid conflict. You will not advance a student who hasn't earned it or overlook a Guide's inadequate performance.
• Confining students indoors or to desks. A significant portion of learning at Waypoint occurs outside, through structured challenge.

Ensure every student in your cohort develops a genuine love of school, advances academically, and cultivates the character and life skills necessary for long-term success.

• Available 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' experience in education, youth development, coaching, outdoor education, or learning and development (L&D)
• Demonstrated history of managing a team of 5 or more adults,…