Outdoor Education 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 

Not accepting applications on crossover.com at this time.

Description

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

The highest form of support for a struggling student is holding the standard firm. If that principle resonates with you — and if you'd rather demonstrate it in the field with a group of students than discuss it in a classroom — this role is worth your attention.

This is not conventional teaching. Students at Waypoint Academy don't attend lectures in traditional rows. Instead, they progress through adaptive learning technology at their own speed while you coach them on persistence, concentration, and achieving their objectives. You will guide them outdoors: delivering one-hour life-skills sessions on leadership, teamwork, public speaking, and problem-solving through adventure-based experiential methods designed to challenge and engage. Every session concludes with a Test2Pass mastery assessment — students must demonstrate the skill in a real-world context before completion.

Your remaining time centers on motivation sessions: brief, individualized coaching dialogues informed by Coachbot analytics, where you engage with students and propel them toward their academic targets. You will witness students evolve from hesitant learners into self-assured performers — visibly and quickly. Your performance metrics are transparent: a 90% student satisfaction goal and a 100% weekly goal completion target.

High achievers advance to senior coaching positions: overseeing 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 culinary offerings, with over 300 sunny days and year-round access to Hill Country trails and recreation.

If you have always believed there is a more effective way to engage young learners, submit your application now.

What you will be doing

  • Facilitating 1-hour outdoor life-skills sessions (leadership, public speaking, teamwork, focus) using nature-based adventure activities from Waypoint's structured curriculum and playbook
  • Conducting individualized motivation sessions with students, leveraging Coachbot analytics and profile data to guide them toward weekly academic objectives
  • Completing each session with a Test2Pass mastery assessment: students must demonstrate the life skill in authentic context before the workshop concludes
  • Exercising outdoor safety protocols before every activity: evaluating routes and weather conditions, inspecting gear, and following Leave No Trace principles per Waypoint field standards
  • Energizing sessions through storytelling, creative adaptation, and the presence needed to engage K-12 learners both indoors and outdoors

What you will NOT be doing

  • Teaching academic content through lectures or whiteboard instruction. Students complete coursework via adaptive EdTech platforms; you coach them through obstacles, not content delivery.
  • Supervising students while they work on computers. Your time is spent leading outdoor sessions, facilitating motivation conversations, and supporting students who need assistance.
  • Evaluating assignments, creating lesson plans from the ground up, or preparing students for standardized assessments.
  • Reducing expectations for students facing difficulty. Standards remain fixed, mastery is non-negotiable, and your role is to coach students to meet the goal — not adjust it.
  • Handling parent outreach or administrative duties. These tasks fall under the Campus Lead's scope.

Key responsibilities

Support K-12 students at Waypoint Academy in developing a passion for learning, accelerating their progress, and acquiring durable life skills.

Candidate requirements

  • Bachelor's degree in any discipline
  • A minimum of 3 years working directly 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 skills with the ability to captivate and maintain engagement from large student groups in both indoor and outdoor settings
  • Innate capacity to relate to K-12 learners as an inspiring role model who challenges them to improve, rather than a peer who tolerates underperformance
  • Authorization to work in the United States without requiring visa sponsorship
  • Availability to work on-site at the Waypoint Academy campus located in Dripping Springs, TX (near Austin)

Nice to have

  • Experience in roles such as athletic coach, outdoor expedition leader, camp director, or wilderness education instructor
  • Certification in first aid or wilderness safety protocols
  • Knowledge of adaptive learning systems like Khan Academy or IXL
  • Professional background in youth development, experiential learning, or outdoor youth education programs

Meet the hiring manager

Watch Video
Watch Video

Meet a successful candidate

Watch Interview
Chris Hayes
Chris  |  L2 Guide
United States

Ever wondered if work is enhancing your life, or erasing it? After years of late nights as a fitness coach left him exhausted and disconnect...

Meet Chris

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.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

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

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

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.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.