Careers at Waypoint Academy
Guide students through adventure-based learning that shapes capable leaders.
The education Olympics
Salary without side gigs
Skills make the grade
JOIN WAYPOINT ACADEMY
What if school created leaders instead of test-takers?
Waypoint Academy is a nature-based school launching in Dripping Springs, where students complete focused academics in the morning and build grit, confidence, and leadership through outdoor challenges in the afternoon. Everything from survival skills, archery, rucking, and strength training is in the curriculum.
- Turn challenge into confidence: Help students do hard things, trust themselves, and lead with next-level courage.
- Make academics more purposeful: Support a school day where efficient learning creates room for real-world growth.
- Build beyond the classroom: Work with students through experiences that develop discipline, teamwork, and authentic independence.
If you want your work to help students become stronger thinkers, braver leaders, and more capable young people, Waypoint Academy is building school beyond four walls.
Shape students who can lead when the path gets hard.
Available Jobs
Find your place at Waypoint Academy...
3 Jobs in Other States
DRIPPING SPRINGS, TX
Lead Guide
DRIPPING SPRINGS, TX
Reading Specialist
DRIPPING SPRINGS, TX
Admissions Associate - Waypoint
See all Current Openings →.
Lead Guide @ Waypoint Academy
Dripping Springs, TX, US
In-person
8am to 5pm, Monday to Friday
full-time (40 hrs/week)
Long-term role
Key responsibilities
Make sure every student in your cohort loves school, grows academically, and builds the character and life skills to thrive.
Description
- On-site at Waypoint Academy in Dripping Springs, Texas
- $150,000/year as a W2 employee, paid weekly. Day-one health benefits.
- Relocation support available
The most supportive thing you can do for a kid is hand them something hard and refuse to carry it for them. If that makes you uneasy, stop reading. If it makes you nod, keep going.
At Waypoint Academy, core academics run on self-guided, AI-powered adaptive apps that compress the school day into a focused morning. No lectures. That frees you for the work that actually changes a kid's trajectory. Your morning might open with a one-on-one coaching session with a Guide, reviewing student data to find where a cohort is slipping. By midday you're outdoors, leading a workshop that teaches teamwork and resilience through a real challenge. Afternoons shift to motivation sessions: sitting with individual students, learning what drives them, and getting a resistant kid moving toward their goals. You carry your own cohort the whole time, so you stay sharp on the skills you coach in others.
You've probably been the square peg in education: too data-driven, too results-focused, too willing to take kids outside and let them struggle. This might be the first place that fits. You coach other Guides from day one, and as you deliver results, the standard you set ripples across the whole cohort and your influence over the program grows. You'll see the payoff in person: a skeptical kid who starts owning their progress, a Guide who gets sharper because you told them the truth, a student who walks out of the woods more capable than they walked in.
Hold the standard. Take them outside. Apply now.
Candidate requirements
- Willing to work in person at Waypoint Academy in Dripping Springs, Texas
- Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or a related field
- At least 5 years in education, youth development, coaching, outdoor education, or learning and development (L&D)
- Track record of leading a team of 5 or more adults, including hiring and performance-based termination decisions
- Direct experience working with youth ages 5-18 in an educational or developmental setting
- Built, launched, or significantly grew a program, team, school, or outdoor initiative from the ground up, with a specific and measurable example
- Proven use of data and metrics to set goals and drive decisions, not just report results
- Legally authorized to work in the United States
Inside the EdTech team experience
Watch Interview
Holly | LL Guide and Reading Specialist
United States
Holly spent years helping students build skills that don’t always show up on a report card - confidence, planning, independence, and the belief that they can do hard things. But in public school, that kind of whole-child support was limited by paperwork & syst...
Meet Holly
School Meets Adventure
Most schools separate learning from real life. Waypoint Academy brings them together.
Students spend their mornings mastering core subjects through adaptive learning technology and their afternoons tackling hands-on challenges that build resilience, teamwork, leadership, and confidence. Learning happens both in the classroom and in the wild.
At Waypoint, education is measured not just by knowledge gained, but by character developed.
Learning at the Speed of Potential
Waypoint Academy believes every learner progresses differently. Instead of age-based pacing, students advance through mastery, responsibility, and demonstrated competence.
AI-powered learning tools personalize academic instruction, enabling students to progress faster while gaining deeper ownership of their educational journey. Guides act as mentors and coaches, helping learners think critically rather than simply providing answers.
The goal isn't compliance—it’s creating capable, independent thinkers who can direct their own future.
Building Humans, Not Just Students
Waypoint Academy was created around a simple belief: children are capable of far more than traditional education often expects.
Through outdoor challenges, meaningful projects, peer accountability, and real-world experiences, learners develop the habits and mindset required to navigate uncertainty, solve problems, and lead with confidence.
The ultimate outcome isn't better students—it’s stronger, more resilient humans.
2×
Faster learning with AI
2Hr
Core academics in just 2 hours daily
300+
Part of the Acton Academy network
20+
Countries with learners
Waypoint Academy's exclusive hiring partner
Waypoint Academy partners with Crossover to recruit high-performing people who can help bring their 2 hour learning model to life. Crossover’s hiring process looks beyond resumes, using structured screening, cognitive assessments, practical work samples, and interviews to identify candidates with the talent and judgment to make a real impact in education.
For applicants, that means a clearer path to show what you can do. For Waypoint Academy, that means finding people ready to do the innovative work modern education demands.
Lead the future of learning when you’re hired on Crossover.
How it works
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.
STEP 1
Chat-style screening interview.
STEP 2
Cognitive aptitude test.
STEP 3
Prove real-world job skills.
STEP 4
Interview with the hiring manager.
STEP 5
Pass proctored test.
STEP 6
Accept job offer.
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FAQs
Frequently asked questions about Waypoint Academy
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