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

Crossover; Austin (TX); On-site; USD 140,000 - 160,000; Full time

Benefits offered by this job

Relocation support

Job summary

Alpha High School in Austin, TX seeks an Entrepreneurship Coach to guide teen founders toward real ventures while maintaining academic progress. You will diagnose progress using dashboards and updates, intervene early to keep focus, and lead workshops that turn learning into action.

You will own student outcomes—venture progress, academics, and personal growth—while mentoring through structured action plans and outcomes-based coaching.

Qualifications

• Minimum 2 years coaching or developing others with a specific example of a coaching relationship and its outcomes.
• Experience owning outcomes or metrics with at least one example demonstrating $500,000+ annual revenue impact.
• At least 1 year working with young people on projects, learning goals, or ventures.
• Legally authorized to work in the United States.

Responsibilities

• Coaching student founders 1:1 through strategy, execution, and growth decisions.
• Using dashboards, business updates, and academic data to diagnose progress and define actions.
• Monitoring academic performance and intervening early when focus or time management slips.
• Preparing and facilitating workshops with clear applied-learning takeaways.
• Leading stand-ups, debriefs, and group discussions to keep students accountable.

Skills

Coaching

Outcomes ownership

Data-driven

Tools

AI tools (ChatGPT)

Job description

"Alpha School students, on average, experience 2.4 to 2.6 times the academic growth of traditional school students" — Forbes

Alpha is hiring.

The most supportive thing you can do for a teenager building a company is refuse to let them settle. You believe high standards are not pressure, they're proof you think the student can actually get there. If that feels obvious to you, keep reading.

Your students are high schoolers building real companies with $1M potential. Not class projects. Not simulations. You'll spend 60-65% of your time in 1:1 coaching sessions: diagnosing where each founder is stuck, identifying the highest-leverage move, and holding them to a clear action plan. The other 35-40% splits between academic oversight and leading workshops that leave students with applied skills, not just notes.

This is not a teaching job. You own student outcomes: venture progress, academic standing, and personal growth at the same time. You'll use dashboards, business updates, and academic data to coach with precision, not intuition. A student's academics slip? You intervene before it becomes a crisis. A venture stalls? You name the real problem, not the comfortable one.

You start by learning each student's venture, their strengths, and where they stall. Within months, you're the person whose push they actually trust, because you've been in the arena yourself. The reward is watching a 16-year-old who came in with an idea leave with a functioning business, the discipline to run it, and grades that keep every door open.

What You Will Be Doing

• Coaching student founders 1:1 through strategy, execution, and growth decisions — roughly two-thirds of your week
• Using student dashboards, business updates, and academic data to diagnose progress and define next actions
• Monitoring academic performance and intervening early when focus or time management slips
• Preparing and facilitating workshops with clear applied-learning takeaways
• Leading stand-ups, debriefs, and group discussions that keep students accountable to their own goals

What You Won’t Be Doing

• Lectures and pre-set curricula have no place here — you facilitate applied learning, not classroom instruction
• Providing general mentorship or motivational talks without follow-through on action items
• Managing student administration — scheduling, paperwork, or enrollment logistics
• Sitting through faculty meetings or navigating school bureaucracy (your time stays focused on students)

Entrepreneurship Coach Key Responsibilities

Drive student founders toward $1M-potential ventures while keeping them on track academically.

Basic Requirements

• Willing to work on-site at Alpha High School in Austin, TX (relocation support provided)
• At least 2 years coaching or developing others (direct reports, peers, or clients) with a specific example of a coaching relationship and its outcomes
• Professional experience owning key outcomes or metrics, with at least one example demonstrating $500,000+ annual revenue impact
• At least 1 year working with young people (students, early-career professionals, or youth program participants) on projects, learning goals, or ventures
• Legally authorized to work in the United States

Nice-to-have Requirements

• Founded, co-founded, or operated a startup or early-stage business yourself
• Experience as a Chief of Staff, program lead, or high-performing individual contributor where you owned outcomes end-to-end
• Comfort using AI tools (e.g., ChatGPT, Copilot) to support coaching prep, analysis, or communication
• Background in K-12 education, EdTech, or programs that blend academics with real-world application (accelerators, project-based learning, entrepreneurship programs)

About Alpha

Join the team building school around student growth

Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills.

Roles with real student impact: Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members.

Education work that pays like it matters: Alpha offers six-figure roles for people ready to help build a radically better school experience.

A culture built for builders: Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it.

Alpha is where you can do the most meaningful work of your career.

Working with us

This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year-long positions. The compensation level for this role is $150,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.