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Personalized Learning Guide K-2, Alpha

Job in Stamford, Fairfield County, Connecticut, 06925, USA
Listing for: Crossover
Full Time position
Listed on 2026-10-06
Job specializations:
  • Education / Teaching
    Youth Development, Career & Life Skills Coaching
Salary/Wage Range or Industry Benchmark: 120000 USD Yearly USD 120000.00 YEAR
Job Description & How to Apply Below
Position: Personalized Learning Guide K-2, Alpha - $120,000/year USD
  • On-site role at an Alpha School campus (Chicago, IL
  • Miami, FL
  • Piedmont, CA
  • Santa Monica, CA
  • Lake Forest, CA
  • Boston, MA; relocation assistance available)
  • Annual compensation of $120,000, distributed weekly. Full health, dental, and vision coverage begins on day one
  • Aligned with the school-year calendar and predictable daily hours
  • On-site role 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)
  • Annual compensation of $120,000, distributed weekly. Full health, dental, and vision coverage begins on day one
  • Aligned with the school-year calendar and predictable daily hours

The kindest thing you can do for a 6-year-old who achieves 99% is to withhold calling it 100%. If that principle feels uncomfortable, this role isn't for you. If it resonates, if you believe children meet the expectations you set for them, this position was designed with you in mind.

Alpha operates differently from conventional schools. Academic learning happens through adaptive software that adjusts to each student's current level and progresses at their individual pace. There are no teacher-led lessons. No identical worksheets distributed to 25 students assumed to be at the same point. Instead, each child advances through personalized learning applications while you—their Guide—support them through the challenging moments: maintaining focus when the content becomes difficult, working through frustration, and recognizing true mastery rather than mere effort.

Your day begins with motivational sessions: analyzing each student's performance in their learning applications, establishing daily objectives, and identifying the right motivational approach for each child. For some, that might be a leader board competition, school‐based currency, or a one‑on‑one discussion about their potential. The afternoon transitions to life skills workshops where you facilitate instruction in public speaking, concentration, and constructive feedback through project‑based, interactive activities.

You'll conduct mastery‑based evaluations (Test2

Pass) where students must prove they've truly absorbed the skill, not simply attended the session. Throughout, you're guiding emotional self‑regulation, building resilience, and teaching problem‑solving through consistent expectations and supportive presence.

Guides who excel in this role advance to Lead Guide positions, mentoring teams of Guides while continuing direct work with their own student cohort. The progression from "I transformed these 15 children's trajectories" to "I'm developing the team that impacts hundreds" is concrete and achievable. If traditional education never appealed to you but you understand that what occurs between ages 4 and 7 establishes the foundation for everything afterward—submit your application.

What You Will Be Doing
  • Conducting daily motivational sessions with K-2 students: analyzing Coachbot data, establishing personalized objectives, and applying Alpha's motivational framework (school currency, leaderboards, individual coaching) to achieve 100% goal attainment
  • Facilitating one‑hour life skills workshops focused on public speaking, concentration, constructive feedback exchange, and time management—all experiential and project‑driven, adhering to Alpha's curriculum framework
  • Guiding emotional self‑regulation, resilience, and critical thinking in collaboration with Reading Specialists responsible for literacy development
  • Overseeing Test2

    Pass mastery evaluations where students prove comprehension and internalization of each life skill prior to progression
  • Establishing authentic connections with every student by understanding their passions, capabilities, and…
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