Startup Coach, Founders School - $250,000/year USD at Crossover

Develop founders, not curricula.

Most assume high school exists to prepare students for what's ahead. We believe what's ahead begins today. Founders School is a four-year high school built for students unwilling to postpone building something significant until they're older. These students aren't simulating entrepreneurship through hypothetical assignments. They're starting real ventures, collaborating with seasoned founders, becoming fluent in AI, and addressing challenges that have genuine impact. Our expectations are elevated because our students are elevated: launch a million-dollar company, uncover problems that demand solutions, and achieve AI mastery ahead of most adults. Your responsibility is to make that ambition endure.

You won't deliver traditional lessons or prescribe business tactics to students. Instead, you'll coach a cohort of young entrepreneurs daily, ensuring they remain accountable, navigate challenges, and maintain momentum when company-building becomes demanding. You'll recognize when to push them, when to support them, and when to introduce them to the appropriate mentor or tool. The structured curriculum, Entrepreneurs-in-Residence, and founder ecosystem deliver the tactical startup knowledge. You deliver the continuity, rigor, and forward motion that convert promise into performance.

This role also represents a chance to co-create something foundational. As part of our founding team in New York City, you'll contribute to shaping the culture, operational systems, and lived experience of a school designed to transform what high school graduates can accomplish. Your contributions won't only influence one student group. They will inform the framework for every future Founders School location. If you're drawn to the startup world, believe that ambitious standards drive ambitious results, and are ready to channel your effort into cultivating the next wave of entrepreneurs, we want to hear from you.

What You Will Be Doing

• Guide and inspire a group of student founders via weekly one-on-one sessions, daily progress touchpoints, and collective stand-ups that ensure consistent, tangible advancement.
• Maintain an exceptionally high standard for performance while delivering the guidance and accountability necessary for students to clear roadblocks and continue building.
• Track student development using FounderOS, recognize when learners encounter friction, and facilitate introductions to mentors, Entrepreneurs-in-Residence, or additional resources that catalyze their trajectory.
• Contribute to establishing the culture, rituals, programming, events, and operational cadence of an elite entrepreneurial high school.
• Accompany students on multiple trips annually while cultivating enduring connections with founders, investors, operators, and entrepreneurial communities.

What You Won’t Be Doing

• Serving as the lead business advisor or crafting company strategy for students. That domain belongs to FounderOS, Entrepreneurs-in-Residence, and guest mentors.
• Conducting conventional academic instruction or evaluating traditional coursework.
• Tolerating mediocre output from students who possess the capacity for excellence.
• Facilitating sessions beyond your skill set or defaulting to surface-level entrepreneurial guidance.
• Operating within an inflexible institutional framework where administrative processes impede student success.

Startup Coach Key Responsibilities

Build an environment in which each student reliably advances as an entrepreneur by integrating outstanding coaching, rigorous accountability, strategic connections, and a culture that transforms ambitious adolescents into competent founders.

Basic Requirements

• A minimum of 3 years in a leadership or high-impact role at a startup or rapidly scaling company.
• Solid business acumen and the confidence to interact with early-stage entrepreneurs while understanding when to defer to specialized experts.
• Proven capacity to coach, inspire, and maintain accountability among high-performing individuals.
• Routine, practical use of AI to enhance both the quality and efficiency of your output.
• Exceptional communication and interpersonal abilities with students, families, mentors, and entrepreneurs.
• Commitment to full-time, in-person work in New York City, with periodic travel during the year.
• Legal authorization to work in the United States.

Nice-to-have Requirements

• Founded or co-founded your own company.
• Background in coaching, mentoring, or managing initiatives for teenagers or emerging adults.
• A developed network of entrepreneurs, investors, operators, or advisors.
• History working in early-stage ventures where you frequently handled diverse responsibilities.

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-Paterson-StartupCoach