Camp Director, Waypoint Academy - $150,000/year USD

About the role

The most meaningful gift you can give a young person is a difficult challenge paired with the expectation they will rise to meet it. If that principle unsettles you, this role isn't for you. If it resonates, read on.

What You Will Be Doing

• Develop the Guides on your team: analyze performance metrics, observe their student interactions, and conclude each session with concrete next steps that address performance gaps.
• Facilitate one-hour outdoor skill-building sessions where students in grades K-12 develop leadership, grit, collaboration, and communication through experiential challenge activities.
• Conduct motivation meetings informed by student analytics and Coachbot insights to ensure each student advances toward objectives and takes responsibility for their trajectory.
• Maintain your own cohort of students while coaching other Guides, grounding your leadership in active practice rather than distant recollection.
• Monitor student engagement, goal attainment, and Guide effectiveness on a weekly basis to identify and address underperformance early.

What You Won’t Be Doing

• Delivering lectures or providing academic tutoring.
• Designing original curriculum or creating lesson plans.
• Training Guides in instructional methods.
• Compromising standards to avoid conflict.
• Advancing underperforming students or overlooking Guide deficiencies.
• Confining students to indoor classroom environments.

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 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
• Licence to work in the United States

Nice-to-have Requirements

• 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

About Waypoint Academy

Nature-based school that blends rigorous academics with real-world challenges.

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 $75 USD/hour, which equates to $150,000 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.