Outdoor Education Coach, Waypoint Academy

Overview

Waypoint Academy has replaced traditional classroom lectures with adventure-driven life skills training and AI-powered personalized academics. Students develop public speaking abilities on outdoor trails, cultivate leadership through group challenges, and progress at a faster pace using adaptive learning technology. This role is about coaching, not conventional teaching. You will guide K-12 students toward discovering their capabilities through outdoor experiential workshops and motivational coaching sessions.

You will facilitate nature-based activities that develop concrete skills—focus, communication, teamwork—rather than deliver standard curriculum. High-performing individuals who are convinced that education needs fundamental transformation 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. Over 300 sunny days annually, access to Barton Springs, and year-round outdoor recreation.

Guide their growth. Lead the adventure. Apply today.

• Facilitating 1-hour outdoor life-skills workshops (public speaking, focus, leadership, teamwork) using nature-based challenges and adventure-style programming
• Conducting brief, high-energy motivational coaching sessions where you guide students toward achieving academic targets with adaptive software tools
• Making curriculum engaging through storytelling, personalization, and dynamic delivery that maintains high engagement among K-12 students
• Implementing safety protocols and sound outdoor judgment (route planning, weather assessment, equipment checks, Leave No Trace principles) following Waypoint's field standards
• Evaluating skill acquisition by having students demonstrate real-world application of the life skills they've learned
• Maintaining rigorous standards of excellence while serving as an approachable, motivating role model whom students genuinely respect and admire

• Bachelor's degree in any subject
• Minimum 3 years of experience working with K-12 students in school, camp, coaching, or outdoor programs
• Proven track record of high achievement (academically, athletically, or professionally)
• Compelling public speaker who can energize and hold attention for large groups of students, indoors and outdoors
• Natural ability to relate to K-12 learners, their interests, and culture, not as a "buddy" but as a positive role model who pushes them to grow
• Legal right to work in the United States without visa sponsorship
• Willingness to work in-person at Waypoint Academy's campus in Dripping Springs, TX (near Austin)

• First aid or wilderness safety training

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.

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