Startup Coach $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
Develop young founders, not curricula.
Most assume high school exists to ready students for what comes next. We believe what comes next begins today. Founders School is a four-year institution for students unwilling to postpone building meaningful work until they reach adulthood. Our students aren't working through simulated business assignments. They're creating actual companies, collaborating with proven entrepreneurs, becoming fluent in AI, and tackling challenges that have real stakes. Our expectations are elevated because our students are exceptional: launch a million-dollar enterprise, pinpoint problems that deserve attention, and command AI before most adults catch up. Your responsibility is to make that level of ambition achievable and enduring.
You won't deliver traditional instruction or dictate how students should operate their ventures. You'll guide a cohort of emerging founders daily, ensuring they maintain accountability, navigate obstacles, and sustain momentum when entrepreneurship becomes challenging. You'll recognize the right moments to push them harder, offer encouragement, or introduce them to the appropriate mentor or tool. The structured content, Entrepreneurs-in-Residence, and founder ecosystem deliver the technical startup knowledge. You deliver the steady presence, rigorous standards, and forward motion that convert promise into tangible outcomes.
This role also presents a chance to contribute to something being built from inception. As part of our founding team in New York City, you'll influence the culture, operating systems, and lived experience of an institution created to transform what secondary education can deliver. Your contributions won't be limited to a single student cohort. They will inform the model for every Founders School location that opens afterward. If you're drawn to entrepreneurship, trust that ambitious standards yield remarkable results, and are ready to channel your effort into cultivating the next wave of founders, we want to hear from you.
What you will be doing
- Guide and inspire a cohort of student entrepreneurs through weekly one-on-one sessions, daily touchpoints, and team stand-ups that ensure consistent, measurable advancement.
- Maintain exceptionally high performance standards while delivering the structured support and accountability students require to work through challenges and continue making progress.
- Track student development via FounderOS, recognize when individuals encounter roadblocks, and link them with mentors, Entrepreneurs-in-Residence, or additional resources to drive their growth forward.
- Contribute to shaping the culture, rituals, programming, events, and operational cadence of an elite entrepreneurial secondary school.
- Accompany students on multiple trips annually while cultivating enduring connections with founders, investors, business operators, and entrepreneurial families.
What you will NOT be doing
- Serving as the main business strategist or crafting startup plans for students. FounderOS, Entrepreneurs-in-Residence, and guest mentors fulfill that function.
- Delivering conventional academic instruction or evaluating traditional coursework.
- Tolerating mediocre output from students with the capacity for outstanding work.
- Facilitating workshops in areas beyond your skill set or defaulting to surface-level entrepreneurial guidance.
- Operating within an inflexible institutional framework where administrative obstacles interfere with student success.
Key responsibilities
Build an environment in which every student advances continuously as an entrepreneur through a combination of skilled coaching, rigorous accountability, strategic 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 position at a startup or rapidly scaling company.
- Sound business acumen and the confidence to interact meaningfully with early-stage entrepreneurs while recognizing when specialized expertise is needed.
- Proven capability to coach, inspire, and maintain accountability with high-performing people.
- Regular, practical use of AI tools to enhance both the quality and efficiency of your output.
- Excellent communication and interpersonal abilities when working with students, families, mentors, and entrepreneurs.
- Availability to work full-time on-site in New York City, including occasional travel during the year.
- Legal authorization to work in the United States.
Nice to have
- Founded or co-founded a company.
- Background in coaching, mentoring, or managing programs designed for teenagers or young adults.
- A developed network of entrepreneurs, investors, business operators, or mentors.
- Track record in early-stage ventures where you routinely handled responsibilities across several disciplines.
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
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The Olympics of work
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Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
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