Breaking Into Edtech

Jack McDermott
8 min readMay 2, 2023


Every few weeks, I’m introduced to someone who wants to find a job in edtech.

Some are teachers who want to scale their impact beyond the classroom walls. Many of them are burnt out. Others are MBAs or tech professionals searching for greater purpose in their work.

I’ve spent the last ten years growing new products in the edtech space; first on my own (speech therapy apps), then at Panorama Education (K-12 software), and today at Chegg Skills (workforce learning).

In this post, I’ll share a few tips for those looking to break into edtech.

Get to know the landscape

The education market is a big place. There are 50 million students, 3 million teachers, and $667 billion in total annual spending in K-12 alone. Global edtech spending is set to grow by ~25% annually post-pandemic.

Yet “edtech” is a catch-all term for a big market with several unique segments. Let’s divide the space into the following categories:

  • Early childhood & Pre-K
  • K-12
  • Higher education
  • Workforce learning / corporate training
  • Lifelong learning

Consider which edtech segment you’d most like to contribute to — your daily work, insights, and impact will look very different in an early childhood edtech company setting compared to one in corporate training.

This market map from Jennifer Phan follows a target learner’s age or stage in life from childhood through adulthood:

Understanding the Current Landscape and Future of Learning by Jennifer Phan

While I started my edtech career in the K-12 segment, I pursued my next role in workforce upskilling and reskilling. I narrowed my focus on companies working on lifelong learning, career mobility, and skills (Chegg Skills, Guild, Grow with Google, InStride, among others).

Each segment faces new opportunities ahead. Many disruptive trends stem from the COVID-19 pandemic, the rapid rise of generative AI, or the acceleration of decades-long cultural and socioeconomic shifts in American education.

Consider how innovations may solve for…

  • Early Childhood/Pre-Kunaffordability/staffing challenges in childcare, early learning apps
  • K-12 ChatGPT, homeschooling, education savings accounts, tutoring
  • Higher Edstudent debt, declining college enrollment, ChatGPT, job-ready skills
  • Lifelong learningemployee education benefits, upskilling & reskilling, STARs, job displacement from automation

Company Stage

Another helpful way to segment the edtech market is by company stage or business model. Are you looking for an early-stage Y-Combinator startup with < 5 employees or a publicly-traded company like Chegg, Pearson, Google, or 2U?

The earlier a company’s stage, the more of a generalist you’ll likely be. You may find early-stage roles as a “Client Success Associate,” compared to highly-specialized roles at bigger companies like “Product Manager, Consumer Services” or “Implementation Lead, Large Districts.”

You’ll encounter different company focus areas by stage, as well—from startup (~1–100 employees → find product-market fit), mid-stage “scale-up” (~100–1,000 employees → scale early success with new systems, prove your unit economics), to large/publicly-traded (~1,000+ employees → deliver predictable growth and profitability at scale).

Perhaps you want a fast-moving, high-autonomy environment with a small team, or maybe one with more intentional training, resources, and existing processes from which you can learn. Consider which environment best fits your work style and career goals at any time.

Business Model

Does your target company sell to consumers (B2C) like Duolingo or MasterClass, or businesses/school systems/institutions (B2B) like Instructure and Guild?

A company’s business model and customer type often dictate the way they’re organized and run. Working with large systems or businesses (B2B) comes with higher upfront effort/cost/time/implementation compared to serving learners directly (B2C). But serving consumers directly also introduces limits in discretionary spending/retention/buy-in/scale from larger organizations.

And like in healthcare, edtech companies most often serve multiple stakeholders at the same time. Teachers and students might be the users or beneficiaries, but school districts or state agencies might be the customers. Consider what you want your day-to-day to look like, and ask how companies serve different stakeholders.

While we all want to break in and start making an impact, understanding the edtech space will bring greater focus and clarity to your search.

Do your homework

I recommend deepening your knowledge of past edtech initiatives, school reform, VCs, influential edtech leaders, and recent news.

Education has its own terminology and complexities that are worth knowing about. And while edtech is having a moment more recently (edtech venture funding jumped ~300% in 2020–2021, reaching a record-high $8B), efforts to innovate in education are far from new.

Recommended Twitter Follows

Recommended Articles

** Hat tip to Matt Tower for sourcing additional recommendations

Recommended Books

Recommended Podcasts

Recommended Newsletters

Try the product

If your target company offers a product that’s available for you to try, download the app or create an account.

Start jotting down notes and ideas on what’s working well, what could be improved, and where your work could make an impact. Download highly-rated learning apps like Duolingo to understand which features and flows lead to a successful student experience.

When initially applying to Panorama, I scoured Twitter to find mentions of student surveys and social-emotional learning (SEL). I found tweets from educators and one state agency leader who discussed using student surveys that even Panorama wasn’t aware of at the time!

Try edtech products and form opinions of your own.

Locating target companies

Now that you’ve grown your knowledge of the edtech landscape, done your homework, and read up on seminal edtech reads, you’ll make smarter, more relevant connections with target companies.

If you’re interested in early-stage edtech companies, tracking venture funding announcements and VC job boards will give you a leg up. Keep an eye on edtech funding announcements; startups typically hire after raising venture funding.

Because there are seemingly infinite numbers of job search sites (LinkedIn, Indeed, ZipRecruiter, etc.), I recommend several edtech-specific job boards.

Recommended Edtech Job Boards

Sending cold emails

My first step into both Panorama and Chegg started with cold emails. A personal touch goes a long way in building connections, especially when hiring managers see hundreds of applications per open role.

A snippet from my first cold email to Aaron, CEO at Panorama

Explain why you’re passionate, what you’ve done that’s relevant, how you found their contact info, why you’re interested in talking, attach relevant links, what you hope to learn, and when you’re available to chat.

Connect personally with your target contacts via cold email or LinkedIn. Not every role that’s needed is posted on a company’s jobs board.

Getting past imposter syndrome

Education is one of the few industries where we’ve all been consumers throughout our lives. Remember the name of your first-grade teacher? Me, too.

This can be both a blessing and a curse; we might think we know how edtech should work best, but there are few longitudinal efficacy studies or randomized-control trials that prove what’s best. It’s best to be humble.

I often hear job-seekers say, “But I’ve never worked in the space before.” Yet I’ve seen former teachers become star sales reps and client success managers, and recovering academics or fintech engineers become impactful data scientists.

Communicate how your underlying skills and experiences map onto those needed for success on the job.

You get the idea. By identifying your core skills for the role, you can bridge any perceived gaps for hiring managers instead of hoping they see the connections on their own.

Parting thoughts

As I wrote in Inside the Edtech Hourglass, there’s no right or wrong approach to getting involved in education innovation. What we need most are good-intentioned builders.

There are no shortcuts or hacks for finding your ideal role. It will take time. I recommend you take the time, go deep, do your homework, talk to those with experience, form your own opinions and revise them often.

And if you have any questions, feel free to reach out along the way.




Jack McDermott

Growth @ Chegg Skills. Previously: MBA & M.Ed, UVA Darden, @PanoramaEd.