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 salary of $150,000 as a W2 employee with weekly pay. Health benefits begin on day one.
- Relocation assistance provided
The greatest gift you can give a young person is a meaningful challenge and the refusal to do it for them. If that statement unsettles you, this role isn't for you. If it resonates, read on.
Waypoint Academy structures core academics around self-directed, AI-driven adaptive platforms that condense classroom instruction into a concentrated morning block. There are no traditional lectures. That structural choice frees your time for the work that genuinely shifts a student's path. Your morning may begin with a one-on-one strategy session with a Guide, analyzing student performance data to identify where a group is losing ground. By midday, you're outside facilitating a hands-on workshop that builds teamwork and grit through authentic challenge. Afternoons are dedicated to motivation coaching: direct conversations with individual students to understand their drivers and re-engage those who have checked out. You maintain your own cohort throughout, ensuring the skills you develop in others remain grounded in daily practice.
You've likely been the outlier in education: too metric-focused, too outcome-oriented, too comfortable putting kids in difficult situations and letting them work through it. This may be the first environment where that approach is valued. You begin coaching Guides immediately, and as your results accumulate, the benchmark you establish influences the entire cohort and your authority within the program expands. The impact is tangible: a doubtful student who begins to take ownership, a Guide who improves because you gave them honest feedback, a young person who emerges from an outdoor experience more self-reliant than before.
Maintain the standard. Get them outdoors. Apply today.
What you will be doing
- Provide coaching to the Guides on your team: analyze performance metrics, observe their student interactions, and conclude each session with actionable steps that address identified gaps.
- Facilitate one-hour outdoor workshops focused on life skills, where K-12 students develop leadership, grit, collaboration, and communication through challenge-based activities.
- Conduct motivation coaching sessions informed by student analytics and Coachbot data to drive every student toward goal achievement and personal accountability.
- Maintain your own student cohort alongside your Guide development responsibilities, ensuring your coaching is informed by active, current practice rather than past experience.
- Monitor student satisfaction, goal attainment, and Guide effectiveness on a weekly basis to identify and address underperformance early.
What you will NOT be doing
- Delivering lectures or providing academic tutoring. Students engage with content through self-directed adaptive technology, frequently without direct adult supervision.
- Designing curriculum or creating lesson plans. Existing frameworks are in place; your focus is on faithful execution and sustained energy, not creative development.
- Training Guides in instructional methods. Since Guides do not lecture, your coaching centers on motivation, accountability, and interpersonal presence with students.
- Compromising standards to avoid conflict. You will not advance underperforming students or overlook a Guide's lack of results.
- Confining students to indoor, seated learning. A significant portion of the educational experience occurs outdoors through experiential challenge.
Key responsibilities
Ensure that every student within your cohort develops a genuine love for school, demonstrates academic growth, and cultivates the character and life skills necessary for long-term success.
Candidate requirements
- 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 leading a team of 5 or more 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 substantially expanding a program, team, school, or outdoor initiative from inception, with a concrete and measurable outcome
- Documented application of data and metrics to establish objectives and inform decisions, beyond simply reporting outcomes
- Legal authorization to work in the United States
Nice to have
- Master's degree in a relevant field
- Background in coaching athletics, leading wilderness or experiential programs, directing camps, or managing youth programs at a scale requiring cohort management and outcome measurement
- Transitioned from classroom teaching to program leadership in a different capacity: EdTech, tutoring organizations, youth nonprofits, or school-based intervention teams
- Record of exceptional personal performance early in your career—academic, athletic, or professional—prior to entering leadership roles
- Conviction that the conventional education model is failing and personal commitment to reimagining it
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