Demo

Leadership and Growth Coach, Alpha - $150,000/year USD

Crossover
Chicago, IL Full Time
POSTED ON 5/5/2026
AVAILABLE BEFORE 7/27/2026
  • On-site at Alpha School campuses in Santa Barbara, CA; Santa Monica, CA; San Francisco, CA; Greenwich, CT; Boston, MA; or New York City, NY
  • $150,000/year W2 salary, paid weekly. Day-one health benefits.
  • Relocation support for a one-school-year campus commitment

You believe that refusing to lower the bar is the most meaningful thing you can do for a student. You've reached levels of performance in competition, building, or achievement that most people only observe from a distance: elite-level athletics, a top-tier university with honors, a highly selective organization, or a venture you launched and grew yourself. Now imagine channeling that intensity into a room of K-12 students who have never encountered someone with your caliber of experience, someone willing to hold them to standards they didn't believe they could meet. If the idea of holding students to elite expectations feels too demanding, this role isn't for you.

Alpha leverages AI-powered 1-on-1 learning that allows students to complete core academics in roughly two hours per day. This design frees the remainder of the day for life skills, passion projects, and meaningful development. At Alpha's most rigorous campuses, students require more than oversight. They need a credible mentor whose personal accomplishments establish the benchmark: someone capable of reading the room, shaping the environment, and coaching through resistance, distractions, and doubt.

Your role is not instructional. AI manages the academic content. Your responsibility is to motivate, coach, and hold students to the same rigorous standard you've applied to yourself. Forty percent of your time is spent in direct 1-on-1 and small-group coaching that identifies obstacles and establishes ambitious targets. Another forty percent involves leading structured life-skills workshops designed for mastery, not engagement alone. The final twenty percent is devoted to morning kickoffs that set a daily tone where mediocrity has no place.

The trajectory here emphasizes depth over advancement. You begin by mastering Alpha's approach and earning student trust. Within months, you become the person students trust enough to push them beyond their perceived limits. The reward is not a title change. It's the same students, year after year, maturing with you as their consistent advocate. It's witnessing a student who avoided eye contact in September deliver a confident presentation to a roomful of adults in May.

This role remains student-facing. Students are the purpose, not a platform for career advancement. If your motivation to leave your current role is mission-driven rather than resume-driven, apply now.

What You Will Be Doing

  • Conducting 1-on-1 and small-group coaching sessions using Coachbot analytics and student performance data to identify obstacles, establish ambitious objectives, and enforce accountability for execution
  • Leading structured life-skills workshops designed for mastery, drawing on credible storytelling from your own elite background, and evaluating mastery through Alpha's Test2Pass system
  • Establishing the cultural standard each morning through focused kickoffs that reinforce high-performance norms across the campus
  • Monitoring student progress in real time and adapting coaching approaches based on data rather than intuition
  • Cultivating trusted mentor relationships with students and families through high expectations, consistency, and documented motivation strategies

What You Won’t Be Doing

  • Teaching lessons, creating curriculum, or grading assignments — Alpha's AI-powered academic system manages instruction; you manage motivation
  • Lecturing to a classroom of 30 students (your focus is high-touch coaching in small groups, not broadcast instruction)
  • Supervising other staff or advancing through an administrative hierarchy (this role centers on direct student impact, not organizational structure)
  • Attending faculty meetings or navigating institutional bureaucracy (your time remains dedicated to students)
  • Lowering standards to satisfy metrics (if a student achieves 99%, your task is to identify what prevented 100%)

Leadership And Growth Coach Key Responsibilities

Drive exceptional student motivation, growth, and life-skill mastery at Alpha's highest-expectation campuses.

Basic Requirements

  • Bachelor's degree
  • At least one instance of exceptional achievement in a highly selective, globally recognized domain (examples: national or international competition medals, top-tier university with distinction, highly selective firm or fellowship, elite performing arts institution, or founding and scaling a successful venture)
  • At least 3 years of experience in student coaching, youth mentoring, athletic coaching, or leadership roles where you measurably raised others' performance
  • Willing to work in-person at an Alpha campus in Santa Barbara, CA; Santa Monica, CA; San Francisco, CA; Greenwich, CT; Boston, MA; or New York City, NY (relocation support provided)
  • Legal right to work in the United States

Nice-to-have Requirements

  • Background in elite competitive athletics (varsity D1, national team, or professional level) with experience coaching or mentoring younger athletes
  • Experience in high-accountability environments like management consulting, investment banking, or military leadership
  • Track record of youth development through mentoring in non-academic settings (community organizations, after-school programs, sports camps)
  • Comfort presenting to and building trust with high-expectation families paying premium private school tuition

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-5740-US-Chicago-LeadershipandG.008

Salary : $150,000

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