In-Person Instructional Coach: Outdoor Leadership & Student

Position: In-Person Instructional Coach: Outdoor Leadership & Student Growth

• In-person role at Waypoint Academy, Dripping Springs, Texas
• Annual salary of $150,000 as W2, weekly pay schedule. Full health benefits from day one.
• Relocation assistance provided

• In-person role at Waypoint Academy, Dripping Springs, Texas
• Annual salary of $150,000 as W2, weekly pay schedule. Full health benefits from day one.
• Relocation assistance provided

The kindest thing you can offer a child is a real challenge—and the refusal to solve it for them. If that idea unsettles you, this isn't your role. If it resonates, read on.

Waypoint Academy runs core academics through self-directed, AI-adaptive software that condenses instruction into a focused morning session. No traditional lectures. That structure frees you to do the work that genuinely shifts outcomes. Your morning may begin with a coaching conversation alongside a Guide, analyzing student data to pinpoint where a group is falling behind. By midday, you're outside facilitating a workshop that builds teamwork and grit through hands-on problem-solving.

Afternoons are reserved for motivational work: sitting down with individual students, uncovering what drives them, and moving a reluctant learner toward meaningful goals. You maintain your own cohort throughout, keeping your coaching grounded in live experience.

You've likely felt out of place in traditional education: too metric-focused, too outcome-oriented, too comfortable putting kids in challenging situations and watching them work through it. This may be the first environment where that approach is valued. You'll coach other Guides from the outset, and as your results accumulate, the standard you model spreads across cohorts and your influence over the program deepens.

The impact is tangible: a doubtful student who begins to take ownership, a Guide who sharpens because you gave honest feedback, a young person who emerges from an outdoor challenge more self-assured.

Uphold the standard. Get them outside. Apply today.

What You Will Be Doing

• Provide coaching to fellow Guides: analyze performance metrics, observe their interactions with students, and conclude each session with clear, actionable next steps.
• Facilitate one-hour outdoor workshops for K-12 students focused on developing leadership, resilience, collaboration, and communication via adventure-based activities.
• Conduct individual motivation sessions informed by student analytics and Coachbot insights to drive every student toward goal ownership and forward progress.
• Maintain your own student cohort concurrently with developing other Guides, ensuring your coaching stems from active practice rather than past experience.
• Monitor student satisfaction, goal attainment, and Guide performance on a weekly basis to identify and address underperformance early.

What You Won’t Be Doing

• Delivering lectures or academic tutoring. Students engage with content via self-paced adaptive platforms, frequently without direct adult supervision.
• Creating original curriculum or lesson frameworks. Structured playbooks are already in place; your role is execution with high fidelity and energy.
• Training Guides on instructional delivery. Because Guides don't lecture, your coaching centers on motivation, accountability, and presence with students.
• Compromising standards to avoid conflict. You will not advance a student prematurely or overlook underperformance in a Guide.
• Confining students to indoor, seated environments. A significant portion of learning occurs outdoors through experiential challenge.

Instructional Coach

Key Responsibilities

Ensure every student in your cohort enjoys school, progresses academically, and develops the character and life skills necessary to succeed.

Basic 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…