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

About the Role

The greatest gift you can give a young person is to present them with a real challenge and resist the urge to solve it for them. If that statement unsettles you, this role isn't for you. If it resonates, read on. Waypoint Academy structures its core academic instruction around self-paced, AI-driven adaptive platforms that condense the traditional school day into a concentrated morning block. There are no lectures.

This structure liberates you to focus on the work that genuinely alters a student's path. Your day may begin with a coaching conversation alongside a Guide, analyzing student performance data to pinpoint where a group is struggling. By late morning you're facilitating an outdoor session designed to build teamwork and grit through experiential challenge. Afternoons are reserved for individual motivation work: connecting with students one-on-one, uncovering what drives them, and mobilizing those who are stuck.

Responsibilities

• Provide direct coaching to Guides: analyze their performance metrics, observe their student interactions, and conclude each session with concrete action steps that address performance gaps.
• Facilitate one-hour outdoor workshops focused on life skills, where students from K-12 develop leadership, resilience, collaboration, and communication through adventure-based learning.
• Conduct individual motivation sessions informed by student analytics and Coachbot insights to drive every student toward their objectives and cultivate ownership of their learning.
• Maintain your own student cohort while simultaneously mentoring Guides, ensuring your coaching is grounded in present-day practice rather than outdated recollection.
• Monitor student satisfaction, goal attainment, and Guide effectiveness on a weekly basis to identify and address underperformance early.

What You Won’t Be Doing

• Delivering lectures or academic tutoring. Students engage with content via self-directed adaptive technology, frequently without direct adult supervision.
• Creating new curriculum or designing lesson plans. Established playbooks are in place; your focus is execution fidelity and engagement, not innovation.
• Training Guides on instructional methods. Since Guides do not lecture, you coach on student motivation, accountability, and relational presence.
• Compromising standards for comfort. You will not advance underperforming students or overlook a Guide's failure to meet expectations.
• Confining students indoors or to seated activities. A significant portion of learning at Waypoint occurs outside, through challenge-based experiences.

Requirements

• Available to work on-site at Waypoint Academy, Dripping Springs, Texas
• Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or related discipline
• Minimum of 5 years of professional 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 termination
• Hands-on experience working with youth aged 5-18 in an educational or developmental capacity
• Experience building, launching, or significantly scaling a program, team, school, or outdoor initiative from inception, supported by a concrete and measurable example
• Documented proficiency using data and metrics to establish goals and inform decisions, not merely for reporting purposes
• Authorized to work legally in the United States

Nice-to-have Requirements

• Master's degree in a relevant discipline
• Background coaching athletics, directing wilderness or experiential programs, managing camps, or overseeing youth programs at a scale requiring cohort management and outcome measurement
• Transitioned from classroom teaching into program-building roles in EdTech, tutoring organizations, youth-focused nonprofits, or school intervention initiatives
• Track record of exceptional individual performance—academic, athletic, or professional—early in your career, prior to stepping into leadership
• Conviction that the traditional education system is fundamentally flawed and a personal commitment to reimagining it

Benefits

$150,000 annual salary as W2 employee with weekly pay and health benefits starting day one. Relocation assistance provided.