Entrepreneurship Coach
$150,000 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; Orange County (Lake Forest), CA; San Francisco, CA; or Santa Barbara, CA
In-person
8-5, M-F
full-time (40 hrs/week)
Long-term role

Entrepreneurship Coach   $150,000 USD/year

Description

  • On-site at Alpha School locations: New York City, NY · Orange County (Lake Forest), CA · San Francisco, CA · Santa Barbara, CA
  • $150,000 annual compensation, distributed weekly. Full health coverage begins day one.
  • Relocation assistance provided

You have reached the upper echelon of a demanding, competitive arena. Perhaps through elite-level sports, a distinguished record at a top university, a role at a highly selective organization, or a venture you launched and grew yourself. You understand what separates participation from genuine competition. Consider applying that discipline in a setting where K-12 students gain access to a mentor of your caliber—someone who will hold them to standards they have not yet imagined for themselves.

Alpha employs AI-driven 1:1 instruction that enables students to complete core academics in roughly two hours daily. The remainder of their schedule is dedicated to life skills, interest-based projects, and substantive personal development. At Alpha's most rigorous campuses, students require more than oversight. They need a credible mentor whose personal track record establishes the benchmark: an individual capable of managing group dynamics, defining expectations, and guiding students through resistance, distraction, and doubt.

This position does not involve traditional teaching; it centers on coaching, challenging, and maintaining the same exacting standards you have applied to your own work. Eighty percent of your time will be devoted to direct one-on-one sessions, small-group coaching, and life-skills instruction. The remaining twenty percent involves establishing daily momentum through focused openings that build a culture where mediocrity is not tolerated.

Advancement in this role is not about moving into management. It is about deepening impact. You begin by mastering Alpha's methodology and earning student trust. Within months, you become the mentor students rely on to push them beyond self-imposed limits. The reward is not a title change. It is observing a student who avoided eye contact in September deliver a confident presentation to adults in May.

If your elite background has left you seeking work that carries meaning beyond personal achievement, this is your opportunity. If you prefer structured lesson plans, conventional classroom routines, or a path toward administrative roles, this position is not the right fit.

What you will be doing

  • Conducting one-on-one and small-group coaching that identifies individual obstacles, establishes challenging objectives, and enforces accountability for execution
  • Leading structured life-skills instruction designed for skill mastery rather than engagement, drawing on credible examples from your own high-performance background
  • Evaluating student progress using platforms such as Test2Pass and monitoring performance through Coachbot analytics to refine coaching approaches dynamically
  • Establishing campus culture each morning via focused opening sessions that communicate and reinforce high-performance standards
  • Developing trusted mentorship with students and their families by maintaining high expectations, consistency, and documented motivation strategies

What you will NOT be doing

  • Developing lesson plans, creating curricula, or evaluating assignments. Alpha's academic infrastructure manages these functions independently.
  • Teaching large groups of 30 students. Your focus is intensive coaching in small settings, not large-format instruction.
  • Supervising other personnel or pursuing administrative advancement. This role emphasizes direct student outcomes, not organizational management.
  • Attending faculty meetings or working through institutional procedures. Your schedule remains concentrated on student interaction.
  • Compromising standards to meet targets. If a student achieves 99%, your responsibility is to identify what prevented them from reaching 100%.

Key responsibilities

Lead outstanding student motivation, development, and life-skill acquisition at Alpha's most demanding campuses.

Candidate requirements

  • Bachelor's degree
  • At least one documented instance of exceptional performance in a highly selective, internationally recognized field (examples include: medals in national or international competitions, distinguished academic record at a top-tier university, position at a highly selective organization or fellowship, training at an elite performing arts institution, or founding and growing a successful enterprise)
  • Minimum of 3 years in student coaching, youth mentorship, athletic coaching, or leadership positions where you demonstrably elevated others' performance
  • Availability to work on-site at an Alpha campus in New York City, NY; Orange County (Lake Forest), CA; San Francisco, CA; or Santa Barbara, CA
  • Authorization to work legally in the United States

Nice to have

  • History in elite competitive sports (Division 1 varsity, national team representation, or professional level) with coaching or mentoring experience for younger athletes
  • Professional experience in high-accountability fields such as management consulting, investment banking, or military leadership
  • Demonstrated youth development through mentoring outside traditional academic contexts (community groups, after-school initiatives, sports camps)
  • Ability to present effectively to and establish rapport with high-expectation families investing in premium private education

Meet a successful candidate

Watch Interview
CeCe
CeCe  |  Lead Guide
United States

Has the harsh reality of teaching in a broken system worn you down? This compassionate Lead Guide is redefining what it means to support kid...

Meet CeCe

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

School sucks. So we’re fixing it.

The education Olympics

The education Olympics

It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game. 

Salary without side gigs

Salary without side gigs

Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.

Skills make the grade

Skills make the grade

Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join America’s largest community of  AI first education leadersAI-first education leaders.