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

The Role

Waypoint Academy offers a unique on-site role in Dripping Springs, Texas, with an annual salary of $150,000 as a W2 employee, including weekly pay. Health benefits commence on day one, and relocation assistance is provided.

What You Will Be Doing

• Mentor the Guides working with you: analyze performance metrics, observe interactions with students, and conclude each session with targeted actions addressing identified gaps.
• Facilitate one-hour outdoor life-skills workshops where students in grades K-12 develop leadership, grit, collaboration, and communication through adventure-based activities.
• Conduct motivational coaching sessions informed by student analytics and Coachbot insights to activate every learner toward their objectives and cultivate ownership of their progress.
• Maintain your own student cohort while guiding other educators, ensuring your coaching is rooted in present experience rather than past recollection.
• Monitor student satisfaction, goal achievement, and Guide effectiveness on a weekly basis to identify and address underperformance early.

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 discipline.
• 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 making hiring and performance-based termination decisions.
• Hands-on experience working with youth ages 5-18 in an educational or developmental capacity.
• Experience building, launching, or substantially growing a program, team, school, or outdoor initiative from inception, with a concrete and measurable example.
• Documented use of data and metrics to establish goals and inform decisions, not simply to report outcomes.

Nice-to-have Requirements

• Master's degree in a relevant 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 build or manage programs in a different capacity: EdTech, tutoring, youth nonprofits, or school intervention teams.
• Early-career history of exceptional personal performance—academic, athletic, or professional—prior to entering leadership.
• Conviction that the conventional education model is fundamentally flawed and personal commitment to its transformation.

About Waypoint Academy

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