Entrepreneurship Coach, Founders School

Traditional high schools define success by grades and standardized test results. At Founders School, success is defined by companies created, real problems addressed, and students accomplishing what most adults believe impossible.

We need someone capable of inspiring, pushing, and coaching driven teenage entrepreneurs as they launch actual businesses, become proficient with AI, and work toward ambitions typically reserved for adulthood.

If high expectations, deep ownership, and guiding talented young people toward remarkable results energizes you, continue reading.

• Push daily execution and forward motion across your assigned student group using standups, coaching conversations, and accountability frameworks.
• Lead weekly one‑on‑one coaching meetings and daily touchpoints that enable students to work through challenges and sustain momentum.
• Track student activity in FounderOS, spot slowing progress quickly, and bring in support resources as necessary.
• Link students to mentors, operators, founders, and opportunities that speed up their development.
• Organize workshops, events, and community activities that deepen culture and elevate performance expectations.
• Demonstrate hands‑on AI application and guide students in integrating AI into their operations, systems, and strategic thinking.
• Accompany students on 3‑4 school trips annually.

• Offering in‑depth strategic business advice as students develop their ventures; that responsibility belongs to FounderOS, Entrepreneurs‑in‑Residence, and external mentors.
• Tolerating output that sits below a student's proven capability.
• Instructing traditional academic coursework; the academic platform and teaching staff manage that function.
• Leading workshops on topics outside your skill set.
• Distributing low‑quality resources or introductions inconsistent with Founders School expectations.

Build the culture, accountability structures, and support infrastructure that allow motivated student founders to execute reliably, apply AI strategically, and deliver results that exceed what conventional education enables.

• 3+ years in leadership positions or high‑impact contributor roles at startups, scaling companies, or comparably rigorous settings.
• Comfort participating in entrepreneurial discussions and recognizing when specialized expertise is required.
• A proven strength beyond coaching: workshop design, event planning, content production, community engagement, network building, or another equally impactful skill.
• The capacity to hold the focus of ambitious teenagers and build an environment they are drawn to.
• The skill to provide tough feedback in ways that strengthen drive and results.
• Regular use of AI tools with concrete examples showing how AI enhances your output.
• Readiness to work on‑site in New York City (relocation assistance available).
• Legal authorization to work in the United States.

• Founded or helped launch a company.
• Background coaching, mentoring, or running programs aimed at teenagers or emerging adults.
• A developed network of founders, business operators, investors, or mentors.
• Experience at early‑stage startups where you handled varied responsibilities and created systems from the ground up.

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!

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  for more details on this topic.

Crossover Job Code: LJ-5816-US-Connecti-Entrepreneur sh