Student Success Coach $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
Description
- Dripping Springs, TX (near Austin): full-time, on-site position
- $100,000 annual salary, paid weekly; health, dental, and vision coverage from day one
- Relocation assistance provided
The most powerful support you can offer a struggling student is holding the standard high. If that resonates with you — and if you'd prefer to take a group into the field to demonstrate it rather than lecture about it indoors — read on.
This role is not traditional teaching. At Waypoint Academy, students don't absorb content in lecture halls. Instead, they progress through adaptive learning technology at their own speed while you guide them on persistence, focus, and achieving their goals. You'll bring them outside for one-hour experiential life-skills workshops covering public speaking, teamwork, leadership, and problem-solving through adventure-based activities designed to be challenging and engaging. Every session concludes with a Test2Pass mastery check — students must demonstrate the target skill in a real scenario before completion.
The remainder of your time is dedicated to motivation sessions: brief, one-on-one coaching conversations informed by Coachbot analytics, where you engage students and drive progress toward their academic objectives. You'll witness measurable, immediate transformation as students shift from reluctant participants to confident achievers. Your performance metrics are visible: student satisfaction ratings (90% target) and weekly goal completion (100% target).
High performers advance to senior coaching positions: overseeing a team and influencing the school's approach to student motivation and development. Beyond that lies complete school ownership — accountability for outcomes, culture, and operations. Dripping Springs sits 30 minutes from Austin's technology hub, live music venues, and culinary scene, offering 300+ days of sunshine and year-round Hill Country outdoor access.
If you've always known there's a more effective way to connect with students, submit your application now.
What you will be doing
- Facilitating 1-hour outdoor life-skills workshops (leadership, public speaking, teamwork, focus) through adventure-based, nature-centered activities following Waypoint's curriculum and playbook
- Conducting motivation sessions with individual students, leveraging Coachbot analytics and student profile information to guide them toward weekly academic targets
- Concluding every workshop with a Test2Pass mastery check: students must demonstrate the target life skill in authentic context before the session is complete
- Exercising outdoor safety judgment prior to each session: evaluating routes and weather, conducting gear inspections, and following Leave No Trace principles per Waypoint's field protocols
- Energizing sessions through storytelling, creative adaptation, and the presence to maintain engagement from K-12 learners both indoors and outdoors
What you will NOT be doing
- Teaching academic content or standing at a whiteboard. Students engage with course material via adaptive EdTech software; you coach them through obstacles, not teach curriculum.
- Supervising students on devices. You'll be actively leading outdoor workshops, conducting motivation sessions, and coaching students who are stuck.
- Grading assignments, creating lesson plans from the ground up, or preparing students for standardized exams.
- Adjusting expectations downward for struggling students. Goals remain firm, mastery is non-negotiable, and your role is to coach students to success — not lower the standard.
- Handling parent communications or administrative tasks. Those duties fall to the Campus Lead.
Key responsibilities
Support K-12 students at Waypoint Academy to love learning, accelerate their progress, and develop enduring life skills.
Candidate 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
- Demonstrated history of exceptional personal achievement: competitive sports, academic distinction, or elite professional accomplishment
- 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 improve, not as a friend who accepts minimal effort
- 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
- Experience as a sports 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
- Background in experiential education, youth development, or outdoor youth programs
Meet the hiring manager
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
Frequently asked questions
Reviews
Meet some people who've landed similar jobs
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
Join the world's largest community of 
AI-first remote workers.