Learning Instructor, Waypoint Academy

On-site position in Dripping Springs (Austin area), TX. $100,000 annual salary, paid weekly. Health, dental, and vision benefits begin on day one. Relocation assistance available for candidates who need to move.

Waypoint Academy is replacing traditional classroom instruction with adventure-driven life skills training and AI-powered personalized academics. Instead of sitting through lectures, students develop public speaking skills outdoors, cultivate leadership through collaborative challenges, and progress at twice the typical pace using adaptive learning technology.

This role is about coaching, not teaching. You will guide K‑12 students toward realizing their capabilities through hands‑on outdoor workshops and motivational goal‑setting sessions. Your focus will be facilitating nature‑based experiences that develop tangible skills—focus, communication, teamwork—rather than delivering standard curriculum. High‑performing individuals who envision a fundamentally different model of education excel in this environment. You will witness measurable, immediate transformation as students shift from disengaged learners to self‑assured achievers.

Dripping Springs provides Hill Country scenery just 30 minutes from Austin's technology hub, live music venues, and culinary offerings. The area enjoys over 300 sunny days annually, access to Barton Springs, and year‑round outdoor recreation.

• Facilitating 1‑hour outdoor life‑skills sessions (public speaking, focus, leadership, teamwork) through nature‑based challenges and adventure‑style programming.
• Conducting brief, high‑energy motivational sessions that coach students toward academic targets using adaptive learning software.
• Delivering curriculum with storytelling, personalization, and dynamic energy to maintain high engagement among K‑12 students.
• Implementing safety protocols and outdoor risk management (route planning, weather monitoring, equipment checks, Leave No Trace principles) according to Waypoint's operational standards.
• Evaluating skill acquisition by having students demonstrate real‑world application of the life skills they've learned.
• Setting a high standard of excellence while serving as an inspiring, approachable role model students genuinely admire.

• Bachelor's degree in any discipline.
• At least 3 years of experience working 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 the capacity to energize and maintain attention from large student groups, both indoors and outdoors.
• Innate capacity to connect with K‑12 learners, their interests, and cultural context—not as a peer, but as a positive role model who challenges them to improve.
• Legal authorization to work in the United States without requiring visa sponsorship.
• Availability to work on‑site at Waypoint Academy's Dripping Springs, TX campus (near Austin).

• First aid or wilderness safety certification.

Nature‑based school that blends rigorous academics with real‑world challenges.

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-Phoenix-Adventure Learn.
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