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

On-site role at Waypoint Academy, Dripping Springs, Texas $150,000 annual salary as a W2 employee with weekly pay. Health benefits begin day one. Relocation assistance provided The greatest support you can offer a young person is to place a challenge in front of them and resist the urge to carry it for them. If that philosophy troubles you, this isn't the right fit. If it resonates, read on. Waypoint Academy runs core academics through self‑paced, AI‑driven adaptive platforms that consolidate the school day into a concentrated morning block. There are no traditional lectures. This structure liberates your time for the work that genuinely shifts a student's path. You might start your morning in a one‑on‑one strategy session with a Guide, analyzing student metrics to identify where a group is faltering. By midday, you're outside facilitating a hands‑on workshop that builds teamwork and grit through authentic struggle. Afternoons are dedicated to motivational coaching: meeting individually with students, uncovering what inspires them, and mobilizing a reluctant learner toward meaningful goals. You maintain your own student cohort throughout, ensuring the competencies you develop in others remain grounded in current practice. You've likely been the outlier in traditional education: too metric‑oriented, too outcome‑focused, too comfortable taking students outdoors and allowing them to grapple with difficulty. This could be the first environment that truly aligns. You'll mentor other Guides from the outset, and as your results compound, the benchmark you establish influences the entire cohort and your authority within the program expands. The impact is tangible and immediate: a doubtful student who begins to claim their own development, a Guide who sharpens because you offered candid feedback, a young person who emerges from the woods more resilient than when they entered. What You Will Be Doing Mentor the Guides working with you: analyze performance metrics, observe their interactions with students, and conclude each session with targeted actions that address identified gaps. Facilitate one‑hour outdoor life‑skills workshops where students in grades K‑12 develop leadership, grit, collaboration, and communication through adventure‑based activities. Conduct motivational coaching sessions informed by student analytics and Coachbot insights to activate every learner toward their objectives and cultivate ownership of their progress. Maintain your own student cohort while guiding other educators, ensuring your coaching is rooted in present experience rather than past recollection. 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 via self‑directed adaptive platforms, frequently without direct adult supervision. Creating curriculum or lesson plans from the ground up. Established playbooks are in place; success depends on faithful execution and engagement, not innovation. Training Guides on instructional methods. Since Guides don't lecture, your coaching focuses on motivation, accountability, and relational presence with students. Compromising standards to preserve comfort. You won't advance a student prematurely or overlook a Guide's lack of performance. Confining students indoors to desks. A substantial portion of development here occurs outside, through experiential challenge. Youth Program Director Key Responsibilities Ensure that every student in your cohort loves school, achieves 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 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 leading a team of 5 or more adults, including making 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 growing 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 simply to report outcomes Legal authorization to work in the United States Nice‑to‑have Requirements Master's degree in a relevant field Experience 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 manage programs in a different capacity: EdTech, tutoring, youth nonprofits, or school intervention teams Early‑career history of exceptional personal performance—academic, athletic, or professional—prior to entering leadership Conviction that the conventional education model is fundamentally flawed and personal commitment to its transformation About Waypoint Academy Nature‑based school that blends rigorous academics with real‑world challenges. 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