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

• On-campus position in Dripping Springs (Austin area), TX
• $100,000 annual salary, distributed weekly. Health, dental, and vision coverage starts day one
• Relocating? Assistance provided
  
  

Waypoint Academy is redefining education by replacing traditional classroom instruction with adventure-based skill development and AI-powered personalized academics. Students don't remain seated while listening to lectures—they develop public speaking abilities on outdoor trails, cultivate leadership through collaborative challenges, and progress at twice the typical pace using tailored software.

This role is about coaching K-12 students to unlock their capabilities through outdoor experiences and motivational goal-setting sessions, not traditional teaching. You'll facilitate nature-based activities that develop tangible competencies (concentration, communication, collaboration), rather than delivering standard curriculum. High achievers who envision a radically reimagined school model excel in this environment. You'll witness students evolve from hesitant learners into self-assured performers—measurably and in real time.

Dripping Springs delivers Hill Country scenery just 30 minutes from Austin's technology hub, live music, and culinary offerings. Over 300 sunny days annually, Barton Springs access, and year-round outdoor opportunities.

Guide their development. Direct the adventure. Submit your application today.

What You Will Be Doing

• Facilitating 1-hour outdoor life-skills sessions (public speaking, concentration, leadership, collaboration) using nature-based challenges and adventure-style programming
• Conducting brief, high-energy motivational sessions where you guide students toward academic targets using adaptive software
• Animating curriculum through storytelling, personalization, and dynamic delivery that sustains K-12 student engagement at high levels
• Implementing safety procedures and outdoor decision-making (route selection, weather assessment, equipment inspection, Leave No Trace fundamentals) according to Waypoint's field standards
• Evaluating skill acquisition through demonstrations where students show they can execute the life skill in practical scenarios
• Maintaining rigorous standards of excellence while serving as an approachable, motivating role model students genuinely admire
  
  

Basic Requirements

Student Success Coach key responsibilities

• Bachelor's degree in any discipline
• At least 3 years of experience engaging with K-12 students in educational, camp, coaching, or outdoor program settings
• Documented history of high achievement (academic, athletic, or professional)
• Strong public speaker capable of energizing and maintaining attention from large student groups, both indoors and outdoors
• Innate capacity to connect with K-12 learners, their interests, and their culture—not as a peer but as a positive role model who challenges them to develop
• Authorization to work legally in the United States without requiring visa sponsorship
• Commitment to on-site work at Waypoint Academy's campus in Dripping Springs, TX (near Austin)
  
  

Nice-to-have Requirements

• First aid or wilderness safety training
  
  

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-Austin-StudentSuccess