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

Job in Stamford, Fairfield County, Connecticut, 06925, USA
Listing for: Crossover
Full Time position
Listed on 2026-08-15
Job specializations:
  • Education / Teaching
    Business Administration
Salary/Wage Range or Industry Benchmark: 200000 USD Yearly USD 200000.00 YEAR
Job Description & How to Apply Below

Traditional high schools track success with grades and standardized tests. Founders School tracks success through launched ventures, solved problems, and students accomplishing what most adults would call impossible.

We need someone capable of motivating, challenging, and cultivating ambitious teenage entrepreneurs as they launch real businesses, harness AI, and chase ambitions most people delay until adulthood.

If high standards, significant ownership, and guiding exceptional young people toward extraordinary results energize you, continue reading.

What You Will Be Doing
  • Propel daily execution and forward momentum across your assigned student cohort via standups, coaching conversations, and accountability frameworks.
  • Lead weekly one-on-one coaching sessions and daily touchpoints that enable students to clear roadblocks and sustain forward progress.
  • Track student performance within FounderOS, detect stagnation early, and mobilize support resources as needed.
  • Link students with mentors, founders, operators, and growth opportunities that drive acceleration.
  • Facilitate workshops, events, and community gatherings that deepen culture and elevate performance expectations.
  • Demonstrate practical AI application and guide students in embedding AI into their ventures, workflows, and decision-making.
  • Accompany students on 3-4 school trips annually.
What You Won’t Be Doing
  • Delivering advanced strategic business consulting as students scale their companies. FounderOS, Entrepreneurs-in-Residence, and guest mentors handle that function.
  • Tolerating performance beneath a student's proven capability.
  • Teaching traditional academic subjects. The academic platform and instructional team manage that domain.
  • Leading workshops beyond your domain of expertise.
  • Offering generic resources or connections that fail to meet Founders School quality standards.
Entrepreneurship Program Manager

Key Responsibilities

Build the culture, accountability structures, and support infrastructure that empower ambitious student founders to execute consistently, apply AI effectively, and reach outcomes that surpass what conventional education delivers.

Basic Requirements
  • 3+ years in leadership positions or high-impact individual contributor roles at startups, growth-stage companies, or equivalently rigorous settings.
  • The capacity to participate confidently in entrepreneurial discussions and recognize when to engage specialized expertise.
  • A unique capability beyond coaching: workshop design, event orchestration, content development, community cultivation, relationship building, or comparable value-add.
  • The presence to capture the attention of ambitious teenagers and build an environment they're excited to join.
  • The skill to provide challenging feedback in ways that elevate motivation and outcomes.
  • Active daily use of AI tools with concrete examples of how AI enhances your productivity.
  • Willingness to work on-site in New York City (relocation assistance available).
  • Authorization to work in the United States.
Nice-to-have Requirements
  • Founded or co-founded a business.
  • Background 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 managed multiple functions 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.

Working with us

This is a full-time, W2 employee position with immediate access to benefits (). All roles are year-long positions. The compensation level for this role is $200,000 USD/year. The payment period is weekly. Consult  for more details on this topic.

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