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

• Based on-site at Waypoint Academy in Dripping Springs, Texas
• $150,000 annually as a W2 employee, with weekly pay. Health benefits begin day one.
• Relocation assistance provided
  
  

The most powerful support you can offer a young person is to give them a challenge and let them carry it themselves. If that idea unsettles you, this role isn't for you. If it resonates, read on.

Waypoint Academy structures core academics around self-directed, AI-driven adaptive platforms that condense the traditional school day into a concentrated morning block. No classroom instruction. That design creates space for the work that genuinely shifts outcomes for students. Your mornings may begin with one-on-one coaching alongside a Guide, analyzing student performance data to identify where a group is struggling. By midday you're outside, facilitating a workshop that builds teamwork and resilience through hands-on challenges. Afternoons are reserved for motivation work: meeting individually with students, understanding what drives them, and moving a reluctant learner toward meaningful goals. You maintain your own student cohort throughout, ensuring you coach from live experience rather than theory.

You've likely been the outlier in traditional education: too metric-focused, too outcome-oriented, too comfortable taking students outside and letting them face difficulty. This may be the first environment that aligns. You begin coaching other Guides immediately, and as you produce results, the expectations you establish influence the entire cohort and your impact on the program deepens. You'll witness the outcomes directly: a doubtful student who begins taking ownership of their development, a Guide who sharpens because you offered honest feedback, a young person who emerges from a challenge more capable than before.

Maintain the standard. Get them outdoors. Apply today.

What You Will Be Doing

• Mentor the Guides working with you: analyze performance metrics, observe their interactions with students, and conclude each session with clear next 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 experiential challenges.
• Conduct motivation sessions informed by student analytics and Coachbot data to ensure every student progresses toward their objectives and takes ownership of their development.
• Maintain your own student cohort while guiding other Guides, ensuring your coaching is grounded in active practice, not past experience.
• Monitor student satisfaction, goal achievement, and Guide performance on a weekly basis to identify underperformance early.
  
  

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring. Students engage with self-directed adaptive platforms, frequently with no adult present.
• Creating curriculum or lesson plans from the ground up. Established frameworks are in place; success depends on execution and energy, not innovation.
• Training Guides in instructional methods. Guides don't lecture, so your coaching focuses on motivation, accountability, and presence with students.
• Compromising standards to avoid conflict. You will not advance a student prematurely or overlook underperformance in a Guide.
• Confining students to indoor, seated learning. Much of the meaningful work here occurs outside, through challenge-based experiences.
  
  

Youth Development Director Key Responsibilities

Ensure every student in your cohort is engaged in school, demonstrates academic growth, and develops the character and life skills necessary to succeed.

Basic Requirements

• Available to work on-site at Waypoint Academy in Dripping Springs, Texas
• Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or related discipline
• Minimum of 5 years in education, youth development, coaching, outdoor education, or learning and development (L&D)
• Demonstrated history of managing a team of 5 or more adults, including responsibility for hiring and performance-related termination decisions
• Hands-on experience working with youth ages 5-18 in educational or developmental contexts
• 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 objectives and inform decisions, not solely for reporting purposes
• Legal authorization to work in the United States
  
  

Nice-to-have Requirements

• Master's degree in a relevant discipline
• Background coaching athletics, leading wilderness or experiential education programs, directing camps, or managing youth programs at a scale requiring cohort management and outcome measurement
• Transitioned from classroom teaching to program development or operations in EdTech, tutoring organizations, youth-focused nonprofits, or school intervention initiatives
• History of exceptional personal performance early in career—academic, athletic, or professional—prior to entering leadership
• Conviction that conventional education models are ineffective and personal commitment to transforming them
  
  

About Waypoint Academy

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

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

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-YouthDevelopme.008