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Experiential Education Facilitator, Waypoint Academy - $100,000/year USD

Crossover, Dripping Springs, Texas, United States, 78620

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Overview Waypoint Academy has eliminated traditional lecture-based instruction in favor of adventure-driven life skills development and AI-powered adaptive academics. Students do not remain seated while you present information — they develop public speaking abilities on outdoor trails, cultivate leadership competencies through collaborative challenges, and progress at twice the typical pace using individualized software platforms.

This role is about coaching K-12 learners to unlock their capabilities through experiential outdoor sessions and motivational goal-setting—not delivering standardized curriculum. You will facilitate nature-centered activities that cultivate tangible skills: focus, communication, and collaboration. High-performing individuals who believe conventional schooling requires fundamental transformation excel in this environment. You will observe measurable, immediate shifts as students evolve from disengaged learners into self-assured, capable achievers.

Dripping Springs combines Hill Country natural beauty with proximity to Austin's vibrant technology sector, live music venues, and culinary offerings—all within 30 minutes. The region enjoys over 300 sunny days annually, Barton Springs access, and year-round outdoor recreation.

Guide the transformation. Lead the experience. Submit your application today.

What You Will Be Doing

Facilitating 1-hour outdoor life-skills sessions (public speaking, focus, leadership, teamwork) via nature-centered challenges and adventure-oriented activities

Conducting brief, results-focused motivational sessions where you guide students toward achieving academic objectives using adaptive software platforms

Animating curriculum through storytelling, tailored approaches, and dynamic energy that sustains high engagement among K-12 learners

Implementing safety protocols and field judgment (route selection, weather evaluation, equipment inspection, Leave No Trace fundamentals) according to Waypoint's operational guidelines

Evaluating skill acquisition by requiring students to demonstrate practical application of life skills in authentic scenarios

Maintaining rigorous standards of excellence while serving as an approachable, motivating role model whom students genuinely admire

Basic Requirements

Bachelor's degree in any field

At least 3 years of experience engaging with K-12 students through school settings, camps, coaching roles, or outdoor programs

Documented history of high achievement in academic, athletic, or professional domains

Strong public speaking capability with the ability to energize and sustain attention among large student groups in both indoor and outdoor environments

Innate capacity to connect with K-12 learners, understanding their interests and culture—not as a peer but as a constructive role model who challenges them to develop

Legal authorization to work in the United States without requiring visa sponsorship

Availability to work onsite at Waypoint Academy's campus in Dripping Springs, TX (near Austin)

Nice-to-have Requirements

First aid or wilderness safety certification

About Waypoint Academy 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!

Working with us 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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5666-US-Dripping-ExperientialEd.003

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