Experiential Education Facilitator, Waypoint Academy

• Location: Dripping Springs (Austin area), TX (on‑campus)
• Compensation: $100,000 per year, paid weekly
• Benefits: Full health, dental, and vision coverage from day one
• Relocation: Assistance provided if needed

Waypoint Academy has eliminated traditional lectures in favor of adventure‑driven life skills development and AI‑powered personalized academics. Students don’t remain seated while you present—they develop public speaking competence on outdoor trails, cultivate leadership during team‑based challenges, and progress at twice the standard pace through adaptive learning technology.

This role is not conventional teaching. You will coach K‑12 students toward discovering their capabilities via outdoor workshops and motivational goal‑setting sessions. Your focus will be facilitating nature‑based experiences that develop tangible skills (concentration, communication, collaboration), rather than delivering standard curriculum. High‑caliber professionals who envision a fundamentally reimagined education model excel in this environment. You will observe measurable, immediate transformation as students shift from hesitant learners to self‑assured achievers.

Dripping Springs provides Hill Country scenery 30 minutes from Austin’s technology hub, live music venues, and culinary landscape. Over 300 sunny days annually, Barton Springs access, and year‑round outdoor opportunities.

Coach transformative growth. Facilitate adventure‑based learning. Submit your application today.

• Facilitating 1‑hour outdoor life‑skills workshops (public speaking, concentration, leadership, collaboration) via nature‑based challenges and adventure‑oriented activities.
• Conducting brief, high‑intensity motivation sessions coaching students toward academic targets using adaptive software platforms.
• Animating curriculum through storytelling, personalization, and dynamic energy that sustains K‑12 student engagement.
• Implementing safety protocols and outdoor decision‑making (route planning, weather assessment, gear inspection, Leave No Trace principles) according to Waypoint’s field standards.
• Evaluating skill acquisition as students demonstrate real‑world application of life skills.
• Maintaining rigorous standards of excellence while serving as an approachable, motivating role model 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 exceptional achievement (academic, athletic, or professional).
• Strong public speaking capability with the ability to energize and sustain attention across large student groups, both indoors and outdoors.
• Authentic capacity to connect with K‑12 learners, their interests, and culture—not as a peer but as an inspiring role model who challenges them toward growth.
• Legal authorization to work in the United States without requiring visa sponsorship.
• Commitment to on‑site work 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.