Why Founders Struggle with Sales (And How to Fix It)

Let’s be real—most startup founders struggle at sales. And that’s not a knock on them.

They’re usually product-first, problem-solving geniuses, but when it comes to pitching, prospecting, and closing deals? That’s where things get messy.

And it makes sense. Sales isn’t just about explaining your product—it’s about positioning it in a way that gets people to buy. Founders often overcomplicate messaging, pitch to the wrong people, and fail to create urgency.

If that sounds familiar, don’t worry—you’re not alone. Here’s why most founders struggle with sales and how to fix it so you can close more deals without burning out.

1. You’re Over-Explaining

The Problem:

You built the product, so naturally, you want to tell everyone about every single feature. You’re proud of it! But the harsh reality?

Buyers don’t care.

They don’t want a list of features. They want to know:

What problem does this solve for me?
How does it make my life easier?
Why should I care right now?

If you’re spending 90% of your pitch explaining “how it works,” you’re losing deals before they even start.

How to Fix It:

Flip your messaging: Lead with the problem, not the product.
Use customer-centric language (stop saying “our AI-powered tool…” and start saying “you’ll never have to waste hours doing X again”).
Boil it down to the core outcome: “In 30 days, this will [increase revenue/reduce costs/save you time] by X%.”

Example:

❌ “Our software integrates seamlessly with existing workflows to provide advanced analytics on customer behavior.”

✅ “We help e-commerce brands increase repeat purchases by 30%—without changing a thing about how they sell.”

2. You’re Talking to the Wrong People

The Problem:

You’re pitching to anyone who will listen instead of the people who actually have the budget, pain, and authority to buy.

If you’re getting:

“This sounds cool, but it’s not a priority right now.”
“We don’t have the budget.”
“Let me check with my team and get back to you.”

…you’re probably talking to the wrong person.

How to Fix It:

Define your Ideal Customer Profile (ICP). (Not “anyone with a credit card.” Be specific.)
Target decision-makers, not just users. (Users might love your product, but they’re not the ones who sign contracts.)
Qualify hard—don’t waste time on “interested” people who will never buy.

3. You’re Not Creating Urgency

The Problem:

You assume that if someone likes your product, they’ll eventually buy. Wrong.

Liking something isn’t enough. Buyers need a reason to act now—otherwise, they’ll kick the can down the road… forever.

How to Fix It:

Show the cost of inaction. What happens if they don’t buy today? Lost revenue? Wasted time? Falling behind competitors?
Use real urgency, not fake pressure. (“We only have 5 seats left” is weak. “Companies who implement this now are seeing a 2X ROI in the first 90 days” is strong.)
Follow up like a pro. 80% of deals require at least five follow-ups, but most founders give up after one.

Example:

❌ “Let me know if you’re interested.”

✅ “Most of our customers are closing this gap within 60 days—do you want to move forward before [competitor] does?”

4. You’re Trying to Sell Like a Salesperson

The Problem:

You think you need to act like a traditional salesperson to close deals—overly polished, pushy, and robotic.

But buyers see right through that. They don’t want a sales pitch. They want to talk to an expert who understands their problem.

How to Fix It:

Ditch the generic sales talk. Be real. Be helpful.
Focus on consultative selling—diagnose their problem and show them a solution.
Use social proof—case studies, testimonials, and data to back up your claims.

5. You Don’t Have a Repeatable Sales Process

The Problem:

If you’re winging every call, sending random follow-ups, and treating sales like an afterthought, you’ll never scale.

A predictable sales process = predictable revenue.

How to Fix It:

Create a structured sales playbook. (Discovery questions, objection handling, follow-up sequences.)
Use a CRM. Stop tracking deals in your inbox—HubSpot, Pipedrive, or Apollo will change your life.
Systemize follow-ups. 44% of salespeople give up after one follow-up, but 80% of deals take at least five. Stay persistent.

Example:

❌ Randomly checking in: “Hey, just following up to see if you had any thoughts.”

✅ Structured follow-up: “Hey [Name], last time we spoke, you mentioned [problem]. Our customers typically solve this within [timeframe] and see [impact]. Want to chat this week?”

Final Thoughts:

Fix Sales, Close More Deals

Most founders don’t struggle with sales because their product is bad. They struggle because they:

Talk too much about features (instead of outcomes)
Target the wrong people (who will never buy)
Fail to create urgency (so deals drag forever)
Try too hard to “sell” (instead of solving problems)
Don’t have a repeatable process (so revenue is unpredictable)

The good news? You can fix all of this without becoming a “salesy” founder.

Get your messaging dialed in, talk to the right people, create urgency, and follow a process. That’s how you go from struggling to closing deals predictably.

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