Why So Many Entrepreneurs fail at Sales (And How to Fix It)

Like it or not, sales is the most important part of every startup. Are you putting in the effort to get good at it?

I was chatting with a friend who also happens to be one of the most thoughtful sales leaders I know. During our conversation, he shared a counterintuitive strategy that helped him and his team increase appointment and close rates. He was contemplating hiring SDRs — Sales Development Representatives, the people who qualify customers early in a SaaS sales process — he never trained them on the product.
That’s right. The SDRs on his team — the first people potential customers would speak with — had no idea what the company’s product actually did.

At first, this sounds insane. After all, how can you sell something if you don’t even know what it is? But my friend had a good reason: Whenever SDRs were trained on the product, they couldn’t help but talk about it. They’d dive into features, capabilities, and specifications, trying to “sell” the product itself. And the moment they started talking about the product, things went south.

Potential customers would hear the pitch, make assumptions — often wrong ones — about what the product could or couldn’t do, and mentally un-sell themselves.
In other words, by having knowledge of the product, his SDRs lost sight of what really matters in sales: the customer. Instead of asking about the customers’ needs, goals, and problems, the SDRs were busy discussing a product prospective customers didn’t yet care about.

As I listened to my friend, I couldn’t help but feel ashamed. In that moment, I realized I’d been guilty of the exact same mistake — only worse.

Example; The Product Obsession That Made Me Suck at Sales
When I was building my startup and I was also the technical cofounder, meaning I personally wrote every line of code that powered our platform. I built it from scratch, and I knew it inside and out.
The codebase was like my baby, and that pride and love, unfortunately, was my downfall.

As the person who built the product, I couldn’t stop talking about it. I’d walk into sales meetings and immediately start pitching what I’d built. I’d tell potential customers how efficient our architecture was, how many features we’d built, and how cool and powerful the platform was.
It wasn’t an effective sales strategy. Even worse, I never understood why. All I could think was, “How can these people not see how cool my product is?”

In hindsight, my shortcomings are painfully obvious. My obsession with the product and its features blinded me to the people I was supposed to be serving. I was so busy showing off what I’d built that I forgot to ask whether anyone even needed it.

I’m an extreme example of a founder focused on what he’s building rather than his customers, but I’m definitely not the only one who’s made the mistake. Indeed, most entrepreneurs — whether they directly constructed their products or not — are obsessed with what they’re building instead of the people they’re building for.

Why Talking About Your Product Is a Mistake

Entrepreneurs love their products. We can’t help it. After all, we poured time, energy, and creativity into building something we’re proud of, and we want the world to see how amazing it is.
The problem with this obsession is that customers don’t care about products. At least, not when they first encounter them.

As a result, when you sit down with potential customers and immediately start talking about features, you’re asking those would-be customers to do too much mental work. You’re asking them to figure out how your product fits into their lives or solves their problems despite not really understanding what the product does or, in most cases, the extent of their own challenges. And if they don’t immediately see the connection, they’ll tune out. Worse, they might start imagining reasons why your product won’t work for them.

This phenomenon is why my salesperson friend learned to keep his SDRs in the dark about the product they were selling. When his SDRs didn’t know what the product did, they couldn’t talk about it. And when they couldn’t talk about it, they were forced to focus on the customers — on learning about their processes, their pain points, and their goals.

That’s the real work of sales. It’s not about pitching your product. It’s about understanding your customers so well that you can show them why they need your product in the first place.

The Mindset Shift Entrepreneurs Need to Make
If you want to stop sucking at sales, you need to adopt the same mentality as my friendl; You need to stop thinking like a product builder and start thinking like a problem solver.
Begin by asking questions. Lots of them.

What does the customer’s current process look like? What problems are they facing? How much is that problem costing them? What would success look like for them?

Sales is about listening more than talking. It’s about gathering information and then connecting the dots for whichever customers you’re talking with. Once you understand their needs, you can position your product as the solution to their problems. But until you’ve done that, talking about your product is just noise.
This mindset shift is hard for entrepreneurs — especially for founders who are also product builders — because we’re too close to what we’ve built. We see our product as a work of art, a reflection of our skills and ingenuity. But to a customer, it’s just a tool.

The elegance of the code and the number of features it has doesn’t matter. If the customers don’t see how your product solves their problem, they’re not going to buy it.
If you’re an entrepreneur struggling to sell, you need to learn to get over yourself. Stop obsessing over the product you’ve built and start obsessing over your customers. Sales isn’t about you. And it’s also not about your product, your features, or your architecture. It’s about the customers — what they need, what they’re struggling with, and how you can help them.

The best salespeople know this instinctively. They don’t sell products; they sell solutions. And if you can make that shift — if you can stop talking and start listening — you’ll stop sucking at sales.
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