The Best Ed Tech Jobs in Chicago, US

Are your big ideas too cool for school? Join Crossover to qualify for the world's most innovative (and well-paid) jobs in education technology.

  • Work full-time for leading US schools and EdTech companies, joining a hybrid team of on-campus guides and global remote experts.
  • No teaching experience or lesson planning required. Your job: inspire young people to achieve their potential.
  • Develop next-gen AI education software with the limitless resources of well-funded US startups.
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Earn up to

$400,000 USD/Year


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The Best Ed Tech Jobs in Chicago, US
Earn up to $400,000 USD/YEAR

Apply Now

Role Description

Looking for groundbreaking roles that fuse your love for technology and education? Then you’re looking for our highly paid jobs in EdTech.

But you won’t find traditional teaching jobs here - because we don’t do ‘business as usual’ in our educational roles.

At Crossover, we hunt for extraordinary educators, technologists, and industry professionals ready to shake up Ed Tech. Then we match the smartest people in the world with the best jobs in education technology in the US.

The only must-have is an unrelenting passion for transforming education.

Many of our hires are former teachers eager to make an impact beyond the classroom, but we welcome top talent from all walks of life - as long as you can prove you’ve got the skills to back it up.

We partner with top-tier EdTech companies and elite institutions like Alpha School, 2 Hour Learning, and Texas Sports Academy - offering high-impact roles on campus in the US and remotely worldwide.

  • Earn 1.5x to 3.8x more than your current pay
  • No grading, bureaucracy, or unpaid overtime
  • Clear career progression & leadership opportunities
  • Better work-life balance - without the classroom chaos
  • Join an elite team of top education pros who are valued & respected

Whether you're an instructional designer, curriculum developer, education consultant, or an AI-driven learning innovator, our jobs put you at the forefront of technology-driven education.

If you want to lead at the intersection of AI, technology, motivation, and education, you’re exactly where you need to be.

Welcome to the best jobs in EdTech on Crossover.

Featured education jobs in US

What's your dream job?

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CALIFORNIA, US

Associate Dean of Parents - Bay Area

$250,000 USD/year
SCOTTSDALE, AZ, US

Admissions Associate - Scottsdale

$75,000 USD/year
AUSTIN, TX, US

High School Elite Guide

$150,000 USD/year
SPRINGFIELD, MA, US

Guide - Springfield

$100,000 USD/year
UNITED STATES

Lead Guide II K-3

$200,000 USD/year
CALIFORNIA, US

Director of Admissions - Bay Area

$250,000 USD/year
CALIFORNIA, US

Associate Dean of Parents - CA

$200,000 USD/year
HOUSTON, TX, US

Guide - Houston

$100,000 USD/year
AUSTIN, TX, US

High School Elite Guide - Entrepreneurship

$150,000 USD/year
CALIFORNIA, US

Admissions Associate - San Francisco

$100,000 USD/year
NY, US

PreK Guide II

$120,000 USD/year
UNITED STATES

Elite Guide

$150,000 USD/year
AUSTIN, TX, US

PreK Lead Guide

$150,000 USD/year
SPRINGFIELD, MA, US

Campus Director

$200,000 USD/year
UNITED STATES

Campus Operations Coordinator

$110,000 USD/year
UNITED STATES

Guide II K-3

$120,000 USD/year
UNITED STATES

Reading Specialist II

$120,000 USD/year
UNITED STATES

Campus Logistics Coordinator

$90,000 USD/year
UNITED STATES

Lead Guide II

$200,000 USD/year
UNITED STATES

Campus Coordinator

$75,000 USD/year
UNITED STATES

Guide II

$120,000 USD/year
UNITED STATES

Associate Dean of Parents

$200,000 USD/year
UNITED STATES

Director of Admissions

$200,000 USD/year
MULTIPLE LOCATIONS

Guide Assistant

$30 USD/hour
BROWNSVILLE, TX, US

Guide - Brownsville

$100,000 USD/year
UNITED STATES

Reading Specialist

$100,000 USD/year
UNITED STATES

Lead Guide

$150,000 USD/year
MULTIPLE LOCATIONS

Guide

$100,000 USD/year
UNITED STATES

Lead Guide K-3

$150,000 USD/year
UNITED STATES

Guide K-3

$100,000 USD/year
REMOTE

Academic Advisor

$75,000 USD/year
GEORGETOWN, TX, US

Reading Specialist

$100,000 USD/year
AUSTIN, TX, US

Elite Guide

$150,000 USD/year
UKRAINE

AI-Driven Learning Analyst - Ukrainian Speaking

$60,000 USD/year
REMOTE

Director of Academics

$400,000 USD/year
REMOTE

AI-Driven Learning Analyst

$60,000 USD/year
AUSTIN, TX, US

Elite Guide

$150,000 USD/year
ARIZONA, US

Reading Interventionist

$60,000 USD/year
DRIPPING SPRINGS, TX, US

Lead Guide

$150,000 USD/year
DRIPPING SPRINGS, TX, US

Reading Specialist

$100,000 USD/year
DRIPPING SPRINGS, TX, US

Admissions Associate - Waypoint

$75,000 USD/year
NY, US

Community Builder

$150,000 USD/year
NY, US

Head of Enrollment

$400,000 USD/year
NY, US

Lead Founder Guide

$250,000 USD/year
NY, US

High School Elite Guide - Entrepreneurship

$200,000 USD/year
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Associate Dean of Parents - Bay Area @ Alpha

$250,000 USD/year
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California, US
Semi-flexible schedule
In-person
full-time (40 hrs/week)
Long-term role

Key responsibilities

Build and sustain deep trust with ultra-high-net-worth families, ensuring long-term retention, advocacy, and confidence in Alpha’s AI-powered education model.

Description

The families you know don’t need more services. They need someone they trust without question.

This role sits at the center of that trust. You will become the person families rely on when something feels off, when they need perspective, or when they want to share something that matters. Not because it’s your job—but because you’ve earned it. Your presence will shape how they experience their child’s education at one of two Bay Area campuses: San Rafael or downtown San Francisco.

Alpha is building a different kind of school. Students complete core academics in two hours a day using AI-powered platforms, then spend the rest of their time on public speaking, critical thinking, and real-world execution. No lectures. No busywork. Top 1% outcomes nationally. Our families are sophisticated, well-advised, and often skeptical. They expect clear thinking, not scripts.

You will guide that conversation over time. Not just at enrollment, but across years. You will speak fluently about AI—how it works, where it fails, and why it matters—especially with families who build companies, invest in them, or expect precision in every decision. If you cannot hold that level of conversation, this role will feel heavy. If you can, it becomes one of the most intellectually engaging roles in education.

This is not account management. This is long-term trust with ultra-high-net-worth families who expect discretion, judgment, and consistency. If that environment feels familiar—and you reach for AI daily to think, write, and operate faster—you will recognize the opportunity immediately.

Candidate requirements

  • Based in or able to commute daily to San Rafael or San Francisco
  • 5+ years working directly with UHNW individuals or families in private schools, private equity, family offices, or elite client service environments
  • Proven ability to navigate complex, high-stakes relationships with discretion and sound judgment
  • Active, daily user of AI tools (e.g., ChatGPT, Claude, Perplexity) with the ability to clearly explain AI capabilities, risks, and limitations
  • Strong presence and communication style that earns credibility with highly educated, high-expectation families
  • Familiarity with private or independent school ecosystems, either professionally or personally
  • Availability for early mornings, late afternoons, and select evening or weekend events

Frequently Asked Questions

Meet some of the 5,000+ rockstars who have found a rewarding remote career on Crossover.

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Join top-tier companies as a remote education, working full-time

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