Experiential Education Facilitator, Waypoint Academy

• On-campus position in Dripping Springs (greater Austin region), TX
• $100,000 annual compensation, distributed weekly. Full health, dental, and vision coverage begins day one
• Considering a move? Relocation assistance provided

Waypoint Academy has eliminated traditional lecture-based instruction in favor of adventure-driven life skill development and AI-powered personalized academics. Instead of sitting in rows while an instructor talks, students learn public speaking on wilderness trails, develop leadership through collaborative challenges, and progress at twice the standard pace using tailored software.

This role is not conventional teaching. You will coach K-12 students to unlock their capabilities through outdoor facilitation and targeted goal-setting sessions. Your work centers on guiding nature-based experiences that cultivate tangible competencies—focus, communication, teamwork—rather than delivering prescribed lessons. High performers who are convinced traditional schooling must be reimagined will find purpose here. Student transformation from disengaged learners to self-assured achievers happens visibly and quickly.

Dripping Springs combines Hill Country natural beauty with proximity to Austin's technology hub, live music venues, and culinary landscape—just 30 minutes away. 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, focus, leadership, teamwork) using nature-based challenges and adventure-oriented activities
• Conducting brief, high-energy motivational sessions where you guide students toward academic milestones with adaptive software
• Animating curriculum through storytelling, personalization, and dynamic delivery that sustains K-12 student engagement
• Implementing safety procedures and outdoor decision-making (route planning, weather monitoring, equipment checks, Leave No Trace principles) according to Waypoint's field standards
• Evaluating skill acquisition by requiring students to demonstrate real-world application of life skills
• Maintaining a rigorous standard of excellence while serving as an approachable, motivating mentor students genuinely respect

• Bachelor's degree in any discipline
• At least 3 years of hands‑on experience with K-12 students in educational, camp, coaching, or outdoor program settings
• Documented history of high achievement (academic, athletic, or professional)
• Strong public speaking ability with the capacity to captivate and sustain attention among large student groups, both indoors and outdoors
• Innate skill in connecting with K-12 learners, understanding their interests and culture, while serving as a positive role model who challenges them to develop—not as a peer
• 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 vicinity)

• 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-Austin-Experiential Ed.
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