Startup 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 

Not accepting applications on crossover.com at this time.

Description

  • On-site in Austin, TX (relocation assistance available)
  • $150,000 annually, paid each week. Health benefits begin day one.

The most meaningful support you can offer a teenager launching a business is to refuse to let them settle for less. You believe that setting high standards isn't applying pressure—it's demonstrating your confidence in their ability to reach those standards. If that perspective resonates with you, continue reading.

You'll work with high school students who are launching real companies with $1M revenue potential. These aren't classroom exercises or mock scenarios. Approximately 60-65% of your time will be dedicated to 1:1 coaching: pinpointing where each founder encounters obstacles, determining the most impactful next step, and ensuring accountability to a defined action plan. The remaining 35-40% divides between overseeing academic performance and facilitating workshops designed to deliver practical, actionable skills rather than theoretical content.

This isn't a traditional teaching position. You're accountable for the full picture of student success: venture advancement, academic performance, and personal development simultaneously. You'll rely on dashboards, business progress reports, and academic metrics to coach with clarity and precision, not guesswork. When a student's grades begin to decline, you step in proactively. When a venture hits a plateau, you surface the actual issue, not the easier conversation.

Your first step is understanding each student's business, identifying their natural strengths, and recognizing their sticking points. Within a few months, you become the voice they trust when challenged—because you've built businesses yourself. The payoff is seeing a 16-year-old arrive with an idea and leave with a working company, the habits to sustain it, and academic results that preserve every future opportunity.

If you've been searching for a role where your operational background directly influences the next wave of entrepreneurs, apply now. If you prefer structured lesson plans, predictable classroom environments, or roles where effort alone is celebrated, this isn't the right fit.

What you will be doing

  • Providing 1:1 coaching to student founders on strategy, execution, and scaling decisions — approximately two-thirds of your time
  • Leveraging dashboards, venture updates, and academic metrics to assess progress and identify priority actions
  • Tracking academic results and stepping in early when attention or time management begins to falter
  • Designing and running workshops that deliver clear, applied outcomes
  • Facilitating stand-ups, debriefs, and team discussions that reinforce accountability to personal commitments

What you will NOT be doing

  • Teaching traditional lessons or adhering to a prescribed syllabus (you guide experiential learning, not classroom lectures)
  • Offering general advice or inspirational messaging without concrete follow-up actions
  • Handling administrative tasks — calendar coordination, forms, or admissions processes
  • Attending lengthy staff meetings or managing institutional red tape (your focus remains on direct student impact)

Key responsibilities

Guide student founders toward building ventures with $1M revenue potential while ensuring their academic performance remains strong.

Candidate requirements

  • Must be willing to work on-site at Alpha High School in Austin, TX (relocation assistance provided)
  • Minimum of 2 years coaching or developing others (whether direct reports, peers, or clients), with a concrete example of a coaching engagement and measurable results
  • Professional background owning critical outcomes or performance metrics, including at least one example showing $500,000+ in annual revenue impact
  • At least 1 year working directly with young people (students, early-career professionals, or participants in youth initiatives) on projects, skill development, or entrepreneurial ventures
  • Legal authorization to work in the United States

Nice to have

  • Experience founding, co-founding, or running a startup or early-stage venture
  • Background as a Chief of Staff, program manager, or top-tier individual contributor with end-to-end ownership of outcomes
  • Familiarity with AI tools (such as ChatGPT, Copilot) to enhance coaching preparation, analysis, or messaging
  • Experience in K-12 education, EdTech, or programs combining academics with hands-on application (such as accelerators, project-based curricula, or entrepreneurship initiatives)

Meet a successful candidate

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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...

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Chat-style
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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
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STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

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