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

On-site position at Waypoint Academy in Dripping Springs, Texas.

About the role

The greatest support you can offer a young person is to give them a challenge and let them carry it themselves. If that perspective troubles you, this isn't the right fit. If it resonates, this role may be where you belong.

Waypoint Academy operates on a model where traditional academics happen through self-directed, AI-driven adaptive platforms that condense formal instruction into focused morning sessions. No classroom lectures. This structure opens space for the work that truly shifts a student's path.

Your morning may begin with a one-on-one with a Guide, analyzing student performance data to identify where a group is struggling. By midday, you're outside facilitating a hands-on workshop that builds teamwork and grit through authentic challenge. Afternoons pivot to motivational coaching: meeting with individual students, understanding what drives them, and guiding a reluctant learner toward action. You maintain your own cohort throughout, ensuring your coaching stays grounded in real-time practice.

You'll mentor other Guides from the start, and as your results speak for themselves, the benchmark you establish influences the broader program and expands your impact. The rewards are immediate: a doubtful student who begins to take ownership, a Guide who improves because you gave honest feedback, a young person who emerges from an outdoor challenge more confident than before.

Responsibilities

• Mentor the Guides on your team: analyze performance metrics, observe their interactions with students, and conclude each session with actionable steps to improve.
• Facilitate one-hour outdoor workshops focused on life skills, where students from K-12 develop leadership, grit, collaboration, and communication through experiential challenges.
• Conduct motivational coaching sessions using analytics and Coachbot insights to drive every student toward goal ownership and personal accountability.
• Maintain your own student cohort while guiding other Guides, ensuring your coaching stems from active, current experience rather than past memory.
• Monitor weekly metrics on student engagement, goal achievement, and Guide effectiveness to identify and address underperformance early.
• Ensure that every student in your cohort is engaged with their education, demonstrates academic progress, and develops the character and life skills necessary for long-term success.

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring. Students engage with content through adaptive, self-guided platforms, often independently.
• Creating original curriculum or lesson materials. Proven frameworks are already in place; your role is execution with fidelity and energy.
• Training Guides on instructional methods. Since Guides don't teach traditionally, your focus is on motivation, accountability, and relational presence.
• Compromising standards to avoid conflict. You will not advance a struggling student prematurely or overlook a Guide's performance issues.
• Confining students indoors. A significant portion of learning takes place outside, through deliberate challenge.

Requirements

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 a related discipline.
• Minimum of 5 years of experience in education, youth development, coaching, outdoor education, or learning and development (L&D).
• Demonstrated history of managing a team of at least 5 adults, including responsibility for hiring and performance-based terminations.
• Hands-on experience working with young people ages 5-18 in educational or developmental contexts.
• Experience building, launching, or scaling a program, team, school, or outdoor initiative from inception, with quantifiable outcomes.
• Documented ability to use data and metrics to inform strategy and drive action, beyond passive reporting.
• Legal authorization to work in the United States.

Nice-to-have Requirements

• Master's degree in a relevant field.
• Background coaching athletics, directing wilderness or experiential programs, managing camps, or overseeing youth programs with measurable cohort-level outcomes.
• Transitioned out of classroom teaching to lead or build programs in EdTech, tutoring, youth-focused nonprofits, or school support teams.
• Strong record of individual achievement—academic, athletic, or professional—early in your career, prior to leadership roles.
• Conviction that traditional education systems are failing and a personal commitment to reimagining them.

About Waypoint Academy

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

Pay

$150,000 annually, with weekly pay.

Benefits

• Health benefits begin on day one.
• Relocation assistance provided.