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

Crossover; Dripping Springs (TX); On-site; USD 135,000 - 165,000; Full time

Benefits offered by this job

Relocation support

Day-one health benefits

Job summary

Waypoint Academy in Dripping Springs, TX, is seeking a Youth Program Director to lead Guides, design outdoor life-skills workshops, and drive student progress using analytics. This full-time, on-site role offers relocation support and a competitive compensation package with day-one health benefits.

You will coach and mentor Guides, oversee cohorts, and ensure each student grows academically, socially, and personally through rigorous, outdoor programming.

Qualifications

• 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.
• Proven use of data and metrics to set goals and drive decisions.
• Direct experience leading a team of 5+ adults.

Responsibilities

• Review performance data, observe Guides with students, and end sessions with specific actions to close gaps.
• 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 move every student toward their goals.
• Carry your own student cohort while developing other Guides, coaching from current experience.
• Track student satisfaction, goal completion, and Guide performance weekly to catch underperformance before it compounds.

Job description

• 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 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.

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.

Youth Program Director 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

About Waypoint Academy

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

Working with us

This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year-long positions. The compensation level for this role is $150,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5818-US-Dripping-YouthProgramDi.016