Why Some EdTech Companies Last and Others Don't: What I Learned Watching Companies Come and Go for Decades

Forty years in EdTech. I've watched a lot of companies come, and a lot of companies go.

Most didn't fail because of bad products.

They won a contract. Threw a party. Started chasing the next one.

Meanwhile, the district they just signed was struggling. Teachers didn't know how to use it. Principals had questions. Nobody from the company is picking up the phone.

When the renewal came around, the district said “no thanks.”

The companies that are still around? They did it differently.

The Pattern I Kept Seeing

Early in my career, I thought winning contracts was the hard part.

Get in front of the right people. Build a compelling demo. Show a clear ROI. Handle objections. Close the deal.

That's what I focused on. That's what everyone focused on.

And then I started noticing something interesting happening.

Companies with worse products were outlasting companies with better ones. Vendors with smaller teams were securing renewals, while larger, better-funded competitors were losing accounts.

It didn't make sense until I started paying attention to what happened after the contract was signed.

What Happens After the Celebration

Here's the pattern I saw with companies that disappeared:

They'd win a district. Big celebration. Team high-fives. Maybe a press release. Then everyone moved on to the next opportunity.

The district that just signed? Now they're on their own.

Implementation started. Questions came up. Teachers got confused. Principals needed support. The product wasn't working the way everyone expected.

The company? Chasing the next deal. Too busy to answer calls. The implementation team is overwhelmed, and customer success is buried in tickets.

Six months later, the product was sitting there unused. Teachers had given up. Administrators had moved on to other priorities. Students were clicking through because they had to, not because it was helping.

When renewal time came around, the district didn't even consider it. They were done.

I watched this happen over and over. Different companies. Different products. Same pattern.

What the Companies That Lasted Did Differently

Then I started watching the companies that stuck around for years. The ones districts renewed again and again. The ones that became part of how districts actually operated.

They did something different after signing the contract.

They stayed through implementation. Not just the first week. The whole messy process of getting teachers trained, working through technical issues, and figuring out how it actually fit into daily practice.

They actually answered calls. When a teacher had a question three months in, someone picked up the phone. When a principal needed help explaining it to the board, someone showed up.

They made sure it worked. Not just that the software ran, but that it was actually helping students. That teachers could use it without adding hours to their day. That administrators could show impact.

They were still there three years later. When everyone else had moved on to newer, shinier products, they were still checking in. Still supporting. Still making sure it was working.

That's what separated the companies that lasted from the companies that disappeared.

The Hard Truth About Longevity

Here's what nobody wants to hear: launches are easy. Sticking around is hard.

Winning the first contract is exciting. There's energy. Momentum. Everyone's motivated.

Year two? Not exciting. It's answering the same questions. Solving the same technical issues. Helping the same administrators explain value to their boards for the third time.

Year three? Even less exciting. But that's when you find out if you built something that lasts.

Because staying power isn't about the product, I've seen amazing products fail. I've seen average ones thrive for decades.

It's not about marketing either. Some of the flashiest brands I've known are gone. Some of the quietest ones are still growing.

It's about showing up. After the sale. When implementation needs support. When a teacher has questions six months in. When things are going fine and you check in anyway.

What I Used To Get Wrong

I would lose track of this at times.

A new opportunity shows up. Gets my attention. Suddenly, I'm thinking about the next deal instead of taking care of who's already here.

District reaches out about expanding. I get excited about growing the contract, and forget to make sure the current implementation is actually working.

Conference season comes around. I'm focused on demos and meetings with prospects. Current customers? They can wait.

Then renewals come up. And I'm surprised when a district doesn't renew. Or renews but doesn't expand. Or renews reluctantly.

Because I stopped showing up. Got distracted by what was new instead of staying focused on what already existed.

Every time I catch myself doing this and refocus on current districts, everything clicks better.

Renewals happen smoothly. References come easily. New districts reach out because someone mentioned us.

Not flashy. Just steady. And steady is what lasts.

The Question That Changed How I Think

A superintendent asked me, "If you disappeared tomorrow, would we even notice?"

She wasn't trying to be mean. Just honest.

Made me think about all the EdTech products sitting in districts right now. Purchased with good intentions. Barely used. Would anyone notice if they vanished?

Probably not.

Then there's the other kind. The tools teachers open every morning. The data administrators actually use. The programs that became part of the district's operations.

Those that disappear? The district is scrambling to find a replacement.

That's what I think about now when working with districts.

Not just: can we win the contract?

But, are we actually helping them do something they couldn't do before? Are we becoming essential to how they work, or just another login they ignore?

Big difference.

What Actually Matters

Over the past forty years, I've noticed that products don't determine who survives.

Seen great products that don't make it. Seen good ones last decades.

Marketing doesn't either. Some brands fade fast. Others keep going quietly.

What matters is showing up after the sale.

Not once. Not for the first three months. But consistently. Year after year.

When implementation needs support. When a teacher has questions. When things are going fine and you check in anyway.

Year three, when competitors have moved on to shinier things. Year five, when everyone else chased the next trend. Year ten, when you're one of the few vendors they still trust.

That's what builds companies that last.

Not better products. Not better marketing. Just showing up. Consistently. Even when it's not exciting.

Why This Is Hard

Nobody starts a company thinking "I'm going to be mediocre at launches but excellent at follow-through."

Everyone wants the exciting part. The wins. The growth. The new opportunities.

Follow-through is boring. It's answering the same questions, solving predictable problems, and showing up when there's no new business on the line.

But boring is what works.

The companies still standing after twenty years aren't the ones with the best product launches.

They're the ones that didn't disappear when things got boring.

They answered calls in year three. They showed up to help with implementation in year five. They were still checking in when everyone else had moved on.

That's not exciting to write about. It doesn't make for good conference presentations. It won't win awards.

But it's what builds companies that districts actually trust. And trust is what creates renewals. And renewals are what build businesses that last.

What This Means

If you're building an EdTech company, ask yourself:

What happens after your customers sign? Do you stay engaged or move on to the next opportunity?

When a district has questions six months in, do you answer quickly, or are you too busy chasing new business?

If you disappeared tomorrow, would your current customers scramble to replace you or barely notice?

Three years from now, will you still be checking in with districts you signed today?

These aren't comfortable questions. I avoided them for years because I was too focused on growth and new opportunities.

But avoiding them doesn't change the answer. It just means you find out at renewal time instead of having time to fix it.

The companies that last aren't the ones with the best launches. They're the ones who are still there when everyone else moves on.

Launches are easy. Sticking around is hard.

But sticking around is what matters.

What helps you stay focused on current customers when something new catches your attention? I'm curious what works for others navigating this tension.