Entrepreneurship Coach, Alpha - $150,000/year USD

• On-site position in Austin, TX (relocation assistance available)
• $150,000 annual salary, paid weekly. Health benefits start day one.
  
  

The best way to support a teenage founder is to refuse mediocrity. You understand that high expectations aren't burdensome—they signal belief in what the student is capable of achieving. If this resonates with you, continue reading.

You'll work with high school students building genuine companies with $1M upside. These aren't classroom exercises or hypothetical scenarios. Approximately 60-65% of your time goes to 1:1 coaching: pinpointing where founders are blocked, isolating the highest-impact next step, and enforcing accountability to a concrete action plan. The remaining 35-40% divides between academic monitoring and facilitating workshops designed to build practical skills, not just deliver content.

This role is not about teaching. You are accountable for student outcomes across three dimensions: venture traction, academic performance, and personal development. You'll rely on dashboards, progress reports, and academic metrics to coach with data-driven clarity, not gut feeling. When a student's grades decline, you step in before it escalates. When a venture loses momentum, you surface the actual issue, not the one that's easiest to discuss.

You begin by understanding each student's business, their capabilities, and their friction points. Over time, you become the voice they trust to challenge them—because you've operated in similar environments yourself. The payoff is seeing a 16-year-old arrive with an idea and leave with a live business, the systems to sustain it, and academic results that preserve future optionality.

If you're seeking a position where your operational background directly influences emerging founders, apply now. If you prefer structured lesson plans, classroom predictability, or environments where effort alone is rewarded, this isn't the right fit.

What You Will Be Doing

• Providing 1:1 coaching to student founders on strategy, execution, and scaling—consuming roughly two-thirds of your weekly schedule
• Leveraging student dashboards, venture updates, and academic metrics to assess progress and clarify immediate priorities
• Tracking academic performance and stepping in proactively when time management or focus begins to waver
• Designing and running workshops that deliver tangible, applied-learning outcomes
• Facilitating stand-ups, retrospectives, and group sessions that reinforce student accountability to their stated objectives
  
  

What You Won’t Be Doing

• Teaching lectures or adhering to a predetermined curriculum (you enable hands-on learning, not traditional instruction)
• Offering broad mentorship or motivational guidance without clear action-item follow-up
• Handling student administration—scheduling, documentation, or enrollment processes
• Attending faculty meetings or navigating institutional bureaucracy (your focus remains with students)
  
  

Entrepreneurship Coach Key Responsibilities

Advance student founders toward ventures with $1M potential while maintaining their academic trajectory.

Basic Requirements

• Willing to work on-site at Alpha High School in Austin, TX (relocation assistance provided)
• At least 2 years coaching or developing others (direct reports, peers, or clients), including a concrete example of a coaching engagement and its measurable outcomes
• Professional experience holding accountability for critical outcomes or metrics, with at least one example reflecting $500,000 in annual revenue impact
• At least 1 year working with young people (students, early-career professionals, or youth program participants) on projects, learning objectives, or ventures
• Legally authorized to work in the United States
  
  

Nice-to-have Requirements

• Founded, co-founded, or held an operating role in a startup or early-stage company
• Experience as a Chief of Staff, program leader, or high-impact individual contributor with full ownership of outcomes
• Proficiency with AI tools (e.g., ChatGPT, Copilot) to enhance coaching preparation, analysis, or communication workflows
• Background in K-12 education, EdTech, or programs integrating academics with real-world execution (accelerators, project-based learning, entrepreneurship initiatives)
  
  

About Alpha

Want to join a learning rebellion that’s transforming the traditional classroom?

Alpha School is on a mission to reshape education with a bold approach that harnesses AI to accelerate learning and unleash student potential.

They don’t play by the old rules.

Alpha is creating a new paradigm where students master core academics in just two hours a day, freeing up time for hands-on, passion-driven learning that truly prepares them for the real world.

Alpha School is rewriting the rules of education.

Sounds too good to be true? It’s not.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $75 USD/hour, which equates to $150,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5757-US-Philadel-Entrepreneursh.001