Preschool Head Teacher, Alpha - $120,000/year USD

Alpha School; Chicago (IL); On-site; USD 89,000 - 121,000; Full time

Job summary

Alpha School in Chicago, IL is seeking a Head Teacher for a full-time Pre-K classroom on-site. You will design play-based experiences that foster early literacy, numeracy, emotional safety, and social development while tracking measurable progress.

Join a mission-driven team that treats preschool as foundational learning, with relocation assistance offered for NYC and Chicago openings. This role offers competitive compensation and benefits.

Qualifications

• Able to work full-time, on-site at Manhattan, New York, or Chicago, Illinois (relocation assistance is available)
• An associate's degree or higher, or any U.S. state teaching license or certification
• At least 2 years of experience working with children ages 3-5 in a structured, play-based classroom or group setting
• Experience documenting developmental milestones using a structured framework or assessment tool (Teaching Strategies GOLD, ASQ, HighScope COR, etc.)
• Authorized to work in the U.S. without sponsorship
• For the Chicago opening, a Montessori certificate or experience as a Reading Specialist

Responsibilities

• Design joyful, sensory-rich learning experiences that intentionally build early literacy, numeracy, self-regulation, and social development.
• Create a classroom where every child feels emotionally safe, deeply known, and excited to come to school every day.
• Observe children's development in real time, document meaningful progress, and use those insights to personalize learning.
• Adjust activities around each child's interests and developmental needs, helping every learner make measurable progress.
• Partner closely with families to share growth, celebrate milestones, and support each child's development beyond the classroom.

Skills

Play-based learning

Child development observation

Family partnership

Education

Associate's degree or higher, or teaching license

Tools

Teaching Strategies GOLD

ASQ

HighScope COR

Job description

"I got my time back, and I still get to be passionate and work with students."

— Christie, former school principal, now Alpha Reading Specialist

Alpha is hiring.

You already know the difference between childcare and real early education. You've seen what happens when a preschool classroom is treated as a profession rather than a holding pattern before kindergarten—and you've probably also seen what happens when it isn't.

If you're the kind of Head Teacher who believes play is serious work, relationships come before academics, and every interaction is an opportunity for growth, you'll feel at home at Alpha.

This is a full‑time, on‑site role leading a Pre‑K classroom where emotional safety, curiosity, and measurable developmental growth are equally important. You'll design rich, play‑based experiences that help children build confidence, resilience, early literacy, numeracy, and a genuine love of learning. We hire educators who know great preschool isn't childcare—it's the foundation for everything that comes next.

Alpha is reimagining education by helping students master academics faster, creating more time to develop the life skills that matter just as much. That vision begins in Pre‑K with exceptional teachers who know how to turn play into purposeful learning.

We're currently hiring in Manhattan, New York City and in Chicago, Illinois. We expect to hire from across each metro area, and if you're an outstanding educator who wants to move closer to either city, we'll provide relocation assistance.

What You Will Be Doing

• Design joyful, sensory‑rich learning experiences that intentionally build early literacy, numeracy, self‑regulation, and social development.
• Create a classroom where every child feels emotionally safe, deeply known, and excited to come to school every day.
• Observe children's development in real time, document meaningful progress, and use those insights to personalize learning.
• Adjust activities around each child's interests and developmental needs, helping every learner make measurable progress.
• Partner closely with families to share growth, celebrate milestones, and support each child's development beyond the classroom.

What You Won’t Be Doing

• Supervising children without a clear developmental purpose behind every activity.
• Following scripted lessons, relying on worksheets, or teaching to compliance instead of curiosity.
• Spending your day managing behavior rather than helping children develop emotional regulation.
• Sitting children in front of academic software while you monitor from the sidelines.

Preschool Head Teacher Key Responsibilities

Create a Pre‑K classroom where every child develops a lasting love of learning while making exceptional progress across the developmental foundations that shape lifelong success.

Basic Requirements

• Able to work full‑time, on‑site at one of our campuses: Manhattan, New York, or Chicago, Illinois (relocation assistance is available)
• An associate's degree or higher, or any U.S. state teaching license or certification
• At least 2 years of experience working with children ages 3‑5 in a structured, play‑based classroom or group setting
• Experience documenting developmental milestones using a structured framework or assessment tool (Teaching Strategies GOLD, ASQ, HighScope COR, etc.)
• Authorized to work in the U.S. without sponsorship
• For the Chicago opening, a Montessori certificate or experience as a Reading Specialist

Nice-to-have Requirements

• Experience in a Reggio Emilia, Montessori, Bank Street, or other inquiry‑based early childhood program
• Experience in an independent school or an academically ambitious preschool
• Familiarity with child‑development frameworks, observation tools, or portfolio‑based assessment
• Experience adapting play‑based activities to individual interests, needs, and developmental goals

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.

There is so much to cover for this exciting role, and space here is limited.

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 $120,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.