Entrepreneurship Coach, Founders School

Traditional high schools evaluate achievement by grades and standardized tests. Founders School evaluates achievement by businesses built, real problems tackled, and student accomplishments most adults would think impossible.

We need someone capable of inspiring, pushing, and coaching driven teenage entrepreneurs as they launch genuine companies, harness AI capabilities, and chase ambitions typically reserved for adulthood.

If high expectations, complete ownership, and guiding talented young people to exceptional results excites you, continue reading.

• Push daily execution and forward momentum across your student cohort via standups, coaching conversations, and accountability frameworks.
• Lead weekly one-on-one coaching meetings and daily touchpoints that support students in clearing roadblocks and sustaining progress.
• Track student activity in FounderOS, catch stalled momentum early, and arrange support resources as necessary.
• Link students to mentors, founders, operators, and growth opportunities that speed their development.
• Deliver workshops, events, and community programming that deepen culture and elevate performance expectations.
• Demonstrate hands-on AI application and guide students in embedding AI into their ventures, operations, and strategic thinking.
• Travel alongside students for 3-4 school trips annually.

• Delivering in-depth strategic business guidance as students develop their ventures. FounderOS, Entrepreneurs-in-Residence, and guest mentors handle that function.
• Tolerating output below a student's proven capability.
• Instructing traditional academic coursework. The academic platform and faculty manage that domain.
• Leading workshops beyond your specialized knowledge.
• Offering generic materials or connections that fail to meet Founders School quality standards.

Build the culture, accountability structures, and support infrastructure that empower ambitious student founders to execute reliably, apply AI strategically, and produce results that surpass the limits of conventional education.

• 3+ years in leadership positions or high-impact individual contributor capacities at startups, scaling companies, or equivalently rigorous settings.
• Comfort participating in entrepreneurial discussions and discernment to escalate for specialized insight.
• A unique capability beyond coaching: workshop design, event orchestration, content production, community cultivation, network development, or comparable value.
• Capacity to earn the respect of motivated teenagers and foster an environment they are drawn to.
• Skill in delivering challenging feedback that strengthens motivation and output.
• Routine application of AI tools with concrete proof of how AI elevates your productivity.
• Readiness to work on-site in New York City (relocation assistance available).
• Legal authorization to work in the United States.

• Launched or co-launched a company.
• Background coaching, mentoring, or directing programs for teenagers or emerging adults.
• Established connections among founders, operators, investors, or mentors.
• Startup experience in early phases where you balanced multiple responsibilities and created systems from the ground up.

Founders School is a four-year high school built for ambitious students who want to create, build, and solve meaningful problems. The program combines Alpha School's elite academics, real-world experience, and mentorship from world-class entrepreneurs around three commitments to every student:
Build a million-dollar business. Identify problems in the world worth solving. Master AI before adults do.

This is a place for people who'd rather build the thing than manage the thing. We're hiring the founding team that builds the dream high school for the most entrepreneurial and ambitious students in the country. Launching in NYC Fall 2026.

There is so much to cover for this exciting role, and space here is limited. We look forward to meeting you!

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 $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult  for more details on this topic.

Crossover Job Code: LJ-5816-US-New Jerse-Entrepreneur sh.
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