Student Success Coach, Waypoint Academy – $100,000/year USD

• Dripping Springs, TX (near Austin): full-time, on-site position
• $100,000 annually, paid every week; 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 high. If that principle resonates with you — and if you’d rather lead a group into the field to demonstrate it than discuss it in a classroom — this role is worth your attention.

This is not traditional teaching. Students at Waypoint Academy don’t sit in rows listening to lectures. They progress through adaptive learning software independently while you coach them on persistence, focus, and achieving their goals. You’ll bring them outdoors for one-hour life-skills workshops covering leadership, public speaking, teamwork, and problem-solving through adventure-based, experiential activities designed to be challenging and engaging. Every session ends with a Test2Pass mastery check — students must demonstrate the target skill in a real setting before completion.

The remainder of your time is spent conducting motivation sessions: brief, one-on-one coaching conversations informed by Coachbot analytics, helping students stay on track toward their academic objectives. You’ll see students shift from disengaged learners to self-assured achievers — visibly and quickly. Your performance is transparent: student satisfaction scores (90% goal) and weekly target completion (100% goal).

High performers advance to senior coaching positions: leading a team and influencing how the school motivates and supports students. Beyond that lies full school ownership — accountability for outcomes, culture, and operations. Dripping Springs is a 30-minute drive from Austin’s tech sector, live music venues, and culinary scene, with over 300 sunny days annually and year-round Hill Country outdoor recreation.

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

What you will be doing

• Facilitating 1-hour outdoor life-skills workshops (leadership, public speaking, teamwork, focus) using nature-based, adventure-style activities according to Waypoint’s curriculum and playbook
• Conducting motivation sessions with students individually, leveraging Coachbot analytics and student profile information to guide them toward weekly academic goals
• Concluding every workshop with a Test2Pass mastery check: students must demonstrate the life skill being taught in a real-world context before the session is complete
• Exercising outdoor safety judgment prior to each session: evaluating routes and weather, inspecting gear, and following Leave No Trace principles according to Waypoint’s field guidelines
• Energizing sessions through storytelling, creative adaptation, and the presence needed to engage a cohort of K-12 students both indoors and outdoors

What you will NOT be doing

• Teaching academic lessons or standing at a whiteboard. Students access course material via adaptive EdTech software; you coach them through obstacles, not teach content.
• Supervising students at computers. You’ll be actively leading outdoor workshops, conducting motivation sessions, and supporting students who are stuck.
• Grading assignments, creating lesson plans from the ground up, or preparing students for standardized exams.
• Reducing expectations for a struggling student. Goals remain real, mastery is the benchmark, and your responsibility is to coach students to meet it — not adjust it.
• Handling parent correspondence or administrative duties. These tasks fall to the Campus Lead.

Key Responsibilities

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

Candidate Requirements

• Bachelor’s degree in any field
• Minimum of 3 years working directly with K-12 students in educational, camp, coaching, or outdoor education environments
• Documented history of high personal achievement: elite athletic performance, academic distinctions, or exceptional professional accomplishments
• Strong public speaker capable of engaging and maintaining attention from large student groups, both indoors and outdoors
• Genuine ability to relate to K-12 learners as a positive role model who challenges them to improve, rather than a peer who accepts excuses
• Legal authorization to work in the U.S. without requiring visa sponsorship
• Available to work on-site at the Waypoint Academy campus in Dripping Springs, TX (near Austin)

Nice to have

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

This position is also known as:

• K-12 Learning Coach
• Outdoor Education Coach
• Outdoor Education Teacher
• Adventure Learning Instructor
• Experiential Education Facilitator
• Youth Leadership Coach