After one year, you will understand each of your students comprehensively: capabilities, development needs, driving forces, and ambitions. The school will possess a distinct culture, operational cadence, and performance benchmark. Significant portions will reflect your direct influence.
As Founders School scales beyond New York to additional metropolitan areas, career paths broaden correspondingly. This could include managing future coaching staff, supporting new campus launches, or ultimately overseeing a location as Head of School. Such advancement stems from demonstrated results, not time served. You will also cultivate connections with founders, investors, operators, and entrepreneurial families integrated into the Founders School ecosystem. These relationships frequently persist well beyond student graduation.
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
Description
Traditional high schools define success by grades and standardized test performance. At Founders School, success is defined by companies students launch, real problems they solve, and achievements that would seem impossible to most adults.
We need someone capable of pushing, inspiring, and guiding ambitious teenage entrepreneurs as they create functioning businesses, harness AI tools, and chase goals typically reserved for those much older.
If high expectations, significant autonomy, and supporting exceptional students toward remarkable results excites you, continue reading.
What you will be doing
- Propel daily progress and execution momentum for your assigned student cohort using standups, structured coaching, and accountability frameworks.
- Lead weekly one-on-one coaching conversations and frequent check-ins designed to help students move past roadblocks and sustain forward motion.
- Track student activity within FounderOS, catch stagnation early, and bring in additional support when circumstances require it.
- Build bridges between students and mentors, founders, operators, and growth opportunities that speed development.
- Facilitate workshops, events, and community-building activities that deepen culture and elevate performance expectations.
- Demonstrate real-world AI application and guide students in embedding AI throughout their ventures, systems, and strategic thinking.
- Accompany students on 3-4 school trips annually.
What you will NOT be doing
- Delivering in-depth strategic business advisory as students develop their ventures. That function belongs to FounderOS, Entrepreneurs-in-Residence, and guest mentors.
- Tolerating work quality beneath what a student has proven capable of achieving.
- Instructing traditional academic coursework. The academic platform and its dedicated team manage that domain.
- Leading workshops in areas outside your demonstrated competence.
- Offering generic contacts or materials that fail to meet Founders School quality benchmarks.
Key responsibilities
Establish the cultural norms, accountability mechanisms, and support infrastructure that empower driven student entrepreneurs to execute reliably, apply AI strategically, and reach results that traditional schooling cannot deliver.
Candidate requirements
- 3+ years in leadership positions or high-impact individual contributor capacities at startups, scaling companies, or equivalently rigorous settings.
- Comfort participating in entrepreneurial discussions and judgment about when specialized expertise is needed.
- A clear standout capability beyond coaching: workshop design, event execution, content production, community cultivation, network expansion, or another comparably useful skill.
- Capacity to capture and hold the focus of ambitious adolescents and build an environment they actively seek.
- Skill in providing hard feedback that raises both drive and output.
- Routine application of AI technologies with concrete demonstrations of productivity gains from AI integration.
- Readiness to work on-site at our New York City location (relocation assistance available).
- Legal authorization for employment in the United States.
Nice to have
- Started or helped start a company.
- Background in coaching, mentorship, or program leadership focused on teenagers or emerging adults.
- Established network spanning founders, operators, investors, or advisors.
- Early-stage venture experience requiring diverse responsibilities and ground-up system creation.
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 following initial success. You spot the behavior immediately, recalibrate standards, and guide them toward renewed consistent performance.
- A student hesitates before their inaugural sales conversation. You assist with preparation, conduct role-play, and enable them to proceed confidently.
- A student requires a particular resource or advisor. You understand precisely whom to engage, the strategic rationale, and how to structure a productive introduction.
- A cohort experiences flagging motivation during a challenging development phase. You deliver a targeted intervention that recovers momentum and elevates expectations.
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