What are the responsibilities and job description for the Youth Entrepreneurship Program Director, Founders School - $200,000/year USD position at Crossover?
Traditional high schools define achievement by test scores and GPAs. At Founders School, achievement means launching businesses, solving meaningful problems, and helping students accomplish what most adults would think impossible.
We need someone who can inspire, push, and guide ambitious teenage entrepreneurs as they create real ventures, harness AI, and work toward objectives most people delay until well into adulthood.
If high standards, strong ownership, and supporting exceptional young people to reach extraordinary results excites you, continue reading.
What You Will Be Doing
Build the culture, accountability frameworks, and support infrastructure that empower ambitious student founders to execute consistently, apply AI with skill, and produce results that surpass what conventional schooling allows.
Basic Requirements
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. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
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 $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 www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5816-US-NewYork-YouthEntrepren
We need someone who can inspire, push, and guide ambitious teenage entrepreneurs as they create real ventures, harness AI, and work toward objectives most people delay until well into adulthood.
If high standards, strong ownership, and supporting exceptional young people to reach extraordinary results excites you, continue reading.
What You Will Be Doing
- Maintain daily momentum and execution across your student cohort using standups, coaching conversations, and accountability frameworks.
- Lead weekly one-on-one coaching and daily touchpoints that support students in clearing roadblocks and sustaining forward progress.
- Track student activity in FounderOS, spot stalled momentum quickly, and mobilize support resources as necessary.
- Introduce students to mentors, entrepreneurs, operators, and growth opportunities that speed their development.
- Facilitate workshops, events, and community programming that deepen culture and elevate performance expectations.
- Demonstrate real-world AI application and guide students in integrating AI into their ventures, systems, and thinking.
- Accompany students on 3-4 school trips annually.
- Delivering in-depth strategic business advisory as students develop their ventures. FounderOS, Entrepreneurs-in-Residence, and external mentors handle that function.
- Tolerating output that doesn't match a student's proven capability.
- Teaching traditional academic coursework. The academic platform and instructional team manage that domain.
- Leading workshops that fall outside your skillset.
- Offering generic connections or materials that fail to meet Founders School quality standards.
Build the culture, accountability frameworks, and support infrastructure that empower ambitious student founders to execute consistently, apply AI with skill, and produce results that surpass what conventional schooling allows.
Basic Requirements
- 3 years in leadership positions or high-impact individual contributor roles at startups, growth-stage organizations, or similarly rigorous settings.
- Comfort participating in entrepreneurial discussions and awareness of when to involve specialized expertise.
- A unique strength beyond coaching: workshop design, event orchestration, content production, community cultivation, relationship building, or another equally impactful skill.
- The capacity to capture the attention of driven teenagers and build an environment they're eager to join.
- The skill to provide challenging feedback that strengthens both motivation and output.
- Regular use of AI tools with concrete demonstrations of how AI enhances your productivity.
- Availability to work on-site in New York City (relocation assistance available).
- Legal authorization to work in the United States.
- Experience founding or co-founding a company.
- Background coaching, mentoring, or managing programs for teenagers or young adults.
- A personal network of founders, operators, investors, or mentors.
- Early-stage startup experience in multi-functional roles where you 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. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
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 $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 www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5816-US-NewYork-YouthEntrepren
Salary : $200,000