Within your first year, you will understand each of your students intimately: their capabilities, development areas, drivers, and ambitions. The school will possess a culture, a cadence, and a standard of excellence. Much of that foundation will reflect your influence.
As Founders School scales from New York to new cities, your opportunities expand correspondingly. This could mean leading other guides, supporting new campus launches, or eventually operating a campus as Head of School. These opportunities are earned through demonstrated impact, not time served. You will also cultivate relationships with founders, investors, operators, and entrepreneurial families who join the Founders School ecosystem. These connections frequently extend well beyond the academic setting.
Entrepreneurship Coach $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 define success by grades and standardized test scores. At Founders School, success is defined by businesses launched, real problems solved, and students achieving what most adults would deem impossible.
We seek someone capable of motivating, challenging, and developing ambitious teenage entrepreneurs as they launch actual companies, harness AI, and pursue ambitions typically reserved for adulthood.
If high standards, high ownership, and guiding exceptional young people toward extraordinary results energize you, read on.
What you will be doing
- Propel daily execution and momentum across your assigned student portfolio via standups, coaching conversations, and accountability frameworks.
- Lead weekly 1:1 coaching sessions and daily check-ins that enable students to navigate obstacles and sustain forward progress.
- Track student performance within FounderOS, spot stagnation early, and mobilize support resources as necessary.
- Facilitate connections between students and mentors, founders, operators, and growth opportunities.
- Design and deliver workshops, events, and community experiences that elevate culture and performance expectations.
- 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 consulting as students develop their ventures. 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 academic team manage that domain.
- Facilitating workshops beyond your domain of expertise.
- Offering generic resources or introductions that fail to meet Founders School quality standards.
Key responsibilities
Establish the culture, accountability structures, and support mechanisms that allow ambitious student founders to execute consistently, use AI strategically, and deliver outcomes that exceed traditional educational frameworks.
Candidate requirements
- 3+ years in leadership roles or high-impact individual contributor positions at startups, growth-stage companies, or similarly rigorous environments.
- Comfort engaging in entrepreneurial discussions and discernment to escalate when specialized expertise is required.
- A unique capability beyond coaching: workshop design, event production, content development, community cultivation, network building, or another high-value skill.
- Capability to capture the focus of ambitious teenagers and foster an environment they are eager to join.
- Skill in delivering challenging feedback that enhances motivation and elevates performance.
- Daily application of AI tools with concrete examples of how AI enhances your output.
- Readiness 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 company.
- Background coaching, mentoring, or directing programs for teenagers or young adults.
- Established network of founders, operators, investors, or mentors.
- Early-stage startup tenure where you managed multiple 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 coasting following an initial success. You detect the trend swiftly, recalibrate expectations, and guide them back to consistent performance.
- A student hesitates before their first sales conversation. You assist with preparation, conduct rehearsal, and ensure they approach with confidence.
- A student requires a particular resource or mentor. You understand whom to engage, the strategic rationale, and how to structure a valuable introduction.
- A cohort loses momentum during a challenging development phase. You facilitate a targeted session that restores drive and elevates standards.
Reviews
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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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