How Founders Should Sell (Hint: It’s Not About You)

Stop Asking “How Do I Sell?” and Start Asking This Instead

Most founders didn’t become entrepreneurs because they love sales.  
But once the product is live and it’s time to grow… suddenly you’re the head of revenue.

So you ask the most natural question in the world:

“How do I sell?”

I posed that exact question to Mike Dowhan, a seasoned VP of Sales and one of UpSuit’s expert advisors.  
His answer?

“Selling isn’t about how you sell. It’s about how your customer buys.”

That one insight reframes everything.

The Founder Sales Blind Spot

Most founders don’t come from a sales background.  
They built something great, but were never taught how to pitch, qualify, or close.

So they wing it.

But winging it leads to:

• Unpredictable sales
• Messaging that misses
• Long sales cycles with no close

Mike reminded me: you’re not bad at sales—you’re just focused on the wrong person.

Sales Isn’t About You. It’s About Them.

When a founder asks, “How do I sell?”, what they often mean is:  
“How do I convince someone to buy what I built?”

But here’s what works better:

“How does my customer make buying decisions—and how can I support that?”

This mindset shift changes:

• Your messaging
• Your team structure
• Your sales process
• Even your product roadmap

It moves you from pitching… to partnering.

The Top 3 Reasons People Buy

Mike laid it out clearly: every business buyer is driven by one or more of these:

1. Can you help me make money?  
2. Can you help me save money?  
3. Can you help me manage risk?

If your offer doesn’t connect to one of these drivers, you’ll struggle to close deals, no matter how good your deck looks.