Startup Program Manager, Founders School - $200,000​/year USD

Traditional high schools track achievement via grades and standardized test results. Founders School defines success differently: by the businesses students launch, the problems they solve, and the results they deliver that most adults would find improbable.

We seek someone capable of motivating, challenging, and guiding ambitious teenage entrepreneurs as they launch genuine companies, harness AI tools, and pursue ambitions typically reserved for much later in life.

If high expectations, significant autonomy, and supporting exceptional young people to reach remarkable outcomes excites you, read on.

• Lead daily execution and forward progress across your assigned student group using standups, coaching conversations, and structured accountability.
• Facilitate weekly one-on-one coaching and daily touchpoints that enable students to navigate challenges and sustain momentum.
• Track student activity within FounderOS, spot early signs of stagnation, and bring in the right support when necessary.
• Link students with mentors, experienced founders, operators, and growth opportunities that speed their development.
• Organize workshops, events, and shared experiences that deepen culture and elevate performance expectations.
• Demonstrate effective AI application and guide students in integrating AI into their ventures, systems, and thinking.
• Accompany students on 3-4 school trips annually.

• Delivering in-depth strategic business advice as students develop their ventures. That domain belongs to FounderOS, Entrepreneurs-in-Residence, and guest mentors.
• Tolerating work that under performs a student's proven capability.
• Instructing traditional academic coursework. Our academic platform and teaching staff manage that function.
• Facilitating workshops beyond your core competencies.
• Offering generic materials or connections that fail to meet the school's quality threshold.

Build the culture, accountability frameworks, and support infrastructure that allow driven student founders to execute reliably, apply AI strategically, and deliver results that surpass what conventional education typically enables.

• At least 3 years in leadership positions or high-impact contributor roles at startups, scaling organizations, or comparably rigorous settings.
• Comfort participating in entrepreneurial discussions and discernment about when specialized expertise is required.
• A specialized capability beyond coaching: workshop design, event orchestration, content development, community cultivation, network expansion, or another high-value skill.
• The presence to hold the focus of driven teenagers and build an environment they find compelling.
• The skill to communicate challenging feedback in ways that strengthen drive and results.
• Regular application of AI tools with concrete demonstrations of how AI enhances your output.
• Availability to work on-site in New York City (relocation assistance available).
• Legal authorization to work in the United States.

• Launched or co-launched a company.
• Background in coaching, mentoring, or managing programs for adolescents or emerging adults.
• Established connections among founders, operators, investors, or mentors.
• Experience in early-phase startups where you handled diverse responsibilities and created processes 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.

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-Stamford-Startup Program.
002