Lead Guide $150,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Description
- 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.
What you will be doing
- Coach the Guides who work alongside you: review performance data, observe them with students, and end every session with specific actions that close the gap.
- Lead one-hour outdoor life-skill workshops where K-12 students build leadership, resilience, teamwork, and communication through adventure-based challenges.
- Run motivation sessions using student analytics and Coachbot data to get every student moving toward their goals and owning their own progress.
- Carry your own student cohort while developing other Guides, so you coach from current experience, not memory.
- Track student satisfaction, goal completion, and Guide performance weekly to catch underperformance before it compounds.
What you will NOT be doing
- Lecturing or tutoring students on academic subjects. They learn through self-guided adaptive apps, often with no adult in the room.
- Building curriculum or lesson plans from scratch. The playbooks exist; the bar is fidelity and energy, not originality.
- Coaching Guides on teaching technique. Guides don't lecture, so you coach motivation, accountability, and how they show up with kids.
- Lowering the bar to keep the peace. You won't pass a student along or smooth over a Guide's underperformance.
- Keeping kids inside and in their seats. Much of the learning here happens outdoors, through challenge.
Key responsibilities
Make sure every student in your cohort loves school, grows academically, and builds the character and life skills to thrive.
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
Nice to have
- Master's degree in a related field
- Coached athletics, led wilderness or experiential programs, directed camps, or ran youth programs at a scale that required running cohorts and measuring outcomes
- Left classroom teaching to build or run programs from a different seat: EdTech, tutoring, youth nonprofits, or school intervention teams
- Early-career track record of high personal performance, academic, athletic, or professional, before moving into leadership
- Belief that the standard education model is broken and personal investment in rebuilding it
You will be working for
Meet a successful candidate
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.
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