Job Description
• Dripping Springs, TX (near Austin): full-time, on-site position
• $100,000 annually, paid weekly; comprehensive health, dental, and vision benefits from day one
• Relocation assistance provided
The most meaningful way to support a student in difficulty is to maintain high expectations. If that principle resonates with you — and if you would rather demonstrate it through field-based cohort work than classroom discussion — this role deserves your attention.
This position diverges from traditional teaching. Waypoint Academy students do not learn through seated instruction. They progress through adaptive learning technology at individualized speeds while you provide coaching in concentration, perseverance, and objective achievement. Your work extends outdoors: leading one-hour life-skills sessions covering public speaking, collaboration, leadership, and critical thinking through adventure-based experiential methods designed to be authentically challenging and engaging. Every session concludes with a Test2Pass mastery assessment — students apply the target skill in real scenarios before completion.
Your remaining hours center on motivation sessions: brief, one-on-one coaching interactions informed by Coachbot analytics, where you engage students and guide them toward their academic objectives. You will observe measurable, immediate transformation as students shift from disengaged learners to self-assured achievers. Your performance metrics are transparent: student satisfaction scores (90% benchmark) and weekly goal completion rates (100% benchmark).
High achievers advance to senior coaching positions: overseeing teams and influencing student motivation and development strategies. Beyond that lies complete school leadership — accountability for outcomes, culture, and operations. Dripping Springs sits 30 minutes from Austin's technology hub, live music venues, and culinary scene, offering 300+ days of sunshine and year-round Hill Country outdoor recreation.
If your career has been guided by the conviction that more effective methods exist for engaging young people, submit your application now.
What You Will Be Doing
• Facilitating 1-hour outdoor life-skills sessions (public speaking, concentration, leadership, collaboration) through nature-based adventure activities following Waypoint's curriculum and instructional playbook
• Conducting individual motivation sessions with students, leveraging Coachbot analytics and student profile information to guide them toward weekly academic objectives
• Completing each session with a Test2Pass mastery assessment: students apply the targeted life skill in authentic context before concluding
• Exercising outdoor safety protocols before every session: evaluating routes and weather conditions, inspecting equipment, and implementing Leave No Trace principles according to Waypoint's field standards
• Animating sessions through narrative techniques, creative adaptation, and the presence required to maintain engagement from K-12 cohorts in indoor and outdoor environments
What You Won’t Be Doing
• Conducting academic lectures or traditional board instruction. Students acquire content knowledge through adaptive educational technology; your function is coaching through obstacles, not content delivery.
• Supervising students during computer-based learning. Your focus is actively leading outdoor sessions, conducting motivation meetings, and coaching students through challenges.
• Evaluating assignments, creating original lesson plans, or preparing students for standardized examinations.
• Reducing expectations for students facing difficulties. Goals remain rigorous, mastery defines the standard, and your responsibility is coaching students to success — not adjusting requirements.
• Handling parent correspondence or administrative school functions. These duties fall under the Campus Lead's purview.
Experiential Education Facilitator Key Responsibilities
Support K-12 students at Waypoint Academy in developing enthusiasm for education, accelerating learning outcomes, and acquiring enduring life skills.
Basic Requirements
• Bachelor's degree in any discipline
• Minimum 3 years of direct experience with K-12 students in educational, camp, coaching, or outdoor instruction environments
• Documented history of exceptional personal accomplishment: competitive sports participation, academic distinction, or elite-level professional results
• Persuasive public speaker capable of energizing and sustaining attention from large student groups in both indoor and outdoor settings
• Innate capacity to engage K-12 learners as an aspirational role model who challenges their development, not a peer who accepts underperformance
• Authorization to work in the United States without requiring visa sponsorship
• Available for in-person work at the Waypoint Academy campus located in Dripping Springs, TX (near Austin)
Nice-to-have Requirements
• Background as an athletic coach, outdoor expedition leader, camp director, or wilderness education instructor
• Current first aid or wilderness safety credentials
• Knowledge of adaptive learning systems such as Khan Academy or IXL
• Experience in youth development, experiential education, or outdoor youth program delivery
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 $50 USD/hour, which equates to $100,000 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-5666-US-Houston-ExperientialEd.001
