What are the responsibilities and job description for the Outdoor Education Director, Waypoint Academy - $150,000/year USD position at Crossover?
- Based on-site at Waypoint Academy, Dripping Springs, Texas
- Annual compensation of $150,000 as a W2 employee with weekly pay. Full health benefits begin day one.
- Relocation assistance provided
Waypoint Academy delivers core academics through self-directed, AI-powered adaptive platforms that condense formal instruction into a concentrated morning block. No traditional lectures. That structure frees you to focus on the interventions that truly shift a student's path. A typical morning may begin with a one-on-one coaching conversation with a Guide, analyzing student performance data to identify where a cohort is struggling. By midday, you're outside facilitating a hands-on workshop that builds teamwork and resilience through authentic challenge. Afternoons are dedicated to motivational work: meeting individually with students, understanding their drivers, and moving disengaged learners toward their own goals. You maintain your own student cohort throughout, keeping your coaching grounded in live practice rather than theory.
You've likely felt out of place in traditional education: too metric-focused, too outcome-oriented, too comfortable taking students into the field and letting them face real difficulty. This may be the first environment that aligns with how you work. You begin coaching other Guides immediately, and as your results accumulate, the benchmark you establish influences the entire cohort and your scope of impact expands. The outcomes are visible and immediate: a skeptical student who begins to take ownership, a Guide who sharpens their approach because you gave direct feedback, a learner who returns from the field more competent than when they left.
Uphold the standard. Lead them outdoors. Apply today.
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 next 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 challenge-based activities.
- Conduct motivation sessions informed by student analytics and Coachbot data, ensuring every student progresses toward their goals and takes responsibility for their development.
- Maintain your own student cohort while mentoring other Guides, grounding your coaching in active, current practice rather than past experience.
- Monitor student satisfaction, goal attainment, and Guide performance on a weekly basis to identify and address underperformance early.
- Delivering lectures or academic tutoring. Students engage with content via self-guided adaptive apps, frequently without direct adult supervision.
- Creating curriculum or designing lesson plans from the ground up. Established playbooks are in place; execution fidelity and energy are the priorities, not innovation.
- Training Guides on instructional methods. Since Guides do not lecture, your coaching centers on motivation, accountability, and relational presence.
- 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 at Waypoint occurs outside through experiential challenge.
Ensure that every student in your cohort loves school, demonstrates academic growth, and develops the character and life skills necessary to succeed.
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 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 terminations
- Hands-on experience working with youth aged 5-18 in an educational or developmental context
- Experience building, launching, or substantially scaling a program, team, school, or outdoor initiative from inception, with a concrete and measurable example
- Documented use of data and metrics to establish objectives and inform decisions, beyond simply tracking outcomes
- Authorized to work legally in the United States
- Master's degree in a relevant discipline
- Background coaching athletics, leading wilderness or experiential education programs, directing camps, or managing youth programs at a scale requiring cohort management and outcome measurement
- Transitioned from classroom teaching to program leadership roles in EdTech, tutoring, youth-focused nonprofits, or school intervention teams
- Record of exceptional personal performance early in your career—academic, athletic, or professional—prior to entering leadership
- Conviction that the traditional education system is fundamentally flawed and a personal commitment to transforming 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-RoundRoc-OutdoorEducati
Salary : $150,000