By the conclusion of your first year, you will understand each of your students intimately: their capabilities, development areas, drivers, and aspirations. The school will possess a culture, a cadence, and a benchmark for excellence. Much of it will reflect your influence.
As Founders School grows from New York into other cities, opportunities multiply. That could mean managing future guides, supporting new campus launches, or ultimately operating a campus as Head of School. These opportunities are earned through demonstrated impact, not longevity. You will also cultivate relationships with founders, investors, operators, and entrepreneurial families who join the Founders School ecosystem. These relationships frequently extend well beyond the educational setting.
Entrepreneurship Program Manager $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
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 will NOT 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.
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.
Candidate 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
- 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.
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
Frequently asked questions
What you will learn
Work examples
- A student begins cruising after initial success. You spot the trend rapidly, recalibrate expectations, and guide them back toward sustained execution.
- A student hesitates before their first sales conversation. You assist with preparation, practice the pitch, and help them enter confidently.
- A student requires a particular resource or mentor. You understand who to engage, why the connection matters, and how to structure it effectively.
- A cohort loses momentum during a challenging build phase. You facilitate a targeted session that revives energy and reinforces standards.
Reviews
Meet some people who've landed similar jobs
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
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AI-first remote workers.