Experiential Education Facilitator $100,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
- Dripping Springs, TX (near Austin): full-time, on-site position
- $100,000 annual salary, paid each week; health, dental, and vision coverage begins day one
- Relocation assistance provided
The best way to support a child who is struggling is to keep expectations high. If that resonates with you — and if you'd rather prove it by leading a group into the field than discussing it in a classroom — read on.
This is not traditional teaching. At Waypoint Academy, students don't absorb information from lectures while seated in rows. Instead, they progress through adaptive learning software at their own speed while you coach them on persistence, focus, and reaching their objectives. You'll bring them outdoors: one-hour life-skills sessions covering leadership, public speaking, problem-solving, and teamwork, delivered through adventure-based, experiential methods designed to be both challenging and engaging. Every session concludes with a Test2Pass mastery check — students must demonstrate the target skill in context before completion.
The remainder of your week centers on motivation sessions: brief, one-on-one coaching conversations informed by Coachbot analytics, where you engage with students and guide them toward their academic targets. You'll observe students evolve from hesitant learners into self-assured achievers — visibly and quickly. Your performance metrics are transparent: student satisfaction ratings (90% goal) and weekly objective completion (100% goal).
High performers advance into senior coaching positions: leading a team and influencing how the school motivates and develops its students. Beyond that lies full school ownership — accountability for outcomes, culture, and operations. Dripping Springs sits 30 minutes from Austin's technology hub, live music venues, and culinary landscape, offering 300+ days of sunshine and year-round Hill Country outdoor opportunities.
If you've always known there's a more effective way to connect with students, apply today.
What you will be doing
- Facilitating 1-hour outdoor life-skills sessions (leadership, public speaking, teamwork, focus) through adventure-style, nature-based activities following Waypoint's playbook and curriculum
- Conducting motivation sessions with students individually, leveraging Coachbot analytics and student profile information to guide them toward their weekly academic targets
- Ending every workshop with a Test2Pass mastery check: students must demonstrate the targeted life skill in authentic context before the session concludes
- Exercising outdoor safety judgment ahead of each session: assessing routes and weather, checking gear, and following Leave No Trace principles according to Waypoint's field guidelines
- Animating sessions through storytelling, creative adaptation, and the enthusiasm needed to maintain engagement from a K-12 cohort both indoors and outdoors
What you will NOT be doing
- Teaching academic content or presenting at a whiteboard. Students acquire course material through adaptive EdTech software; your role is to coach them past obstacles, not teach curriculum.
- Supervising students on devices. You'll be actively leading outdoor workshops, conducting motivation sessions, and coaching students who are facing challenges.
- Grading assignments, creating lesson plans from the ground up, or preparing students for standardized assessments.
- Reducing expectations for a struggling student. Goals remain real, mastery is the expectation, and your responsibility is to coach students across the finish line — not relocate it.
- Handling parent communications or school administration. These duties fall to the Campus Lead.
Key responsibilities
Support K-12 students at Waypoint Academy to love school, accelerate their learning, and develop enduring life skills.
Candidate requirements
- Bachelor's degree in any discipline
- Minimum 3 years of direct experience working with K-12 students in educational, camp, coaching, or outdoor education environments
- Documented history of high personal achievement: elite professional performance, academic honors, or competitive athletics
- Strong public speaker capable of energizing and maintaining attention from large student groups, both indoors and outdoors
- Innate ability to relate to K-12 learners as a positive role model who challenges them to develop, not as a peer who excuses underperformance
- Legal authorization to work in the U.S. without requiring visa sponsorship
- Available to work in-person at the Waypoint Academy campus in Dripping Springs, TX (near Austin)
Nice to have
- Background as an athletic coach, camp director, outdoor trip leader, or wilderness program instructor
- Wilderness safety or first aid certification
- Experience with adaptive learning platforms such as IXL or Khan Academy
- Experience in outdoor youth programming, experiential education, or youth development
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