Youth Entrepreneurship Program Director, Founders School - $200,000/year USD

Traditional high schools evaluate students based on test scores and GPA. At Founders School, success is measured by businesses created, real problems solved, and students accomplishing what most adults would consider unattainable.

We're seeking an individual who can inspire, push, and guide ambitious teenage entrepreneurs as they launch actual companies, adopt AI, and tackle challenges most people defer until their twenties or beyond.

If high expectations, significant autonomy, and empowering exceptional youth to reach extraordinary milestones excites you, continue reading.

What You Will Be Doing

• Lead daily execution and forward momentum for your student cohort using standups, coaching conversations, and structured accountability systems.
• Facilitate weekly 1:1 coaching and daily check-ins to help students navigate roadblocks and sustain their progress.
• Track student activity in FounderOS, spot slowing momentum early, and mobilize support resources as necessary.
• Link students with mentors, founders, operators, and growth opportunities that speed their development.
• Organize workshops, events, and community activities that deepen culture and elevate performance standards.
• Demonstrate practical AI application and support students in integrating AI into their businesses, workflows, and decision-making.
• Accompany students on 3-4 school trips annually.

What You Won’t Be Doing

• Delivering in-depth strategic business advisory as students scale their ventures. That responsibility belongs to FounderOS, Entrepreneurs-in-Residence, and visiting mentors.
• Tolerating results that fall short of a student's proven capabilities.
• Instructing academic coursework. That experience is owned by the academic platform and faculty.
• Facilitating workshops beyond your domain of expertise.
• Making low-value introductions or sharing generic resources inconsistent with Founders School standards.

Youth Entrepreneurship Program Director Key Responsibilities

Build the culture, accountability frameworks, and support infrastructure that enable ambitious student founders to execute consistently, apply AI with confidence, and deliver outcomes that exceed what conventional education systems allow.

Basic Requirements

• 3+ years in leadership or high-impact individual contributor positions at startups, growth-stage companies, or similarly rigorous settings.
• The capacity to participate confidently in entrepreneurial discussions and recognize when specialized expertise should be engaged.
• A specific strength beyond coaching: workshop design, event execution, content development, community activation, relationship cultivation, or a similarly impactful skill.
• The capacity to earn the attention of ambitious teenagers and build an environment they are drawn to.
• The capacity to provide candid, challenging feedback that elevates motivation and results.
• Active daily use of AI tools with concrete examples 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.

Nice-to-have Requirements

• Started or co-founded a business.
• Background coaching, mentoring, or leading initiatives for teenagers or young adults.
• Established network of founders, operators, investors, or mentors.
• Early-stage startup background where you managed multiple roles and created systems from the ground up.

About Founders School

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-Elizabet-YouthEntrepren