Outdoor Education Director $150,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Description
- Based on-site at Waypoint Academy, Dripping Springs, Texas
- Annual compensation of $150,000 as a W2 employee with weekly pay. Health benefits begin day one.
- Support available for relocation
The best thing you can offer a young person is a difficult task and the refusal to carry it for them. If that statement unsettles you, you can stop here. If it resonates, continue.
Waypoint Academy runs core academics through self-guided, AI-powered adaptive applications that condense the traditional school day into a concentrated morning block. There are no lectures. That structure frees your time for the work that genuinely shifts a student's path. Your mornings may begin with a coaching session alongside a Guide, analyzing student performance data to identify where a group is falling behind. By midday, you're outside facilitating a workshop that builds teamwork and resilience through authentic challenge. Afternoons transition to motivational work: meeting individually with students, discovering what motivates them, and moving disengaged kids toward meaningful goals. You maintain your own student cohort throughout, ensuring you remain current in the skills you develop in others.
You've likely been the outlier in educational settings: too reliant on data, too focused on outcomes, too comfortable taking students outside and allowing them to struggle. This may be the first environment where that approach is the standard. You begin coaching other Guides immediately, and as you produce measurable results, the expectations you establish spread across the cohort and your influence over the program expands. The impact is visible: a doubtful student begins to take ownership of their progress, a Guide improves because you gave them honest feedback, a young person leaves the wilderness more capable than when they entered.
Uphold the standard. Get them outdoors. Submit your application.
What you will be doing
- Provide coaching to the Guides working with you: analyze performance metrics, observe their interactions with students, and conclude each session with concrete actions that address performance gaps.
- Facilitate one-hour outdoor life-skill sessions where students in grades K-12 develop leadership, resilience, teamwork, and communication skills through adventure-based activities.
- Conduct motivation sessions leveraging 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 mentoring other Guides, ensuring your coaching stems from active practice rather than past recollection.
- Monitor student satisfaction, goal achievement, and Guide effectiveness on a weekly basis to identify underperformance early.
What you will NOT be doing
- Delivering lectures or providing academic tutoring. Students engage with self-guided adaptive applications, frequently without adult supervision in the room.
- Creating curriculum or lesson plans from the ground up. The frameworks are already in place; your focus is on faithful execution and energy, not innovation.
- Training Guides on instructional methods. Since Guides don't lecture, your coaching centers on motivation, accountability, and their presence with students.
- Compromising standards to avoid conflict. You will not advance a student prematurely or overlook a Guide's poor performance.
- Confining students indoors or to seated work. A significant portion of learning here occurs outside, through challenge-based experiences.
Key responsibilities
Ensure that every student in your cohort develops a love for school, achieves academic growth, and builds the character and life skills necessary to succeed.
Candidate 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 of experience 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-based termination decisions
- Hands-on experience working with youth aged 5-18 in educational or developmental contexts
- Experience building, launching, or substantially expanding a program, team, school, or outdoor initiative from inception, with a measurable and specific example
- Documented use of data and metrics to establish goals and inform decisions, beyond simple reporting
- Legal authorization to work in the United States
Nice to have
- Master's degree in a related discipline
- Experience coaching athletics, leading wilderness or experiential programs, managing camps, or overseeing youth programs at scale with cohort management and outcome measurement
- Transitioned from classroom teaching to program development or operations in different capacities: EdTech, tutoring services, youth-focused nonprofits, or school intervention programs
- Early-career history of strong individual performance—academic, athletic, or professional—prior to entering leadership roles
- Conviction that the conventional education model is ineffective and personal commitment to reimagining it
Applying for a role? Here’s what to expect.
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