Within your first year, you will develop deep familiarity with each student in your portfolio: their capabilities, development opportunities, drivers, and ambitions. The school will establish a culture, cadence, and benchmark for excellence. Much of that foundation will reflect your contributions.
As Founders School grows from New York to other cities, your opportunities will broaden correspondingly. This could mean guiding future program directors, supporting new campus launches, or ultimately serving as Head of School for a location. These pathways open based on demonstrated results, not time served. You will also cultivate connections with founders, investors, operators, and entrepreneurial families integrated into the Founders School network. These relationships frequently extend well beyond the academic setting.
Youth Entrepreneurship Program Director $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 test results. At Founders School, success is defined by companies started, real-world problems addressed, and students accomplishing what most adults would view as unattainable.
We seek a leader capable of inspiring, pushing, and guiding driven teenage entrepreneurs as they launch actual businesses, become proficient in AI, and tackle ambitions most reserve for later in life.
If high expectations, significant autonomy, and empowering remarkable young individuals to deliver exceptional results excites you, read on.
What you will be doing
- Propel day-to-day execution and forward momentum within your assigned student cohort using standups, one-on-one coaching, and structured accountability.
- Lead weekly individual coaching conversations and daily touchpoints that enable students to navigate challenges and sustain forward progress.
- Track student activity in FounderOS, detect slowdowns or barriers early, and orchestrate the appropriate support interventions.
- Facilitate connections between students and mentors, founders, operators, and other growth-accelerating opportunities.
- Organize and deliver workshops, events, and communal experiences that deepen culture and elevate performance expectations.
- Demonstrate hands-on AI application and guide students in integrating AI across their ventures, operations, and decision frameworks.
- Accompany students on 3-4 school trips annually.
What you will NOT be doing
- Delivering advanced strategic business advisory as students scale their ventures. That function belongs to FounderOS, Entrepreneurs-in-Residence, and guest mentors.
- Tolerating output that sits below a student's proven capacity.
- Instructing traditional academic coursework. Our academic platform and faculty handle that domain.
- Facilitating workshops in areas outside your competency.
- Offering generic or low-value resources and introductions inconsistent with Founders School quality standards.
Key responsibilities
Build the culture, accountability frameworks, and support infrastructure that empower motivated student founders to execute reliably, apply AI with skill, and achieve results that exceed the boundaries of conventional education.
Candidate requirements
- 3+ years in leadership positions or high-impact individual contributor capacities within startups, scaling companies, or comparably rigorous settings.
- Comfort participating in entrepreneurial discussions and discernment about when specialized expertise should be engaged.
- A standout capability beyond coaching: workshop design, event orchestration, content development, community cultivation, network expansion, or another equally impactful skill.
- The presence to capture the focus of ambitious teenagers and cultivate an environment they are motivated to join.
- The skill to communicate challenging feedback in ways that elevate both drive and results.
- Regular use 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.
Nice to have
- Founded or co-founded a company.
- Background coaching, mentoring, or running programs for teenagers or young adults.
- An established network of founders, operators, investors, or mentors.
- Experience at early-stage startups where you handled diverse responsibilities 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 underperforming after initial success. You spot the trend immediately, recalibrate their expectations, and guide them back to sustained execution.
- A student hesitates before their first sales conversation. You support their preparation, run rehearsals, and ensure they approach it with assurance.
- A student requires a particular resource or mentor connection. You identify the right person, understand the strategic value, and structure the introduction for maximum impact.
- A cohort experiences declining motivation during a challenging development phase. You facilitate a targeted intervention that reignites momentum and elevates standards.
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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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