What are the responsibilities and job description for the Youth Development Director, Waypoint Academy - $150,000/year USD position at Crossover?
- On-site role at Waypoint Academy, Dripping Springs, Texas
- $150,000 annually, W2 employee status, weekly pay. Health coverage begins day one.
- Relocation assistance provided
Waypoint Academy runs core academics through self-paced, AI-driven adaptive platforms that consolidate formal instruction into a concentrated morning block. No classroom lectures. That structure opens up your schedule for the work that genuinely shifts a student's path. A typical morning might begin with a coaching debrief alongside 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 real obstacles. Afternoons are reserved for individual motivation work: sitting down with students, understanding what fuels them, and moving disengaged learners toward ownership of their goals. You maintain your own cohort throughout, keeping your coaching grounded in live experience.
You've likely been the outlier in traditional education: overly analytical, excessively outcome-oriented, too quick to take students into the field and let them wrestle with difficulty. This may be the first environment that values exactly that. You begin coaching fellow Guides immediately, and as your results become visible, the standard you establish spreads across the cohort and your scope of influence expands. You'll witness the impact firsthand: a doubtful student who begins to take ownership, a Guide who sharpens because you gave direct feedback, a young person who emerges from the wilderness more confident and capable.
Uphold the standard. Get them outside. Submit your application.
What You Will Be Doing
- Provide coaching to the Guides on your team: analyze performance metrics, observe their interactions with students, and conclude every session with clear, actionable next steps that address performance gaps.
- Facilitate one-hour outdoor life-skills workshops where students from K-12 develop leadership, grit, collaboration, and communication skills through adventure-based activities.
- Conduct motivation sessions that leverage student analytics and Coachbot insights to propel every student toward goal achievement and personal accountability.
- Maintain your own student cohort while simultaneously developing other Guides, ensuring your coaching stems from active practice rather than past experience.
- Monitor student satisfaction scores, goal attainment rates, and Guide performance metrics on a weekly basis to identify and address underperformance early.
- Delivering lectures or providing academic tutoring. Students progress through self-directed adaptive technology, frequently without direct adult instruction.
- Creating curriculum or designing lesson plans. Established frameworks are in place; your focus is on execution quality and engagement, not innovation.
- Training Guides on instructional pedagogy. Since Guides do not lecture, your coaching centers on motivation tactics, accountability systems, and interpersonal presence.
- Compromising standards to avoid conflict. You will not advance a student prematurely or overlook underperformance among Guides.
- Confining students to indoor, seated learning. A significant portion of development at Waypoint occurs outdoors through experiential challenge.
Ensure that every student in your cohort develops a genuine love for school, demonstrates academic growth, and acquires the character and practical 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 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 at least 5 adults, including responsibility for hiring and performance-based termination decisions
- Hands-on experience working with youth ages 5-18 in educational or developmental contexts
- Experience building, launching, or substantially scaling a program, team, school, or outdoor initiative from inception, with a concrete and measurable outcome
- Documented use of data and performance metrics to establish objectives and inform decision-making, beyond simple reporting
- Legal authorization to work in the United States
- Master's degree in a relevant field
- Background coaching athletics, leading wilderness or experiential education programs, managing camps, or directing youth initiatives at a scale requiring cohort management and outcome tracking
- Transitioned out of classroom teaching to develop or lead programs in a different capacity: EdTech, tutoring services, youth-focused nonprofits, or school intervention initiatives
- Strong early-career performance record—academic, athletic, or professional—prior to stepping into leadership roles
- Conviction that conventional education systems are inadequate and personal commitment to reforming them
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-YouthDevelopme
Salary : $150,000