By the end of year one, you will know every one of your students deeply: their strengths, growth areas, motivations, and goals. The school will have a culture, a rhythm, and a standard of excellence. Much of it will carry your fingerprints.
As Founders School expands from New York into additional cities, opportunities expand as well. That may mean leading future guides, helping launch new campuses, or eventually running a campus as Head of School. Those opportunities are earned through impact, not tenure. You will also build relationships with founders, investors, operators, and entrepreneurial families who become part of the Founders School community. Those relationships often extend far beyond the classroom.
High School Elite Guide - Entrepreneurship $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
New York City, NY, US
In-person
full-time (40 hrs/week)
Flexible schedule
Long-term role
Description
Most high schools measure success through grades and test scores. Founders School measures success through businesses launched, problems solved, and students who achieve outcomes most adults would consider impossible.
We're looking for someone who can motivate, challenge, and develop ambitious teenage founders as they build real companies, master AI, and pursue goals most people wouldn't attempt until adulthood.
If you're energized by high standards, high ownership, and helping exceptional young people achieve extraordinary outcomes, keep reading.
What you will be doing
- Drive daily execution and momentum across your student portfolio through standups, coaching sessions, and accountability systems.
- Conduct weekly 1:1 coaching sessions and daily check-ins that help students overcome obstacles and maintain progress.
- Monitor student performance in FounderOS, identify stalled progress early, and coordinate support resources when needed.
- Connect students with mentors, founders, operators, and opportunities that accelerate growth.
- Run workshops, events, and community experiences that strengthen culture and raise performance standards.
- Model practical AI usage and help students incorporate AI into their businesses, workflows, and decision-making processes.
- Travel with students on 3-4 school trips each year.
What you will NOT be doing
- Providing deep strategic business consulting as students build their companies. FounderOS, Entrepreneurs-in-Residence, and visiting mentors own that responsibility.
- Accepting performance that falls below a student's demonstrated potential.
- Teaching academic subjects. The academic platform and academic team own that experience.
- Running workshops outside your area of expertise.
- Sharing generic resources or introductions that don't meet Founders School standards.
Key responsibilities
Create the culture, accountability, and support systems that enable ambitious student founders to consistently execute, leverage AI effectively, and achieve outcomes beyond what traditional education makes possible.
Candidate requirements
- 3+ years in leadership or high-impact individual contributor roles within startups, growth-stage companies, or similarly demanding environments.
- The ability to engage comfortably in entrepreneurial conversations and know when to bring in deeper expertise.
- A distinctive strength beyond guiding: workshop facilitation, event design, content creation, community building, relationship development, or something equally valuable.
- The ability to command the attention of ambitious teenagers and create an environment they want to be part of.
- The ability to deliver difficult feedback in a way that increases motivation and performance.
- Daily use of AI tools with clear examples of how AI improves your work.
- Willingness to work on-site in New York City (relocation support provided).
- Authorization to work in the United States.
Nice to have
- Founded or co-founded a business.
- Experience coaching, mentoring, or leading programs for teenagers or young adults.
- An existing network of founders, operators, investors, or mentors.
- Early-stage startup experience where you wore multiple hats and built systems from scratch.
How it works
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.
STEP 1
Chat-style
screening interview.
STEP 2
Cognitive 
aptitude test.
STEP 3
Prove real-world 
job skills.
STEP 4
Interview with the hiring manager.
STEP 5
Pass
proctored test.
STEP 6
Accept job offer.
Frequently asked questions
What you will learn
Work examples
- A student starts coasting after an early win. You identify the pattern quickly, reset expectations, and coach them back into consistent execution.
- A student gets stuck before a first sales call. You help them prepare, rehearse, and walk in with confidence.
- A student needs a specific resource or mentor. You know who to pull in, why it matters, and how to make the connection useful.
- A group loses energy during a difficult build cycle. You run a focused session that restores momentum and raises the standard.
Reviews
Meet some people who've landed similar jobs
Why Crossover
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.
Join the world's largest community of 
AI-first remote workers.