Outdoor Education Teacher, Waypoint Academy - $100,000/year USD

• Dripping Springs, TX (near Austin): full-time, on-site position
• $100,000 annually, paid weekly; health, dental, and vision coverage starting day one
• Relocation assistance provided
  
  

The greatest support you can offer a struggling student is maintaining high expectations. If that principle resonates with you — and if you'd prefer to demonstrate it by leading a group into the outdoors rather than presenting it in a classroom — continue reading.

This role diverges from traditional teaching. Waypoint Academy students don't attend conventional lectures seated in rows. They progress through adaptive learning software independently while you guide them on concentration, perseverance, and achievement. You'll take them outside for one-hour life-skills sessions: public speaking, teamwork, leadership, and problem-solving, delivered through adventure-based, experiential methods designed to be authentically challenging and engaging. Every session concludes with a Test2Pass mastery assessment — students must demonstrate the target skill in practical context to complete it.

Your remaining time centers on motivation sessions: brief, one-on-one coaching interactions informed by Coachbot analytics, connecting with students and advancing them toward their academic objectives. You'll observe students shift from hesitant learners to self-assured achievers — measurably and quickly. Your performance metrics are transparent: student satisfaction scores (90% goal) and weekly objective completion (100% goal).

High achievers advance to senior coaching positions: leading a team and influencing the school's approach to student motivation and development. Beyond that lies full school leadership — accountability for outcomes, culture, and operations. Dripping Springs sits 30 minutes from Austin's technology hub, live music venues, and dining scene, offering 300 days of sunshine and year-round Hill Country outdoor recreation.

If you've long believed there's a more effective way to engage students, submit your application today.

What You Will Be Doing

• Facilitating 1-hour outdoor life-skills sessions (public speaking, focus, leadership, teamwork) through nature-based, adventure-style programming using Waypoint's established curriculum and playbook
• Conducting individual student motivation sessions, leveraging Coachbot analytics and student profile information to guide them toward weekly academic targets
• Concluding every workshop with a Test2Pass mastery assessment: students must demonstrate the specific life skill in authentic context before the session is complete
• Exercising outdoor safety judgment prior to each session: evaluating routes and weather conditions, conducting gear inspections, and adhering to Leave No Trace principles per Waypoint's field protocols
• Energizing sessions through narrative, creative adaptation, and the presence required to maintain engagement from a K-12 learner cohort both indoors and outdoors
  
  

What You Won’t Be Doing

• Presenting academic lectures or teaching from the front of a classroom. Students master academic content via adaptive EdTech software; your function is coaching them through obstacles, not delivering curriculum.
• Supervising students at computer stations. You'll actively lead outdoor workshops, conduct motivation sessions, and support students who are facing challenges.
• Evaluating assignments, creating original lesson plans, or preparing students for standardized assessments.
• Reducing expectations for struggling students. Goals remain rigorous, mastery is the benchmark, and your responsibility is coaching students to success — not adjusting standards.
• Handling parent correspondence or administrative duties. These tasks are the Campus Lead's responsibility.
  
  

Outdoor Education Teacher Key Responsibilities

Support K-12 students at Waypoint Academy to develop enthusiasm for school, accelerate their learning, and acquire enduring 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 education environments
• Documented history of exceptional personal achievement: competitive sports, academic distinction, or high-level professional accomplishment
• Effective public speaker capable of engaging and sustaining attention from large student groups, both indoors and outdoors
• Innate capacity to relate to K-12 learners as an inspiring role model who challenges them to advance, not as a peer who accepts mediocrity
• Legal authorization to work in the United States without requiring visa sponsorship
• Available to work in-person at the Waypoint Academy campus located in Dripping Springs, TX (near Austin)
  
  

Nice-to-have Requirements

• Background as an athletic coach, outdoor expedition leader, camp director, or wilderness program facilitator
• Wilderness safety or first aid certification
• Knowledge of adaptive learning platforms like Khan Academy or IXL
• Experience in youth development, experiential education, or outdoor youth programming
  
  

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-OutdoorEducati1.014