Why Most EdTech Sales Chaos Is Self-Inflicted

I used to wing every deal.

Different pitch for every district. Different approach for every conversation. No repeatable process.

Sometimes it worked. Usually, it didn't.

After losing enough deals, I realized the chaos wasn't the market. It was me.

The Pattern I Kept Seeing

After decades in EdTech, I started noticing the same pattern with founders I worked with—and in my own early career.

Smart people. Good products. Genuine passion for helping students.

But complete chaos in how they went to market.

Every pitch was custom-built from scratch. Every conversation felt like starting over. Every deal followed a different path—or no path at all.

They were working hard. Just not systematically.

And without a system, you're not building a business. You're just getting lucky sometimes and wondering why you can't replicate it.

What Chaos Actually Looks Like

Here's what I saw—and what I did for years myself:

Winging pitches instead of having a framework. Walking into meetings without a clear structure. Sometimes talking about features. Sometimes talking about outcomes. Sometimes, just reacting to whatever questions came up. No consistency. No repeatability.

Skipping discovery and jumping to demos. When a district expresses interest, you immediately show them the product. You assume you know what they need. You spend 30 minutes explaining capabilities they might not care about. Then you wonder why they go quiet afterward.

Hoping deals close instead of managing a process. You have conversations. You send proposals. Then you wait. And hope. And follow up. And hope some more. But you're not actually managing anything—you're just reacting to whatever happens.

I did all of this for years. Still catch myself doing it sometimes.

But the chaos this creates is exhausting. And expensive.

The Shift That Changed Everything

So I started documenting what actually worked:

• Questions that opened up honest conversations instead of polite brush-offs.

• Problems districts actually funded versus those they chose to ignore.

• Align solutions to their budget cycles instead of fighting against their timeline.

• Made long-term relationships stick versus fade after the first meeting.

Took years. But eventually, I had a process I could repeat.

Not because I'm smart. Because I got tired of starting from scratch every time.

What "Having a Process" Actually Means

When I talk to founders about process, I get two reactions:

Some think I'm talking about complicated CRM workflows and rigid scripts. Others think the process will make them sound robotic and inauthentic.

Neither is true.

A process isn't about removing humanity from sales. It's about removing chaos.

It's knowing what questions to ask in the first conversation so you're not wasting everyone's time.

It's understanding where districts are in their budget cycle so you're not pushing for decisions that can't happen yet.

It's having a framework for discovery so you actually understand their problems before you start pitching solutions.

Process doesn't make you less flexible. It makes you more effective.

Where Most Founders Get It Wrong

Most founders I meet start with their product and wonder why nothing's selling.

They've built something. Now they need customers.

So they start pitching. Cold outreach. Conference booths. Demo requests. Hoping something sticks.

Here's what I've seen work better:

1. Start with the problem, not the product.

2. Talk to districts about their number one pain point. 

3. Listen with empathy. 

4. Understand their issues.

Keep probing to identify the causes and more fully understand the problem.

Then—and only then—figure out if what you've built actually solves what they need.

Sometimes it does. Sometimes it doesn't. Sometimes it solves a problem you didn't think of.

Most founders skip that part. They think they already know what districts need because they built the product to solve what they assumed was the problem.

Then they wonder why deals take forever or never close.

The ones who consistently win? They start with understanding, not pitching.

The Questions That Actually Matter

After years of trial and error, I've learned there are questions that open doors and questions that close them.

Questions that close doors sound like pitches in disguise:

"Would you be interested in a solution that improves reading scores?"

"Are you looking for better data analytics?"

These are leading questions. Everyone knows you're trying to steer toward your product.

Questions that open doors sound like genuine curiosity:

"What's your number one challenge with reading intervention right now?"

"When you think about next year's budget priorities, what concerns you the most?"

"Help me understand what's working and what's not with your current approach."

These questions don't include your product. They're about their world, not yours.

And that's the difference.

When you ask about their problems without an agenda, people actually tell you the truth. When they sense you're just trying to pitch, they give you polite answers and move on.

What Changed for Me

Once I started following a repeatable process—one that prioritized understanding before pitching—everything shifted.

Conversations became easier. Not because I got better at talking, but because I got better at listening.

Deals became more predictable. Not because I could close faster, but because I could see earlier which opportunities were real and which ones weren't.

Relationships lasted longer. Not because I was more likable, but because I was more useful.

I stopped showing up with solutions and started showing up with questions.

I stopped hoping for lucky breaks and started creating conditions for predictable outcomes.

It didn't happen overnight. And I still mess it up sometimes—falling back into pitch mode when I should be in discovery mode, trying to rush deals that need more time, assuming I know what districts need without actually asking.

But when I stick to the process—ask the right questions, understand their world, align with their timeline—things go smoother.

Not faster. But more predictable.

And predictable beats chaotic every time.

Questions Worth Asking Yourself

If you're an EdTech founder struggling with inconsistent results, ask yourself:

1. Do you have a repeatable process, or are you winging it every time?

2. How much time do you spend probing to understand problems versus pitching your solution?

3. Can you describe the path from the first conversation to the signed contract, or does every deal feel like it follows a different, random path?

4. Are you tracking where prospects are in their budget cycle, or are you just pitching whenever someone shows interest?

These aren't comfortable questions. I know because I avoided them for years.

But avoiding them doesn't make the chaos go away. It just means you keep experiencing it, deal after deal.

The Hard Truth About Process

Here's what nobody tells you about building a repeatable sales process:

It's boring.

Documenting what works. Creating frameworks for discovery conversations. Tracking where prospects are in their cycle. Following up systematically instead of randomly.

None of that is exciting. None of it feels like the breakthrough moment that changes everything.

But that's exactly why it works.

Chaos is dramatic. Process is mundane. But chaos is also exhausting and unpredictable.

When you build a system—even a simple one—you stop reinventing everything from scratch. 

You stop wondering why some deals work and others don't. You stop feeling like you're just getting lucky.

You start seeing patterns. Understanding what works. Replicating success instead of hoping for it.

The founders who win consistently aren't the ones with the best product or the smoothest pitch.

They're the ones who figured out a process that works and had the discipline to follow it.

Even when it felt boring. Even when they wanted shortcuts. Even when chaos felt easier than structure.

Where to Start

If you don't have a process and want to build one, start simple:

Document the questions you ask in discovery conversations. Write them down. Refine them. Use them consistently.

Track each prospect's progress through their budget cycle. Know whether you're building for this year or next year.

Create a simple framework for qualifying opportunities. Not every interested district is a real opportunity. Know the difference.

Follow up systematically. Not randomly. Have a plan for staying engaged without being annoying.

You don't need a complex system. You just need something repeatable.

Because repeatable is what turns chaos into momentum.

And momentum is what builds a business that lasts.

What's one thing that made your sales process more predictable? I'm curious what's worked for others who've made this shift.