Entrepreneurship Program Manager, Founders School

Traditional high schools define success by grades and standardized test scores. At Founders School, success is measured by businesses students launch, real problems they solve, and outcomes most adults consider out of reach for teenagers.

We're seeking someone who can challenge, motivate, and guide ambitious teenage entrepreneurs as they create real businesses, harness AI, and pursue ambitions most people reserve for adulthood.

If high standards, high ownership, and helping exceptional young people reach extraordinary results energize you, read on.

• Lead daily execution and maintain momentum across your portfolio of students through standups, coaching, and accountability frameworks.
• Deliver weekly 1:1 coaching sessions and daily check-ins that enable students to break through obstacles and sustain progress.
• Track student performance within FounderOS, catch stalled momentum early, and deploy support resources as needed.
• Link students to mentors, founders, operators, and growth opportunities that speed their development.
• Facilitate workshops, events, and community experiences that build culture and elevate performance standards.
• Demonstrate practical AI application and guide students in embedding AI into their businesses, workflows, and decision‑making.
• Accompany students on 3‑4 school trips per year.

• Offering deep strategic business consulting as students develop their ventures. That responsibility belongs to FounderOS, Entrepreneurs-in-Residence, and visiting mentors.
• Tolerating performance that falls short of a student's proven capabilities.
• Teaching academic subjects. The academic platform and academic team handle that experience.
• Leading workshops beyond your area of expertise.
• Providing generic resources or introductions that don't align with Founders School standards.

Build the culture, accountability structures, and support systems that allow ambitious student founders to execute consistently, use AI effectively, and deliver outcomes that exceed what traditional education enables.

• 3+ years in leadership or high‑impact individual contributor positions at startups, growth‑stage companies, or similarly rigorous environments.
• The capacity to participate meaningfully in entrepreneurial discussions and recognize when to bring in specialized expertise.
• A clear strength beyond coaching: workshop facilitation, event design, content creation, community building, relationship development, or another equally valuable skill.
• The ability to hold the attention of ambitious teenagers and build an environment they're excited to join.
• The ability to provide tough feedback in ways that boost motivation and performance.
• Active daily use of AI tools with concrete examples of how AI enhances your work.
• Willingness to work on‑site in New York City (relocation support available).
• Authorization to work in the United States.

• Founded or co‑founded a business.
• Experience coaching, mentoring, or running programs for teenagers or young adults.
• An established network of founders, operators, investors, or mentors.
• Early‑stage startup experience where you juggled multiple roles and built 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, and master AI before adults do.

Launching in NYC Fall 2026.

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.