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

What You Will Be Doing

• Develop the Guides working with you: analyze performance metrics, observe their interactions with students, and conclude each session with concrete action steps that address performance gaps.
• Facilitate one-hour outdoor workshops focused on life skills, where K-12 students develop leadership, resilience, teamwork, and communication through adventure-based activities.
• Conduct motivation sessions leveraging student analytics and Coachbot data to ensure every student advances toward their objectives and takes ownership of their development.
• Maintain your own student cohort while simultaneously mentoring other Guides, ensuring your coaching comes from active practice rather than past experience.
• Monitor student satisfaction, goal attainment, and Guide effectiveness on a weekly basis to identify and address underperformance early.

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring to students.
• Creating curriculum or designing lesson plans from the ground up.
• Training Guides on instructional methods.
• Reducing expectations to avoid conflict.
• Confining students indoors and to desks.

About the Role

Located on-site at Waypoint Academy in Dripping Springs, Texas
$150,000 annual salary as a W2 employee, with weekly pay.
Health benefits begin on day one.
Relocation assistance provided
The most valuable thing you can offer a young person is a difficult challenge paired with the refusal to solve it for them.

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 field
• 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 responsibility for 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 expanding 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 merely to report outcomes

Nice-to-have Requirements

• Master's degree in a relevant discipline
• Background 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 lead programs in a different capacity: EdTech, tutoring, youth nonprofits, or school intervention teams
• Early-career history of exceptional individual performance—academic, athletic, or professional—prior to transitioning into leadership roles
• Conviction that the conventional education model is fundamentally flawed and personal commitment to reconstructing it

Benefits

Immediate availability
Full-time (40 hours per week)
Long-term position
Weekly pay
$75 USD/hour, which equates to $150,000 USD/year assuming 40 hours per week and 50 weeks per year

Schedule

Immediately available

Pay

$75 USD/hour, which equates to $150,000 USD/year assuming 40 hours per week and 50 weeks per year