Youth Program Director, Waypoint Academy - $150,000/year USD

On-site position at Waypoint Academy, Dripping Springs, Texas.

About the role

The best thing you can do for a child is to give them a difficult challenge and refuse to solve it for them. If that idea troubles you, this role isn't for you. If it resonates, read on.

Waypoint Academy delivers core academic instruction through self-directed, AI-powered adaptive platforms that condense traditional school hours into a concentrated morning block. No conventional teaching. This structure frees you to focus on the work that genuinely shifts student outcomes. Your morning may begin with a one-on-one strategy session with a Guide, analyzing student performance data to pinpoint where a group is struggling. By midday, you're outside running a workshop that builds teamwork and grit through hands-on challenges. Afternoons are reserved for individual motivation work: sitting with students, identifying what drives them, and helping an unmotivated kid commit to their own progress. You maintain your own student cohort throughout, ensuring you stay grounded in the skills you're coaching others to develop.

You've likely been the misfit in traditional education: too metric-oriented, too outcome-focused, too comfortable letting kids face real difficulty. This could be the first environment where you belong. You begin coaching Guides immediately, and as you produce results, the benchmark you establish spreads throughout the cohort and your authority over programming expands. You'll witness the impact firsthand: a doubtful kid who begins taking ownership of their learning, a Guide who improves because you gave them honest feedback, a student who emerges from an outdoor challenge more confident than when they entered.

Responsibilities

• Develop the Guides on your team: analyze performance metrics, observe their interactions with students, and conclude each coaching session with concrete actions that address performance gaps.
• Facilitate one-hour outdoor skill-building workshops 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 student cohort while mentoring other Guides, ensuring you coach from live practice rather than past experience.
• Monitor student satisfaction scores, goal achievement rates, and Guide effectiveness on a weekly basis to identify underperformance early.
• Ensure every student in your cohort loves coming to school, achieves academic growth, and develops the character and practical skills necessary to succeed in life.

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring. Students engage with self-paced adaptive platforms, frequently without direct adult supervision.
• Creating original curriculum or detailed lesson plans. The frameworks already exist; your responsibility is execution quality and commitment, not innovation.
• Training Guides on instructional methods. Since Guides don't teach traditionally, you coach them on student motivation, accountability, and presence.
• Compromising standards to avoid conflict. You will not advance an underperforming student or overlook a Guide's failure to meet expectations.
• Confining students to indoor classrooms. A significant portion of learning at Waypoint occurs outside through experiential challenge.

Requirements

• 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 related discipline
• Minimum of 5 years 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-based terminations
• Hands-on experience working with youth between the ages of 5 and 18 in educational or developmental contexts
• Experience building, launching, or meaningfully expanding a program, team, school, or outdoor initiative from inception, with a concrete and measurable example
• Documented ability to leverage data and performance metrics to establish objectives and inform decisions, not simply to report outcomes
• Legal authorization to work in the United States

Nice-to-have Requirements

• Master's degree in a relevant discipline
• Background coaching athletics, directing wilderness or experiential education programs, managing camps, or overseeing youth programs at a scale requiring cohort management and outcome measurement
• Transitioned from classroom teaching to building or leading programs in a different capacity: EdTech, tutoring organizations, youth-focused nonprofits, or school-based intervention teams
• Record of exceptional individual performance early in your career—academically, athletically, or professionally—prior to assuming leadership responsibilities
• Conviction that the conventional education system is fundamentally flawed and personal commitment to rebuilding it

About Waypoint Academy

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

Pay

$150,000 annual salary as a W2 employee with weekly pay.

Benefits

• Health benefits start on day one
• Relocation assistance provided