Camp Director, Waypoint Academy - $150,000/year USD
About the role
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 education: too data-driven, too results-focused, too willing to take kids outside and let them struggle. This might be the first place that fits. You coach other Guides from day one, and as you deliver results, the standard you set ripples across the whole cohort and your influence over the program grows. You'll see the payoff in person: a skeptical kid who starts owning their progress, a Guide who gets sharper because you told them the truth, a student who walks out of the woods more capable than they walked in. Hold the standard. Take them outside.
Responsibilities
- 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.
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
Qualifications
- Master's degree in a related field (nice-to-have)
- 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
Benefits
- Day-one health benefits
- Relocation support available
- Immediate access to benefits (W2 employee)
Pay
$150,000 per year, paid weekly as a W2 employee.
Schedule
Full-time, on‑site position at Waypoint Academy in Dripping Springs, Texas.