Youth Development Director, Waypoint Academy - $150,000/year USD

• In-person role based at Waypoint Academy, Dripping Springs, Texas
• Annual salary of $150,000 as a W2 employee with weekly pay. Health benefits begin on day one.
• Support for relocation provided

The best way to help a young person is to give them something difficult and let them carry it themselves. If that idea makes you uncomfortable, this isn't for you. If it resonates, read on.

Waypoint Academy runs core academics through self-directed, AI-driven adaptive platforms that condense the traditional school day into a concentrated morning block. There are no lectures. That design opens up your day for the work that genuinely shifts a student's path. Your mornings may begin with a one-on-one session alongside a Guide, analyzing student data to identify where a group is falling behind. By the middle of the day, you're outside facilitating a hands-on workshop that builds teamwork and resilience through authentic challenge. In the afternoon, you shift into motivation work: meeting individually with students, discovering what matters to them, and moving a reluctant learner closer to their own goals. You also carry your own cohort throughout, which keeps you grounded in the same work you're coaching others to do.

You've likely been the outlier in traditional education: too focused on data, too outcome-oriented, too comfortable taking students outdoors and letting them face difficulty. This may be the first environment where that approach is valued. You begin coaching other Guides immediately, and as you produce results, the standard you model extends across the entire cohort and your influence within the program deepens. The impact is visible in real time: a doubtful student who begins taking ownership of their learning, a Guide who sharpens their approach because you gave direct feedback, a young person who emerges from a field experience more capable than when they entered.

Uphold the standard. Get them outside. Apply now.

What You Will Be Doing

• Provide coaching to the Guides working with you: analyze performance data, observe their interactions with students, and conclude each session with clear, actionable steps to address 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 informed by student analytics and Coachbot data to ensure every student advances toward their goals and takes ownership of their progress.
• Maintain your own student cohort while mentoring other Guides, ensuring your coaching is rooted in active practice rather than past experience.
• Monitor student satisfaction, goal achievement, and Guide effectiveness on a weekly basis to identify and address underperformance early.

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring. Students engage with content through self-guided adaptive platforms, frequently with minimal adult supervision.
• Developing original curriculum or creating lesson plans. The frameworks are already in place; your focus is on consistent execution and energy, not innovation.
• Training Guides on instructional methods. Since Guides don't lecture, your coaching centers on motivation, accountability, and presence with students.
• Compromising standards to maintain harmony. You will not advance a student prematurely or overlook a Guide's lack of performance.
• Confining students to indoor, seated environments. A significant portion of the learning here takes place outdoors, through challenge-based experiences.

Youth Development Director 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.

Basic Requirements

• Able 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 experience leading a team of 5 or more adults, including responsibility for hiring and performance-based termination
• Hands-on experience working with young people aged 5-18 in an educational or developmental context
• History of building, launching, or scaling a program, team, school, or outdoor initiative from the ground up, with a concrete and measurable example
• Documented use of data and metrics to establish goals and inform decisions, not simply to report outcomes
• Legal authorization to work in the United States

Nice-to-have Requirements

• Master's degree in a related discipline
• Experience coaching athletics, leading wilderness or experiential education programs, managing camps, or directing youth programs at a scale requiring cohort management and outcome measurement
• Transitioned out of classroom teaching to build or lead programs in another capacity: EdTech, tutoring organizations, youth-focused nonprofits, or school intervention initiatives
• Strong record of personal achievement early in your career—academic, athletic, or professional—prior to moving into leadership roles
• Conviction that the conventional education system is ineffective and a personal commitment to transforming it

About Waypoint Academy 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-YouthDevelopme.005