Lead Founder Guide
$250,000 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

Lead Founder Guide   $250,000 USD/year

Description

Build entrepreneurs, not lesson plans.

Most people think high school is about preparing students for the future. We think the future starts now. Founders School is a four-year high school for students who refuse to wait until adulthood to build something meaningful. Our students aren't completing hypothetical business projects. They're launching real companies, working with accomplished founders, mastering AI, and solving problems that matter. Our commitment is ambitious because our students are ambitious: build a million-dollar business, identify problems worth solving, and master AI before adults do. Your role is to make that ambition sustainable.

You won't be teaching classes or telling students how to run their businesses. You'll coach a group of young founders every day, helping them stay accountable, overcome setbacks, and keep moving forward when building a company gets difficult. You'll know when to challenge them, when to encourage them, and when to connect them with the right mentor or resource. The curriculum, Entrepreneurs-in-Residence, and founder network provide the startup expertise. You provide the consistency, standards, and momentum that turn potential into results.

This is also an opportunity to help build something from the ground up. As a member of our founding team in New York City, you'll help shape the culture, systems, and daily experience of a school designed to redefine what high school can produce. The work you do won't just impact one group of students. It will become part of the blueprint for every Founders School campus that follows. If you're energized by startups, believe extraordinary expectations produce extraordinary outcomes, and want to invest your energy into developing the next generation of entrepreneurs, we'd love to meet you.

What you will be doing

  • Coach and motivate a cohort of student founders through weekly 1:1s, daily check-ins, and group stand-ups that keep them making measurable progress.
  • Hold an exceptionally high bar for execution while providing the support and accountability students need to overcome obstacles and keep building.
  • Monitor student progress through FounderOS, identify when students are stuck, and connect them with mentors, Entrepreneurs-in-Residence, or other resources that accelerate their growth.
  • Help build the culture, traditions, workshops, events, and day-to-day operating rhythm of a world-class entrepreneurial high school.
  • Travel with students several times each year while building lasting relationships with founders, investors, operators, and entrepreneurial families.

What you will NOT be doing

  • Acting as the primary startup consultant or developing business strategy for students. FounderOS, Entrepreneurs-in-Residence, and visiting mentors own that work.
  • Teaching traditional academic classes or grading coursework.
  • Accepting average effort from students capable of exceptional performance.
  • Running workshops outside your area of expertise or relying on generic startup advice.
  • Working inside a rigid school system where bureaucracy gets in the way of meaningful student outcomes.

Key responsibilities

Create an environment where every student consistently grows as an entrepreneur by combining exceptional coaching, high accountability, meaningful connections, and a culture that turns ambitious teenagers into capable founders.

Candidate requirements

  • At least 3 years of leadership or high-impact experience within a startup or high-growth business.
  • Strong business judgment and the ability to confidently engage with early-stage founders while knowing when to involve subject matter experts.
  • Demonstrated ability to coach, motivate, and hold high-performing individuals accountable.
  • Daily, hands-on experience using AI to improve the quality and speed of your work.
  • Outstanding communication and relationship-building skills with students, families, mentors, and founders.
  • Willingness to work full-time on-site in New York City, with occasional travel throughout the year.
  • 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 established network of founders, investors, operators, or mentors.
  • Experience in early-stage startups where you regularly operated across multiple functions.

Meet a successful candidate

Watch Interview
Chris Hayes
Chris  |  L2 Guide
United States

Ever wondered if work is enhancing your life, or erasing it? After years of late nights as a fitness coach left him exhausted and disconnect...

Meet Chris

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.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

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

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

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.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.