Entrepreneurship Program Director $250,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
Shape founders, not curricula.
The conventional view is that high school prepares students for what comes next. Our perspective is different: what comes next begins immediately. Founders School operates as a four-year institution serving students unwilling to postpone meaningful work until they reach adulthood. These students aren't simulating entrepreneurship through case studies. They're establishing actual companies, collaborating with proven founders, developing AI fluency, and addressing substantive challenges. The ambition we expect reflects the ambition they bring: launch a million-dollar enterprise, pinpoint problems that demand solutions, and achieve AI mastery ahead of their elders. Your responsibility is ensuring that ambition remains viable over time.
Your function does not involve classroom instruction or prescriptive business guidance. Instead, you will coach a cohort of emerging founders on a daily basis, maintaining their accountability, helping them navigate obstacles, and sustaining momentum when the entrepreneurial path grows challenging. You will recognize the moments that call for confrontation, encouragement, or strategic introductions to mentors and resources. The curriculum framework, resident entrepreneurs, and founder network supply the technical startup knowledge. Your contribution is the steadiness, rigor, and forward motion that convert capability into achievement.
This role also represents a foundational opportunity. As part of our inaugural team in New York City, you will contribute to defining the culture, operational systems, and everyday student experience of an institution built to transform high school outcomes. Your work will extend beyond a single student group—it will inform the model for every subsequent Founders School location. If you are drawn to the startup environment, trust that elevated expectations yield elevated results, and wish to channel your effort into cultivating the next wave of entrepreneurs, we welcome your application.
What you will be doing
- Provide ongoing coaching and motivation to a cohort of student founders via weekly one-on-one sessions, daily touchpoints, and group check-ins designed to maintain measurable forward progress.
- Maintain exceptionally high standards for execution while delivering the structure and accountability that enable students to work through challenges and continue building.
- Track student advancement using FounderOS, recognize when individuals encounter friction, and facilitate connections to mentors, Entrepreneurs-in-Residence, or additional resources that catalyze development.
- Contribute to establishing the culture, rituals, programming, events, and operational cadence of a premier entrepreneurial high school.
- Accompany students on multiple annual trips while cultivating enduring relationships with founders, investors, operators, and entrepreneurial families.
What you will NOT be doing
- Serving as the lead business strategist or primary consultant on student ventures. That domain belongs to FounderOS, Entrepreneurs-in-Residence, and external mentors.
- Delivering traditional classroom instruction or evaluating academic assignments.
- Tolerating mediocre output from students whose capabilities suggest exceptional potential.
- Facilitating sessions beyond your domain of competence or defaulting to superficial startup counsel.
- Operating within an inflexible institutional framework where administrative process impedes substantive student impact.
Key responsibilities
Establish conditions under which every student advances consistently as an entrepreneur, integrating outstanding coaching, rigorous accountability, purposeful connections, and a culture that transforms ambitious adolescents into competent founders.
Candidate requirements
- A minimum of 3 years in a leadership role or high-impact capacity at a startup or rapidly scaling company.
- Solid business acumen and the confidence to interact meaningfully with early-stage founders, while understanding when to defer to specialized expertise.
- Proven capacity to coach, inspire, and enforce accountability among high-caliber individuals.
- Regular, practical use of AI tools to enhance both the quality and efficiency of your output.
- Excellent interpersonal and communication capabilities with students, families, mentors, and entrepreneurial professionals.
- Commitment to full-time, on-site work in New York City, including periodic travel during the year.
- Legal authorization to work in the United States.
Nice to have
- Experience founding or co-founding a venture.
- Background in coaching, mentoring, or program leadership focused on teenagers or emerging adults.
- An active professional network including founders, investors, operators, or advisors.
- Prior involvement in early-stage startups requiring cross-functional work across diverse responsibilities.
Applying for a role? Here’s what to expect.
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