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

About the role

On-site at Waypoint Academy in Dripping Springs, Texas. $150,000/year as a W2 employee, paid weekly. Day-one health benefits. Relocation support available. The most supportive thing you can do for a kid is hand them something hard and refuse to carry it for them. If that makes you uneasy, stop reading. If it makes you nod, keep going. At Waypoint Academy, core academics run on self-guided, AI-powered adaptive apps that compress the school day into a focused morning. No lectures. That frees you for the work that actually changes a kid's trajectory. Your morning might open with a one-on-one coaching session with a Guide, reviewing student data to find where a cohort is slipping. By midday you're outdoors, leading a workshop that teaches teamwork and resilience through a real challenge. Afternoons shift to motivation sessions: sitting with individual students, learning what drives them, and getting a resistant kid moving toward their goals. You carry your own cohort the whole time, so you stay sharp on the skills you coach in others. You've probably been the square peg in youth programming: too data-driven, too results-focused, too willing to take kids outside and