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

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

The best way to support a student who's struggling is to hold the standard firm. If that resonates with you — and if you'd prefer to prove that principle outdoors with a group of students rather than lecture about it indoors — this role is worth your attention.

This is not traditional teaching. Waypoint Academy students don't sit in rows listening to lectures. They progress through adaptive learning software independently while you guide them on persistence, focus, and achieving their goals. You'll take them outside: facilitating one-hour life-skills sessions on leadership, teamwork, public speaking, and problem-solving through adventure-based, experiential challenges designed to be both demanding and engaging. Every session concludes with a Test2Pass mastery check — students must demonstrate the skill in a real scenario before completion.

The remainder of your time is spent conducting motivation sessions: brief, one-on-one coaching conversations informed by Coachbot analytics, where you engage students and propel them toward their academic objectives. You'll observe measurable, immediate transformation as students shift from reluctant participants to self-assured achievers. Your performance metrics are transparent: student satisfaction scores (90% goal) and weekly goal completion (100% goal).

High performers advance to senior coaching positions: leading a team and influencing how the school motivates and supports its students. Beyond that lies complete school ownership — accountability for outcomes, culture, everything. Dripping Springs sits 30 minutes from Austin's tech industry, live music venues, and culinary landscape, offering 300 days of sunshine and year-round Hill Country outdoor access.

If you've always known there's a more effective approach to reaching students, submit your application today.

What You Will Be Doing

• Facilitating 1-hour outdoor life-skills sessions (leadership, public speaking, teamwork, focus) through adventure-based, nature-oriented activities following Waypoint's curriculum and structured playbook
• Conducting individual motivation sessions with students, leveraging Coachbot analytics and student profile information to guide them toward weekly academic objectives
• Completing each session with a Test2Pass mastery check: students must demonstrate the targeted life skill in an authentic context before the workshop ends
• Exercising outdoor safety judgment prior to every session: evaluating routes and weather, conducting gear inspections, and adhering to Leave No Trace principles per Waypoint's field protocols
• Energizing sessions through storytelling, imaginative customization, and the presence required to engage a cohort of K-12 students both indoors and outdoors
  
  

What You Won’t Be Doing

• Teaching academic content or standing in front of a classroom. Students complete coursework via adaptive EdTech software; you coach them through obstacles rather than delivering lessons.
• Supervising students while they work on screens. You'll be actively leading outdoor sessions, conducting motivation coaching, and supporting students who need help.
• Evaluating assignments, creating lesson plans from the ground up, or preparing students for standardized assessments.
• Reducing expectations for a student facing challenges. Standards remain firm, mastery is required, and your responsibility is to coach students to success — not adjust the target.
• Handling parent outreach or administrative tasks. Those functions are managed by the Campus Lead.
  
  

Outdoor Education Coach Key Responsibilities

Support K-12 students at Waypoint Academy to love learning, accelerate their progress, and develop lasting life skills.

Basic 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 exceptional personal achievement: competitive sports, academic distinction, or high-level professional accomplishment
• Strong public speaking ability with the capacity to engage and maintain attention from large student groups in both indoor and outdoor settings
• Innate skill for building rapport with K-12 learners as a positive role model who challenges them to improve, rather than as a peer who accepts mediocrity
• Authorization to work in the United States without requiring visa sponsorship
• Available to work on-site at the Waypoint Academy campus in Dripping Springs, TX (near Austin)
  
  

Nice-to-have Requirements

• Background as an athletic coach, outdoor expedition leader, camp director, or wilderness education instructor
• Wilderness safety or first aid certification
• Experience with adaptive learning platforms like Khan Academy or IXL
• Foundation in experiential education, youth development, or outdoor youth programs
  
  

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-OutdoorEducati.013