Youth Development Director, Waypoint Academy

On‑site role at Waypoint Academy, Dripping Springs, Texas. Compensation: $150,000 annually (W2 employee). Weekly pay. Health coverage begins on day one. Relocation assistance available.

Waypoint Academy delivers core academics through self‑paced, AI‑driven adaptive platforms that consolidate formal instruction into a concentrated morning block. The work is structured to focus on coaching, outdoor adventure-based workshops, and individualized student motivation.

• Provide coaching to the Guides on your team: analyze performance metrics, observe their interactions with students, and conclude each session with clear, actionable next steps that address performance gaps.
• Facilitate one‑hour outdoor life‑skills workshops where students from K‑12 develop leadership, grit, collaboration, and communication skills through adventure‑based activities.
• Conduct motivation sessions that leverage student analytics and Coachbot insights to propel every student toward goal achievement and personal accountability.
• Maintain your own student cohort while simultaneously developing other Guides, ensuring your coaching stems from active practice rather than past experience.
• Monitor student satisfaction scores, goal attainment rates, and Guide performance metrics on a weekly basis to identify and address underperformance early.

• Delivering lectures or providing academic tutoring. Students progress through self‑directed adaptive technology, frequently without direct adult instruction.
• Creating curriculum or designing lesson plans. Established frameworks are in place; your focus is on execution quality and engagement, not innovation.
• Training Guides on instructional pedagogy. Since Guides do not lecture, your coaching centers on motivation tactics, accountability systems, and interpersonal presence.
• Compromising standards to avoid conflict. You will not advance a student prematurely or overlook underperformance among Guides.
• Confining students to indoor, seated learning. A significant portion of development at Waypoint occurs outdoors through experiential challenge.

Ensure that every student in your cohort develops a genuine love for school, demonstrates academic growth, and acquires the character and practical skills necessary for long‑term success.

• Willing 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 termination decisions
• Hands‑on experience working with youth ages 5‑18 in educational or developmental contexts
• Experience building, launching, or substantially scaling a program, team, school, or outdoor initiative from inception, with a concrete and measurable outcome
• Documented use of data and performance metrics to establish objectives and inform decision‑making, beyond simple reporting
• Legal authorization to work in the United States

• Master’s degree in a relevant field
• Background coaching athletics, leading wilderness or experiential education programs, managing camps, or directing youth initiatives at a scale requiring cohort management and outcome tracking
• Transitioned out of classroom teaching to develop or lead programs in a different capacity:
  EdTech, tutoring services, youth‑focused nonprofits, or school intervention initiatives
• Strong early‑career performance record—academic, athletic, or professional—prior to stepping into leadership roles
• Conviction that conventional education systems are inadequate and personal commitment to reforming them

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

Health coverage begins on day one; relocation assistance provided.