Entrepreneurship Program Director, Founders School - $250,000/year USD at Crossover

Your job is to develop founders, not deliver curriculum.

Most schools prepare students for a future that remains hypothetical. We believe the future begins immediately. Founders School operates as a four-year high school designed for students unwilling to postpone their ambitions until adulthood. These students do not engage in simulated business exercises. They establish genuine companies, collaborate with experienced founders, develop mastery in AI, and address real-world challenges. Our expectations are elevated because our students possess elevated capabilities: launch a business generating one million dollars in revenue, uncover problems deserving attention, and achieve AI proficiency ahead of most adults. Your responsibility is to ensure that ambition translates into sustained execution.

You will not deliver traditional instruction or dictate operational strategy to students. Instead, you will coach a cohort of young entrepreneurs daily, ensuring they maintain accountability, navigate obstacles, and sustain momentum when entrepreneurship becomes challenging. You will recognize the right moments to push them harder, offer encouragement, or facilitate introductions to mentors and resources. The curriculum, Entrepreneurs-in-Residence, and founder network supply the technical and strategic guidance. You supply the structure, expectations, and drive that convert capability into measurable outcomes.

This role also represents a chance to construct something foundational. As part of our founding team in New York City, you will influence the culture, operational systems, and student experience at a school reimagining what secondary education can achieve. Your contributions will extend beyond a single cohort. They will inform the framework for every subsequent Founders School campus. If you are motivated by the startup ecosystem, believe rigorous standards unlock exceptional performance, and wish to dedicate your efforts to cultivating the next generation of entrepreneurs, we invite your application.

What You Will Be Doing

• Provide coaching and accountability to a cohort of student entrepreneurs through weekly one-on-one sessions, daily progress reviews, and group check-ins that ensure consistent, measurable advancement.
• Maintain exceptionally high standards for execution while delivering the guidance and accountability required to help students navigate challenges and continue building.
• Track student progress within FounderOS, recognize when momentum stalls, and facilitate connections to mentors, Entrepreneurs-in-Residence, or additional resources that drive accelerated development.
• Contribute to the creation of culture, recurring traditions, workshops, events, and the operational cadence of a world-class entrepreneurial high school.
• Accompany students on travel experiences several times annually while cultivating enduring relationships with founders, investors, operators, and entrepreneurial families.

What You Won’t Be Doing

• Serving as the primary business strategist or consultant for student ventures. That expertise comes from FounderOS, Entrepreneurs-in-Residence, and external mentors.
• Delivering conventional academic instruction or assessing traditional coursework.
• Tolerating mediocre effort from students with the capacity for outstanding achievement.
• Leading workshops on topics outside your domain of expertise or defaulting to generic entrepreneurial guidance.
• Operating within an inflexible institutional framework where administrative processes obstruct meaningful student progress.

Entrepreneurship Program Director Key Responsibilities

Establish an environment in which every student advances consistently as an entrepreneur by integrating outstanding coaching, rigorous accountability, strategic mentorship connections, and a culture that transforms ambitious teenagers into competent founders.

Basic Requirements

• A minimum of 3 years in a leadership or high-impact role within a startup or high-growth business.
• Sound business judgment and the confidence to engage meaningfully with early-stage founders while recognizing when to escalate to subject matter experts.
• Proven capacity to coach, inspire, and maintain high accountability with top-performing individuals.
• Regular, practical experience leveraging AI to enhance both the quality and efficiency of your work.
• Exceptional communication and relationship-building capabilities with students, families, mentors, and founders.
• Availability to work full-time on-site in New York City, including occasional travel throughout the year.
• Legal authorization to work in the United States.

Nice-to-have Requirements

• Experience founding or co-founding a business.
• Background in coaching, mentoring, or directing programs for teenagers or young adults.
• An existing network of founders, investors, operators, or mentors.
• Prior experience in early-stage startups where cross-functional responsibilities were routine.

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 $125 USD/hour, which equates to $250,000 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-5825-US-Yonkers-Entrepreneursh.001