Youth Entrepreneurship Program Director, Founders School

Traditional high schools define success using grades and standardized tests. At Founders School, success is defined by the businesses students create, the real-world problems they solve, and their ability to accomplish what most adults would deem unattainable.

We need someone capable of inspiring, pushing, and guiding ambitious teenage entrepreneurs as they launch genuine companies, harness AI capabilities, and tackle challenges typically reserved for adulthood.

If high expectations, significant autonomy, and empowering exceptional young people to reach remarkable outcomes excites you, continue reading.

• Propel daily progress and energy across your assigned student cohort using standups, coaching conversations, and accountability frameworks.
• Lead weekly one-on-one coaching meetings and daily touchpoints that enable students to navigate challenges and sustain forward motion.
• Track student activity within FounderOS, spot signs of stagnation quickly, and mobilize support resources as required.
• Facilitate introductions to mentors, founders, operators, and growth opportunities that speed up student development.
• Organize workshops, gatherings, and community-building activities that deepen culture and elevate performance expectations.
• Demonstrate hands-on AI application and guide students in integrating AI into their ventures, operations, and strategic thinking.
• Accompany students on 3-4 school trips annually.

• Offering in-depth strategic business advisory as students develop their companies. That responsibility belongs to FounderOS, Entrepreneurs-in-Residence, and external mentors.
• Tolerating output that doesn't align with a student's proven capabilities.
• Delivering academic instruction. The academic platform and teaching staff manage that function.
• Facilitating workshops beyond your core competencies.
• Providing generic tools or connections that fail to reflect Founders School quality standards.

Build the culture, accountability structures, and support mechanisms that allow driven student founders to execute reliably, apply AI with skill, and produce results that exceed the boundaries of conventional education.

• 3+ years in leadership positions or high-impact contributor roles at startups, scaling companies, or similarly rigorous settings.
• Confidence participating in entrepreneurial discussions and discernment about when specialized expertise is needed.
• A standout capability beyond coaching: workshop design, event coordination, content development, community cultivation, network expansion, or another equally impactful skill.
• The capacity to capture the focus of ambitious teenagers and build an environment they're eager to join.
• The skill to present challenging feedback that strengthens both motivation and results.
• Regular use of AI tools with concrete demonstrations of how AI enhances your output.
• Availability to work on-site in New York City (relocation assistance available).
• Legal authorization to work in the United States.

• Founded or co-founded a company.
• Background coaching, mentoring, or directing programs for teenagers or young adults.
• Established network of founders, operators, investors, or mentors.
• Early-stage startup background where you managed diverse 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.

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.