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

The Role

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

What You Will Be Doing

• Develop the Guides on your team: examine performance metrics, observe their student interactions, and conclude each session with concrete actions that address performance gaps.
• Facilitate one-hour outdoor workshops focused on life skills, where students from K-12 develop leadership, grit, collaboration, and communication via adventure-based activities.
• Conduct motivational sessions informed by student analytics and Coachbot insights to drive every student toward goal ownership and personal accountability.
• Maintain your own cohort of students while coaching other Guides, ensuring your leadership emerges from real-time experience rather than past recollection.
• Monitor student engagement, goal achievement, and Guide effectiveness on a weekly basis to identify and address underperformance early.

Basic 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 5 years of 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 termination
• Hands-on experience working with youth aged 5-18 in educational or developmental contexts
• Record of building, launching, or substantially expanding a program, team, school, or outdoor initiative from inception, supported by a measurable, specific example
• Documented ability to leverage data and metrics for goal-setting and decision-making, not solely for reporting

Nice-to-have Requirements

• Master's degree in a relevant discipline
• Experience coaching sports, leading wilderness or experiential education programs, managing camps, or directing youth programs at scale with cohort management and outcome measurement
• Transitioned from classroom teaching into program development or operations roles in EdTech, tutoring organizations, youth-focused nonprofits, or school intervention teams
• History of exceptional individual performance—academic, athletic, or professional—early in your career, prior to entering leadership
• Conviction that traditional education structures are fundamentally flawed and a personal commitment to reimagining them

About Waypoint Academy

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