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

About Waypoint Academy

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

What You Will Be Doing

• Coach the Guides who work alongside you: review performance data, observe them with students, and end every session with specific actions that close the gap.
• Lead one-hour outdoor life-skill workshops where K-12 students build leadership, resilience, teamwork, and communication through adventure-based challenges.
• Run motivation sessions using student analytics and Coachbot data to get every student moving toward their goals and owning their own progress.
• Carry your own student cohort while developing other Guides, so you coach from current experience, not memory.
• Track student satisfaction, goal completion, and Guide performance weekly to catch underperformance before it compounds.

What You Won't Be Doing

• Lecturing or tutoring students on academic subjects. They learn through self-guided adaptive apps, often with no adult in the room.
• Building curriculum or lesson plans from scratch. The playbooks exist; the bar is fidelity and energy, not originality.
• Coaching Guides on teaching technique. Guides don't lecture, so you coach motivation, accountability, and how they show up with kids.
• Lowering the bar to keep the peace. You won't pass a student along or smooth over a Guide's underperformance.
• Keeping kids inside and in their seats. Much of the learning here happens outdoors, through challenge.

Key Responsibilities

• Make sure every student in your cohort loves school, grows academically, and builds the character and life skills to thrive.

Basic Requirements

• Willing to work in person at Waypoint Academy in Dripping Springs, Texas
• Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or a related field
• At least 5 years in education, youth development, coaching, outdoor education, or learning and development (L&D)
• Track record of leading a team of 5 or more adults, including hiring and performance-based termination decisions
• Direct experience working with youth ages 5-18 in an educational or developmental setting
• Built, launched, or significantly grew a program, team, school, or outdoor initiative from the ground up, with a specific and measurable example
• Proven use of data and metrics to set goals and drive decisions, not just report results
• Legally authorized to work in the United States

Nice-to-have Requirements

• Master's degree in a related field
• Coached athletics, led wilderness or experiential programs, directed camps, or ran youth programs at a scale that required running cohorts and measuring outcomes
• Left classroom teaching to build or run programs from a different seat: EdTech, tutoring, youth nonprofits, or school intervention teams
• Early-career track record of high personal performance, academic, athletic, or professional, before moving into leadership
• Belief that the standard education model is broken and personal investment in rebuilding it

Pay

$150,000/year as a W2 employee, paid weekly.

Benefits

Day-one health benefits.

Schedule

Full-time position.