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

In-person role at Waypoint Academy, Dripping Springs, Texas $150,000 annual salary as a W2 employee with weekly pay. Full health coverage begins day one. Relocation assistance provided In-person role at Waypoint Academy, Dripping Springs, Texas $150,000 annual salary as a W2 employee with weekly pay. Full health coverage begins day one. Relocation assistance provided The best way to support a young person is to give them something difficult and refuse to do it for them. If that idea unsettles you, this isn't the role. If it resonates, read on. Waypoint Academy structures core academics around self-directed, AI-driven adaptive platforms that condense the school day into a concentrated morning block. No traditional lectures. That structure frees you to focus on the work that genuinely shifts a student's path. Your morning may begin with a one-on-one session alongside a Guide, analyzing student performance data to identify where a group is falling behind. By midday, you're outside facilitating a hands-on workshop that builds teamwork and resilience through authentic challenge. Afternoons transition to motivation work: meeting individually with students, identifying what motivates them, and guiding a disengaged student toward meaningful goals. You maintain your own student cohort throughout, keeping your coaching grounded in live practice rather than past experience. You’ve likely been the outlier in education: excessively data-oriented, overly focused on outcomes, too ready to bring students outdoors and let them wrestle with difficulty. This may be the first environment where that approach fits. You begin coaching other Guides immediately, and as you produce results, the benchmark you establish influences the entire cohort and your leadership impact expands. You'll witness the outcome directly: a doubtful student who begins taking ownership of their development, a Guide who sharpens because you gave honest feedback, a young person who emerges from an outdoor challenge more competent than when they entered. Uphold the standard. Bring them outside. 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 actions that address performance gaps. Facilitate one-hour outdoor workshops focused on life skills, where K-12 students develop leadership, resilience, collaboration, and communication through adventure-based activities. Conduct motivation sessions leveraging student analytics and Coachbot insights to drive every student toward their objectives and personal accountability for progress. Maintain your own student cohort while mentoring other Guides, ensuring your coaching is rooted in active experience rather than recollection. Monitor student satisfaction, goal attainment, and Guide effectiveness on a weekly basis to identify underperformance early. What You Won’t Be Doing Delivering lectures or providing academic tutoring. Students engage with self-guided adaptive platforms, frequently without direct adult supervision. Creating curriculum or lesson frameworks from the ground up. Established playbooks are in place; execution with fidelity and energy is the expectation, not innovation. Training Guides in instructional methods. Guides do not lecture, so your coaching centers on motivation, accountability, and their 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 indoors and seated. A significant portion of learning at Waypoint occurs outside, through challenge-based experiences. Youth Program Director Key Responsibilities Ensure every student in your cohort develops a genuine love for school, demonstrates academic growth, and cultivates the character and life skills necessary for long-term success. 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 related discipline Minimum of 5 years 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 termination Hands-on experience working with youth aged 5-18 in an educational or developmental context Experience building, launching, or substantially expanding a program, team, school, or outdoor initiative from inception, with a concrete and measurable example Demonstrated application of data and metrics to establish goals and inform decision-making, not solely for reporting 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 programs, directing camps, or managing youth programs at a scale requiring cohort management and outcome measurement Transitioned from classroom teaching to program design or leadership in another capacity: EdTech, tutoring, youth nonprofits, or school intervention teams Early-career record of exceptional personal performance—academic, athletic, or professional—prior to entering leadership roles Conviction that the conventional education model is fundamentally flawed and personal commitment to redesigning it About Waypoint Academy Nature-based school that blends rigorous academics with real-world challenges. Working with us This is a full-time, W2 employee position with immediate access to benefits ( All roles are year-long positions. The compensation level for this role is $150,000 USD/year. The payment period is weekly. Consult for more details on this topic. Crossover Job Code: LJ-5818-US-Dripping-YouthProgramDi.008 #J-18808-Ljbffr Crossover