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

Based on-site at Waypoint Academy, Dripping Springs, Texas $150,000 annual salary as W2 employee with weekly pay. Health benefits start day one. Relocation assistance provided Based on-site at Waypoint Academy, Dripping Springs, Texas $150,000 annual salary as W2 employee with weekly pay. Health benefits start 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 premise unsettles you, this role isn't for you. If you agree, read on. Waypoint Academy delivers core academics through self-directed, AI-driven adaptive platforms that condense traditional instruction into a focused morning block. No classroom lectures. That design liberates your schedule for the interventions that genuinely alter student outcomes. You might begin your morning reviewing cohort analytics one-on-one with a Guide, identifying patterns where students are losing momentum. By late morning, you're outside facilitating experiential workshops that develop resilience and collaboration through structured challenge. Afternoons are dedicated to individual motivation work: understanding what drives each student and converting hesitation into forward motion. You carry your own student cohort throughout, ensuring the skills you coach remain grounded in daily practice. You've likely been the outlier in traditional education: overly focused on outcomes, excessively reliant on data, too inclined to push students into discomfort and growth. This may be the first environment designed for you. You begin coaching fellow Guides immediately, and as your results compound, the benchmark you establish influences the broader cohort and your authority within the program expands. You witness impact directly: the skeptical student who begins taking ownership, the Guide whose performance sharpens after candid feedback, the young person who emerges from outdoor challenges visibly more capable. Uphold the standard. Lead them outside. What You Will Be Doing Provide direct coaching to Guides: analyze performance metrics, observe their interactions with students, and conclude each session with concrete improvement steps. Facilitate one-hour experiential outdoor workshops where students in grades K-12 develop leadership, communication, teamwork, and resilience through adventure-based activities. Conduct individualized motivation sessions informed by analytics and Coachbot insights to drive every student toward goal ownership and measurable progress. Maintain responsibility for your own student cohort while simultaneously developing other Guides, ensuring your coaching reflects active practice rather than past experience. Monitor weekly metrics on student satisfaction, goal attainment, and Guide effectiveness to identify and address underperformance early. What You Won’t Be Doing Delivering lectures or academic tutoring. Students engage with content via self-paced adaptive technology, frequently without direct adult supervision. Creating original curriculum or developing lesson plans. Established frameworks are in place; success depends on consistent execution and engagement, not innovation. Training Guides on instructional methods. Since Guides do not teach traditionally, your coaching centers on motivation, accountability, and interpersonal presence. Compromising standards for convenience. You will not advance underperforming students or overlook insufficient Guide performance. Confining students to indoor spaces. A significant portion of developmental work occurs outdoors through experiential challenges. Youth Program Director Key Responsibilities Ensure that every student in your cohort develops a positive relationship with school, achieves measurable academic growth, and acquires the character and life skills necessary for long-term success. Basic Requirements Available 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' experience in education, youth development, coaching, outdoor education, or learning and development (L&D) Demonstrated leadership of a team of 5 or more adults, with direct responsibility for hiring and performance-based termination Hands-on experience working with youth ages 5-18 in educational or developmental contexts Evidence of building, launching, or scaling a program, team, school, or outdoor initiative from inception, supported by a concrete, measurable outcome Documented experience using data and metrics to inform goal-setting and decision-making, beyond simple reporting Legal authorization to work in the United States Nice-to-have Requirements Master's degree in a relevant discipline Background in athletic coaching, wilderness/experiential education, camp direction, or large-scale youth programs involving cohort management and outcome measurement Transitioned from classroom teaching into program leadership roles in EdTech, tutoring organizations, youth nonprofits, or school intervention teams Early-career record of exceptional individual performance—academic, athletic, or professional—prior to entering leadership Strong conviction that conventional education systems are inadequate and personal commitment to systemic redesign 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. 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 for more details on this topic. #J-18808-Ljbffr Crossover