What are the responsibilities and job description for the Experiential Education Facilitator, Waypoint Academy - $100,000/year USD position at Crossover?
- Dripping Springs, TX (near Austin): full-time, on-site
- $100,000 annually, paid weekly; comprehensive health, dental, and vision coverage from day one
- Relocation assistance provided
This is not traditional teaching. Students at Waypoint Academy do not sit in classroom rows taking notes from a board. They progress through adaptive learning technology at their own rate while you coach them on persistence, focus, and achieving their goals. You will take them outdoors: facilitating one-hour experiential life-skills sessions on leadership, public speaking, problem-solving, and teamwork, using adventure-based activities designed to challenge and engage. Every session ends with a Test2Pass mastery demonstration — students show they can apply the skill in real context before the workshop concludes.
The remainder of your schedule is dedicated to motivation sessions: brief, one-on-one coaching conversations informed by Coachbot analytics, where you connect with individual students and help them advance toward academic milestones. You will see students shift from disengaged learners to self-assured performers — visibly and quickly. Your performance metrics are transparent: student satisfaction scores (90% benchmark) and weekly goal completion rates (100% benchmark).
High performers advance into senior coaching positions: leading a team and influencing how the school drives student motivation and growth. Beyond that lies full school leadership — accountability for outcomes, culture, and operations. Dripping Springs sits 30 minutes from Austin's technology sector, live music venues, and culinary scene, offering over 300 sunny days annually and year-round access to Hill Country recreation.
If you have long believed there is a more effective way to reach young people, apply today.
What You Will Be Doing
- Facilitating 1-hour outdoor life-skills sessions (leadership, public speaking, teamwork, focus) through adventure-based, nature-centered activities following Waypoint's curriculum and operational playbook
- Conducting motivation sessions with individual students, leveraging Coachbot analytics and student data to guide them toward weekly academic objectives
- Concluding each session with a Test2Pass mastery assessment: students apply the targeted life skill in authentic context before the workshop closes
- Exercising outdoor safety protocols before every session: evaluating routes and weather, performing gear inspections, and following Leave No Trace principles per Waypoint's field standards
- Animating sessions through storytelling, creative adaptation, and the presence required to maintain engagement from K-12 learners both indoors and outdoors
- Presenting academic lectures or teaching from a whiteboard. Students engage with course material through adaptive EdTech platforms; your focus is coaching them past obstacles, not delivering subject content.
- Supervising students passively on computers. You will be actively running outdoor workshops, leading motivation sessions, and coaching students who need help.
- Evaluating assignments, creating lesson plans from the ground up, or preparing students for standardized exams.
- Reducing expectations for a struggling student. Standards remain firm, mastery is non-negotiable, and your responsibility is to coach students to meet the mark — not adjust it.
- Handling parent outreach or administrative duties. Those functions are the responsibility of the Campus Lead.
Support K-12 students at Waypoint Academy to enjoy learning, accelerate their academic progress, and develop durable life skills.
Basic Requirements
- Bachelor's degree in any field
- Minimum 3 years of direct experience working with K-12 students in educational, camp, coaching, or outdoor instruction environments
- Documented history of high personal achievement: competitive sports, academic distinction, or exceptional professional accomplishment
- Strong public speaking ability with the capacity to energize and sustain 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 improve, rather than a peer who accepts underperformance
- Authorization to work in the U.S. without requiring visa sponsorship
- Availability to work on-site at the Waypoint Academy campus in Dripping Springs, TX (near Austin)
- Experience serving as an athletic coach, outdoor expedition leader, camp director, or wilderness program facilitator
- Wilderness safety or first aid credentials
- Knowledge of adaptive learning systems such as Khan Academy or IXL
- Experience in youth development, experiential education, or outdoor programming for young people
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
Salary : $100,000