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

About the role

At Waypoint Academy, core academics run on self‑guided, AI‑powered adaptive apps that compress the school day into a focused morning with no lectures. The role frees you to do the work that actually changes a kid’s trajectory: one‑on‑one coaching sessions with Guides, outdoor workshops that teach teamwork and resilience, and motivation sessions that help students own their progress. You will coach Guides, lead outdoor life‑skill workshops, and carry your own cohort while developing others.

Responsibilities

• 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.
• Building curriculum or lesson plans from scratch.
• Coaching Guides on teaching technique (the focus is on motivation, accountability, and presence with kids).
• Lowering the bar to keep the peace.
• Keeping kids inside and in their seats; most learning happens outdoors through challenge.

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.

Preferred Qualifications

• 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.

Benefits

Immediate access to the standard W‑2 employee benefits package offered by Crossover (details at the company benefits page).

Compensation

This full‑time, year‑long position is a W‑2 employee role with a compensation level of $150,000 USD per year, paid weekly.