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

The Role

In-person position at Waypoint Academy, Dripping Springs, Texas
Annual salary: $150,000 as a W2 employee with weekly pay.
Health benefits begin day one.
Relocation assistance provided.

What You Will Be Doing

• Develop the Guides on your team: analyze performance metrics, observe their interactions with students, and conclude each session with targeted actions that address specific gaps.
• Facilitate one-hour outdoor workshops focused on life skills, where K-12 students develop leadership, communication, resilience, and teamwork through experiential, adventure-based activities.
• Conduct individualized motivation sessions informed by student analytics and Coachbot insights to drive each student toward goal ownership and consistent progress.
• Maintain your own student cohort alongside coaching responsibilities, ensuring your guidance is rooted in active, current practice rather than past experience.
• Monitor student satisfaction metrics, goal achievement rates, and Guide performance on a weekly basis to identify and address underperformance early.

Basic Requirements

• Able 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' experience 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 directly with youth aged 5-18 in educational or developmental contexts
• Experience building, launching, or substantially scaling a program, team, school, or outdoor initiative, supported by a concrete, measurable example
• Documented ability to leverage data and performance metrics to inform goal-setting and decision-making, beyond simple reporting

Nice-to-have Requirements

• Master's degree in a relevant discipline
• Background in coaching athletics, leading wilderness or experiential education programs, overseeing camps, or managing youth programs with cohort structures and measurable outcome tracking
• Transitioned out of classroom teaching to design or lead programs in other capacities: EdTech, tutoring services, youth-focused nonprofits, or school intervention initiatives
• Strong early-career performance record—academic, athletic, or professional—prior to assuming leadership responsibilities
• Conviction that conventional education systems are fundamentally flawed and personal commitment to reimagining them

About Waypoint Academy

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

Legal Authorization

Legal authorization to work in the United States

Crossover Job Code

LJ-5818-US-Dripping-YouthDevelopme.003