What are the responsibilities and job description for the Outdoor Education Director, Waypoint Academy - $150,000/year USD position at Crossover?
- Located on-site at Waypoint Academy in Dripping Springs, Texas
- $150,000 annual salary as a W2 employee, with weekly pay. Health benefits begin on day one.
- Relocation assistance provided
Waypoint Academy structures core academics around self-guided, AI-powered adaptive applications that condense the traditional school day into a concentrated morning session. No traditional lectures. This design frees your time for the work that genuinely shifts a student's path. Your morning may begin with a one-on-one strategy session alongside a Guide, analyzing student performance data to identify where a cohort needs intervention. By midday, you're outside facilitating a hands-on workshop that builds teamwork and resilience through authentic challenges. Afternoons transition to individualized motivation work: meeting with students one-on-one, understanding their drivers, and mobilizing a disengaged kid toward meaningful goals. You maintain your own student cohort throughout, ensuring you remain current in the skills you're coaching others to develop.
You've likely been the outlier in educational settings: too metric-focused, too outcome-oriented, too comfortable taking students outdoors and allowing them to struggle productively. This may be the first environment that aligns with your approach. You begin coaching other Guides immediately, and as you produce measurable results, the benchmark you establish influences the entire cohort and your authority within the program expands. You'll witness the impact firsthand: a doubtful student who begins taking ownership of their development, a Guide who sharpens their practice because you offered candid feedback, a young person who emerges from an outdoor experience more self-reliant than when they entered.
Maintain the standard. Get them outside. Apply today.
What You Will Be Doing
- Develop the Guides working with you: analyze performance metrics, observe their interactions with students, and conclude each session with concrete action steps that address performance gaps.
- Facilitate one-hour outdoor workshops focused on life skills, where K-12 students develop leadership, resilience, teamwork, and communication through adventure-based activities.
- Conduct motivation sessions leveraging student analytics and Coachbot data to ensure every student advances toward their objectives and takes ownership of their development.
- Maintain your own student cohort while simultaneously mentoring other Guides, ensuring your coaching comes from active practice rather than past experience.
- Monitor student satisfaction, goal attainment, and Guide effectiveness on a weekly basis to identify and address underperformance early.
- Delivering lectures or providing academic tutoring to students. They engage with content through self-directed adaptive applications, frequently without direct adult supervision.
- Creating curriculum or designing lesson plans from the ground up. The frameworks are established; your focus is on faithful execution and energetic delivery, not creative invention.
- Training Guides on instructional methods. Guides don't lecture, so your coaching centers on motivation, accountability, and their presence with students.
- Reducing expectations to avoid conflict. You won't advance a student who hasn't met the standard or overlook a Guide's performance issues.
- Confining students indoors and to desks. A significant portion of learning at Waypoint occurs outside, through direct challenge.
Ensure every student in your cohort develops a love for school, achieves academic growth, and cultivates the character and life skills necessary for long-term success.
Basic 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 field
- 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 decisions
- Hands-on experience working with youth ages 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 example
- Documented use of data and metrics to establish goals and inform decisions, not merely to report outcomes
- Legal authorization to work in the United States
- Master's degree in a relevant discipline
- Background 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 build or lead programs in a different capacity: EdTech, tutoring, youth nonprofits, or school intervention teams
- Early-career history of exceptional individual performance—academic, athletic, or professional—prior to transitioning into leadership roles
- Conviction that the conventional education model is fundamentally flawed and personal commitment to reconstructing it
Nature-based school that blends rigorous academics with real-world challenges.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $75 USD/hour, which equates to $150,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5818-US-Dripping-OutdoorEducati
Salary : $150,000