By the conclusion of your first year, you will understand each of your students intimately: their capabilities, development needs, drivers, and ambitions. The school will possess a culture, cadence, and benchmark of excellence. Much of it will reflect your influence.
As Founders School grows from New York to other cities, new opportunities will emerge. That could include managing future guides, launching additional campuses, or ultimately operating a campus as Head of School. These opportunities are earned based on results, not seniority. You will also cultivate connections with founders, investors, operators, and entrepreneurial families within the Founders School ecosystem. These relationships frequently extend well beyond the program itself.
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
Description
Traditional high schools evaluate students based on test scores and GPA. At Founders School, success is measured by businesses created, real problems solved, and students accomplishing what most adults would consider unattainable.
We're seeking an individual who can inspire, push, and guide ambitious teenage entrepreneurs as they launch actual companies, adopt AI, and tackle challenges most people defer until their twenties or beyond.
If high expectations, significant autonomy, and empowering exceptional youth to reach extraordinary milestones excites you, continue reading.
What you will be doing
- Lead daily execution and forward momentum for your student cohort using standups, coaching conversations, and structured accountability systems.
- Facilitate weekly 1:1 coaching and daily check-ins to help students navigate roadblocks and sustain their progress.
- Track student activity in FounderOS, spot slowing momentum early, and mobilize support resources as necessary.
- Link students with mentors, founders, operators, and growth opportunities that speed their development.
- Organize workshops, events, and community activities that deepen culture and elevate performance standards.
- Demonstrate practical AI application and support students in integrating AI into their businesses, workflows, and decision-making.
- Accompany students on 3-4 school trips annually.
What you will NOT be doing
- Delivering in-depth strategic business advisory as students scale their ventures. That responsibility belongs to FounderOS, Entrepreneurs-in-Residence, and visiting mentors.
- Tolerating results that fall short of a student's proven capabilities.
- Instructing academic coursework. That experience is owned by the academic platform and faculty.
- Facilitating workshops beyond your domain of expertise.
- Making low-value introductions or sharing generic resources inconsistent with Founders School standards.
Key responsibilities
Build the culture, accountability frameworks, and support infrastructure that enable ambitious student founders to execute consistently, apply AI with confidence, and deliver outcomes that exceed what conventional education systems allow.
Candidate requirements
- 3+ years in leadership or high-impact individual contributor positions at startups, growth-stage companies, or similarly rigorous settings.
- The capacity to participate confidently in entrepreneurial discussions and recognize when specialized expertise should be engaged.
- A specific strength beyond coaching: workshop design, event execution, content development, community activation, relationship cultivation, or a similarly impactful skill.
- The capacity to earn the attention of ambitious teenagers and build an environment they are drawn to.
- The capacity to provide candid, challenging feedback that elevates motivation and results.
- Active daily use of AI tools with concrete examples of how AI enhances your productivity.
- Availability to work on-site in New York City (relocation assistance available).
- Legal authorization to work in the United States.
Nice to have
- Started or co-founded a business.
- Background coaching, mentoring, or leading initiatives for teenagers or young adults.
- Established network of founders, operators, investors, or mentors.
- Early-stage startup background where you managed multiple roles 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 becomes complacent after achieving an early success. You spot the shift quickly, recalibrate expectations, and guide them toward sustained execution.
- A student hesitates before making their first sales call. You support them in preparation, rehearsal, and entering the conversation with confidence.
- A student requires a particular resource or mentor. You identify the right person, understand the relevance, and facilitate a meaningful introduction.
- A cohort loses momentum during a challenging development phase. You lead a targeted session that reignites drive and raises the bar.
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The Olympics of work
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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
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