Outdoor Education Coach, Waypoint Academy

• On-campus position in Dripping Springs (Austin area), TX
• $100,000 annual salary, disbursed weekly. Full health, dental, and vision coverage begins day one
• Relocating? Relocation assistance provided

Waypoint Academy is redefining education by replacing conventional classroom instruction with adventure-driven life skills development and AI-powered personalized academics. Students move beyond passive desk learning—they develop public speaking skills in outdoor settings, cultivate leadership through collaborative challenges, and progress academically at twice the typical pace using intelligent adaptive technology.

This role is about coaching, not traditional teaching. You will guide K-12 students toward self-discovery through hands‑on outdoor workshops and focused motivational sessions. Your work centers on facilitating nature-based experiences that cultivate essential competencies—concentration, communication, collaboration—rather than delivering scripted lessons. High-caliber professionals who envision a fundamentally transformed school model excel in this environment. You will witness measurable, immediate transformation as students evolve from hesitant participants into self‑assured achievers.

Dripping Springs combines Hill Country natural beauty with proximity to Austin—30 minutes from the city's technology hub, renowned live music venues, and diverse culinary scene. Expect over 300 sunny days annually, access to Barton Springs, and year-round outdoor recreation.

Guide their development. Lead the experience. Apply today.

• Facilitating 1-hour outdoor life-skills sessions (public speaking, concentration, leadership, collaboration) using nature-based challenges and adventure-oriented activities
• Conducting focused, high-energy coaching sessions that help students achieve academic targets with adaptive software tools
• Animating curriculum through storytelling, personalization, and dynamic delivery that sustains K-12 student engagement
• Implementing safety standards and field judgment (route design, weather monitoring, equipment inspection, Leave No Trace principles) according to Waypoint's outdoor protocols
• Evaluating competency attainment by having students demonstrate life-skill application in authentic scenarios
• Maintaining elevated performance standards while serving as an approachable, motivating mentor students genuinely respect

• Bachelor's degree in any discipline
• Minimum 3 years of documented experience with K-12 students in educational, camp, coaching, or outdoor program settings
• Demonstrated history of high achievement (academic, athletic, or professional)
• Strong public speaking ability with proven capacity to energize and maintain attention across large student groups, both indoors and outdoors
• Authentic capacity to connect with K-12 learners, their interests, and their culture—not as a peer but as a credible role model who challenges them to develop
• Legal authorization to work in the United States without requiring visa sponsorship
• Commitment to working onsite at Waypoint Academy's campus in Dripping Springs, TX (near Austin)

• 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.