EdTech Jobs in Chicago, US

A career in school and education shouldn’t come with burnout, bureaucracy, and financial struggle. If you're tired of low pay, endless grading, and unrealistic expectations, it's time to consider education tech jobs on Crossover.

We offer elite roles in education that let you focus on what you do best while earning 1.5x to 3.8x more than the national average.

Our educational technology roles start at a cool $100K and climb as high as $400K - far beyond what most educators and supporting staff can expect in their careers!

Higher Pay, More Stability

Public school teachers earn between $50K–$70K per year in the US.

We don’t have to tell you your pay doesn’t keep up with inflation, cover the bills, or give you the lifestyle you’d prefer. Too many educational professionals have to work second, even third jobs.

Not on Crossover – our clients pay education pros what they’re worth.

Our EdTech Clients Pay:

• Guides (equivalent to a teacher) start at $100K
• Lead Guides (equivalent to senior teacher) earn $150K
• Heads of Academics (equivalent to head of department) make $200K
• That’s up to 3.8x more than traditional teaching pay!
• National US Average for teachers ($69,597) - 1.4X, 2.2X and 2.9X more

National Averages By Location (And How Much More Crossover Jobs Pay)

• Texas ($60,716) / 1.6X more / 2.5X more / 3.3X more
• Florida ($53,098) / 1.9X more / 2.8X more / 3.8X more
• Arizona ($60,275) / 1.7X more / 2.5X more / 3.3X more
• New York ($92,696) / 1.1X more / 1.6X more / 2.2X more
• Louisiana ($54,248) / 1.8X more / 2.8X more / 3.7X more

No More Unpaid Overtime

No more evenings spent grading, lesson planning, or answering emails at midnight. We pay you for your expertise, not for administrative tasks that can be automated.

Many of our private client schools use educational technology that auto-grades – freeing you up to focus on the mentoring, guiding, leading or building side of education.

Career Growth Without the Red Tape

Traditional school systems offer limited (if any) career growth unless you take on more stress and more work. In our EdTech jobs, your performance - not politics - determines your career trajectory.

A year or two to Head Guide, and if you really smash it – you could even get your own school location to run. We’re not joking!

Teaching Without the Chaos

Adios overcrowded classrooms, standardized testing pressure, and endless distractions. Our client’s education models let you teach with purpose and focus on real student success.

We’re talking about smaller classes, one-on-one mentoring, automated testing and leading the way to making room for more important things: like field trips, unique programs and personalized challenges for kids.

Join an Elite Network of Educators

Crossover hires top-tier educators and pays them what they’re worth. After all, they’re helping create the first generation of AI-literate kids. 

If you're an innovator in education looking for better pay, better working conditions, and a real career path, it's time to step into an Ed Tech role worth doing.

Education isn’t what it used to be - thankfully. If you’re ready to ditch outdated methods and help redefine how people learn, you’re in the right place.

We’re looking for bold professionals who see education technology as a game-changer, whether you’re a seasoned educator or a specialist from another field bringing fresh perspectives.

If you’re passionate about mentorship, innovation, and pushing education forward, we have roles where you will make a serious impact.

Is This You?

• Corporate Trainers & Learning Designers – If you've built killer training programs and want to bring that expertise to EdTech, we want you.
• Education Consultants & Academic Coaches – You know what makes students succeed - now imagine applying that to scalable digital solutions.
• Instructional Designers – You don’t just throw content together - you architect learning experiences. If you’re an e-learning and pedagogy pro, we need you.
• AI & EdTech Enthusiasts – If AI-driven, personalized learning keeps you up at night (in a good way), let’s put that passion to work.
• Education Policy & Research Experts – Big-picture thinkers who use data to shape the future of learning - this is your stage.
• STEM & Subject Matter Experts – Got deep school district knowledge in science, tech, engineering, or math? Help create next-gen learning solutions that actually stick.
• Higher Education Professionals – Professors, Deans, and administrators tired of academia’s red tape? Step into a dynamic, high-impact EdTech role where you can drive real change.

Use your expertise to do more than just teach - inspire, mentor, and shape the next generation of learners.

Our client schools are all about using innovative teaching methods and cutting-edge digital tools to create engaging, future-proof learning experiences - using the 2 hour learning model.

You'll be working on high-impact, long-term initiatives with some of the smartest minds in education, redefining how knowledge is delivered and absorbed. 

If you're ready to leave a lasting mark on the future of learning, this is where it happens.

At Crossover, we don’t just hire education consultants, designers, technologists and leaders - we identify and invest in the top 1% of talent in this critical space.

Our skill assessments are designed to surface individuals who are not just qualified but truly exceptional in their fields. The best people deserve the best jobs in EdTech.

Here’s what you need to work with our Ed Tech clients:

• A degree in Education, Psychology, or a related field
• Strong background in pedagogy and current educational technologies
• Experience in curriculum development, online education, or instructional design
• Excellent communication and interpersonal skills to engage students
• A passion for transforming education through technology and innovation

You'll also need to pass the cognitive aptitude test and a series of skill tests. 

Whether you’re stepping out of a traditional classroom, corporate training, or deep into instructional design, we’ll connect you with high-impact education positions where your expertise actually makes a difference.

You’ve found the best jobs in EdTech - but can you land one?

Apply now!