Entrepreneurship Coach, Founders School - $200,000/year USD at Crossover

Traditional high schools define success by grades and standardized test performance. At Founders School, success is defined by launched ventures, solved problems, and students accomplishing what most adults would deem unattainable.

We seek someone capable of inspiring, challenging, and guiding driven teenage entrepreneurs as they create functioning businesses, harness AI capabilities, and pursue ambitions most defer until adulthood.

If high expectations, significant ownership, and supporting remarkable young individuals to reach exceptional results excite you, continue reading.

What You Will Be Doing

• Propel daily execution and progress across your assigned student cohort through standups, coaching interactions, and accountability frameworks.
• Lead weekly one-on-one coaching conversations and daily touchpoints that enable students to navigate challenges and sustain forward momentum.
• Track student activity in FounderOS, detect stagnation early, and mobilize support resources as necessary.
• Facilitate connections between students and mentors, founders, operators, and opportunities that catalyze advancement.
• Organize workshops, gatherings, and community initiatives that reinforce culture and elevate performance benchmarks.
• Demonstrate hands-on AI application and guide students in embedding AI into their ventures, workflows, and decision frameworks.
• Accompany students on 3-4 school trips annually.

What You Won’t Be Doing

• Delivering in-depth strategic business advisory as students develop their ventures. FounderOS, Entrepreneurs-in-Residence, and visiting mentors fulfill that function.
• Tolerating performance beneath a student's proven capabilities.
• Instructing academic coursework. The academic platform and academic faculty manage that domain.
• Facilitating workshops beyond your specialty areas.
• Offering generic resources or introductions that fail to satisfy Founders School quality expectations.

Entrepreneurship Coach Key Responsibilities

Establish the culture, accountability infrastructure, and support mechanisms that empower ambitious student founders to execute reliably, utilize AI strategically, and produce outcomes exceeding what conventional education allows.

Basic Requirements

• 3+ years in leadership positions or high-impact individual contributor capacities within startups, growth-stage organizations, or comparably rigorous settings.
• Comfort participating in entrepreneurial discussions and recognizing when to involve specialized expertise.
• A unique competency beyond coaching: workshop design, event curation, content development, community cultivation, relationship building, or another equally impactful skill.
• The capacity to capture the focus of ambitious teenagers and foster an environment they are eager to join.
• The capability to provide challenging feedback that enhances motivation and output.
• Consistent use of AI tools with concrete examples demonstrating how AI elevates your productivity.
• Willingness to work on-site in New York City (relocation assistance available).
• Work authorization for the United States.

Nice-to-have Requirements

• Founded or co-founded a company.
• Background coaching, mentoring, or managing programs for teenagers or young adults.
• An established network of founders, operators, investors, or mentors.
• Early-stage startup exposure where you handled diverse responsibilities and created systems from the ground up.

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 $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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5816-US-Stamford-Entrepreneursh.003