Outdoor Education Coach, Waypoint Academy

Waypoint Academy is redefining education by combining adventure-based life skills instruction with adaptive AI-driven academics. Students don’t stay seated listening to traditional lectures—they develop public speaking abilities on outdoor trails, cultivate leadership through collaborative challenges, and advance academically at 2× speed using personalized learning technology.

• On-campus position in Dripping Springs (Austin region), TX
• $100,000 annual compensation, paid weekly. Full health, dental, and vision coverage from day one
• Relocating? We provide relocation assistance

This role is about coaching K-12 students, not traditional teaching. You’ll guide them toward discovering their capabilities through hands‑on outdoor workshops and motivational goal‑setting sessions. You’ll facilitate nature‑based activities that develop tangible skills (concentration, communication, collaboration), rather than delivering standard curriculum. High achievers who envision a radically reimagined school environment excel in this position. You’ll witness measurable, immediate transformation as students shift from hesitant learners to self‑assured achievers.

Dripping Springs provides stunning Hill Country scenery just 30 minutes from Austin’s thriving tech ecosystem, renowned live music, and culinary scene. With over 300 sunny days annually, access to Barton Springs, and year‑round outdoor opportunities, it’s the perfect backdrop for transformative learning.

• Facilitating 1‑hour outdoor life‑skills workshops (leadership, public speaking, concentration, teamwork) using nature‑based challenges and adventure‑oriented activities
• Conducting brief, high‑energy motivation sessions where you guide students toward achieving academic targets through adaptive software platforms
• Transforming curriculum into engaging experiences through storytelling, personalization, and dynamic energy that sustains K‑12 student engagement
• Implementing safety procedures and outdoor decision‑making (route selection, weather monitoring, equipment inspection, Leave No Trace principles) following Waypoint’s field standards
• Evaluating skill acquisition by having students demonstrate their ability to apply life skills in authentic situations
• Maintaining high performance expectations while serving as an approachable, motivating mentor students genuinely admire

• Bachelor’s degree in any field
• At least 3 years of hands‑on experience with K‑12 students in educational, camp, coaching, or outdoor program settings
• Demonstrated history of exceptional achievement (academic, athletic, or professional)
• Strong public speaking skills with the ability to captivate and maintain the attention of large student groups, both indoors and outdoors
• Authentic capacity to connect with K‑12 learners, their interests, and their world—not as a peer but as a positive mentor who challenges them to develop
• Legal authorization to work in the United States without requiring visa sponsorship
• Commitment to working on‑site at Waypoint Academy’s Dripping Springs, TX campus (Austin area)

• First aid or wilderness safety certification

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!

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  for more details on this topic.

Crossover Job Code: LJ-5666-US-Dallas-Outdoor Educati.
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