Entrepreneurship Program Manager, Founders School

Traditional high schools define success by grades and standardized test results. At Founders School, success is defined by businesses students launch, real problems they solve, and outcomes most adults would consider unattainable.

We need someone capable of motivating, challenging, and developing driven teenage entrepreneurs as they launch actual companies, master artificial intelligence, and pursue ambitions most people delay until adulthood.

If high standards, complete ownership, and guiding exceptional young people toward extraordinary results energize you, continue reading.

• Maintain daily execution and forward momentum across your assigned student cohort via standups, coaching, and accountability mechanisms.
• Lead weekly one-on-one coaching conversations and daily touchpoints that enable students to navigate challenges and sustain progress.
• Track student activity in FounderOS, spot stagnation before it compounds, and mobilize support infrastructure as situations require.
• Facilitate connections between students and mentors, founders, operators, and growth opportunities.
• Design and execute workshops, events, and community initiatives that reinforce culture and elevate performance expectations.
• Demonstrate applied AI usage and guide students in integrating AI into their ventures, operations, and strategic thinking.
• Accompany students on 3-4 annual school trips.

• Delivering in-depth strategic business consulting while students operate their ventures. That function belongs to FounderOS, Entrepreneurs-in-Residence, and external mentors.
• Tolerating output that sits below a student's proven capability.
• Instructing traditional academic content. The academic platform and teaching staff manage that domain.
• Facilitating workshops in areas where you lack mastery.
• Offering generic connections or materials that fail to meet Founders School quality benchmarks.

Build the culture, accountability structures, and support infrastructure that empower ambitious student entrepreneurs to execute reliably, apply AI strategically, and deliver results that exceed what conventional education systems allow.

• 3+ years in leadership or high-impact individual contributor positions at startups, scaling companies, or equivalently rigorous settings.
• Comfort engaging in entrepreneurial dialogue and discernment to escalate when specialized expertise is required.
• A unique capability beyond coaching: workshop design, event orchestration, content development, community cultivation, relationship architecture, or comparable value-add.
• Capacity to capture and hold the focus of ambitious teenagers and build an environment they actively choose.
• Skill in delivering challenging feedback that elevates both drive and results.
• Active daily use of AI tools, supported by concrete examples demonstrating productivity gains.
• Readiness to work on-site in New York City (relocation assistance available).
• U.S. work authorization.

• Entrepreneurial experience as a founder or co-founder.
• Track record coaching, mentoring, or directing programs for teenagers or emerging adults.
• Established network spanning founders, operators, investors, or mentors.
• Background in early-stage ventures where you managed diverse responsibilities and created operational systems.

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.

There is more to learn about this exciting role. 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
1.002