Demo

Personalized Learning Guide K-2, Alpha - $120,000/year USD

Crossover
Greenwich, CT Full Time
POSTED ON 4/17/2026
AVAILABLE BEFORE 7/6/2026
  • Located on-site at an Alpha School campus (Chicago, IL
  • Miami, FL
  • Palo Alto, CA
  • Piedmont, CA
  • San Francisco, CA
  • Santa Monica, CA
  • Lake Forest, CA
  • Greenwich, CT
  • Boston, MA; relocation assistance available)
  • $120,000 annually, paid weekly. Health, dental, and vision benefits begin day one
  • School-year calendar with defined working hours

The kindest thing you can do for a 6-year-old who achieved 99% is not round it up to 100%. If that principle feels uncomfortable, this position is not for you. If it feels self-evident, if you believe children meet the expectations you set for them, this role is designed for you.

Alpha operates differently from conventional schools. Students progress through academics via adaptive software that identifies their current level and advances at their individual pace. There are no classroom lectures. No identical worksheets distributed to 25 students. Instead, each child engages with personalized learning applications while you, their Guide, support them through challenges: maintaining focus when difficulty increases, working through frustration, and recognizing genuine mastery rather than mere participation.

Your day begins with motivation sessions: analyzing each student's performance in their learning applications, establishing daily objectives, and identifying the appropriate motivator for each child. This might be a leaderboard competition, school currency system, or a direct conversation about their potential. Afternoons transition to life skills workshops where you facilitate instruction in public speaking, focus, and feedback skills through hands-on, project-driven activities. You'll administer mastery-based assessments (Test2Pass) where students demonstrate they have truly learned the skill, not simply attended the lesson. Throughout, you're developing emotional regulation, resilience, and problem-solving abilities through consistent structure combined with warmth.

The Guides who excel in this role advance to Lead Guide positions, mentoring teams of Guides while maintaining direct work with their own cohort. The progression from "I transformed these 15 children's lives" to "I'm developing the team that transforms hundreds" is tangible and achievable. If traditional education has never appealed to you but you understand that what occurs between ages 4 and 7 determines everything that comes after — apply.

What You Will Be Doing

  • Facilitating daily motivation sessions with K-2 students: analyzing Coachbot analytics, establishing individualized objectives, and applying Alpha's motivational framework (school currency, leaderboards, 1-on-1 coaching) to achieve 100% goal completion
  • Leading one-hour life skills workshops focused on public speaking, concentration, giving/receiving feedback, and time management, all hands-on and project-based, aligned with Alpha's curriculum playbook
  • Developing emotional regulation, resilience, and problem-solving skills in partnership with Reading Specialists who manage literacy instruction
  • Conducting Test2Pass mastery assessments where students prove they have internalized each life skill before progression
  • Establishing authentic relationships with each student by understanding their interests, capabilities, and challenges so your coaching remains personal rather than generic

What You Won’t Be Doing

  • Delivering lectures from the front of the classroom or providing academic instruction. Students learn academics through adaptive apps, not from you.
  • Creating curriculum independently. Alpha supplies the life skills curriculum and lesson plans; your role is to execute them effectively.
  • Advancing students who have not demonstrated mastery. If they achieved 99%, you coach them to 100%.
  • Supervising children on computers passively. Every moment is organized around active coaching, motivation, and skill development.
  • Handling parent communications or campus-wide operations. Those responsibilities belong to the Campus Lead.

Personalized Learning Guide K-2 Key Responsibilities

Coach a cohort of K-2 students who thrive at school, progress through adaptive learning at twice the conventional pace, and develop essential life skills.

Basic Requirements

  • Bachelor's degree in any field
  • Minimum 3 years of experience working with children ages 4–7 (education, afterschool programs, coaching, camps, or similar)
  • Experience leading groups of young children with both structure and high engagement
  • Engaging storyteller and dynamic speaker capable of holding the attention of a room full of 5-year-olds
  • Demonstrates continuous improvement based on feedback
  • Willing to work in-person at an Alpha campus (Chicago, IL
  • Miami, FL
  • Palo Alto, CA
  • Piedmont, CA
  • San Francisco, CA
  • Santa Monica, CA
  • Lake Forest, CA
  • Greenwich, CT
  • Boston, MA; relocation support available)
  • Legally authorized to work in the US without sponsorship

Nice-to-have Requirements

  • Background in youth athletics coaching, summer camp leadership, or afterschool program coordination where you managed both engagement and outcomes
  • Performance experience (theater, public speaking, improv) that enables you to command a room of young children
  • Experience with adaptive learning platforms or ed-tech tools in a classroom or tutoring environment
  • Track record as a high performer yourself, academically, athletically, or professionally, that informs your approach to holding children to the same standard

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 $60 USD/hour, which equates to $120,000 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-5634-US-Greenwic-PersonalizedLe

Salary : $120,000

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