We have all been there: your first big customer signs up and you get a taste of the good life. Now you want to get more of those bigger, more sophisticated customers.

It’s a trap. Believe me, I made this mistake TWICE.

Let me explain

The problem is that most companies try to go up-market too soon. 

They try to sell to enterprise customers before they have really figured out how to sell to their core customer.

You see, selling to enterprise-sized businesses is a totally different ballgame.

If you have found product-market fit in the SMB or mid-market space, you have built everything about your business to fit that market.

Your go-to-market motion, your product, your customer experience, and your messaging are all designed to support your core customer.

Enterprise customers have different wants and needs. They buy differently. They take longer to make decisions. They care about different features. They use a different language within their business.

Reid Hoffman said “Starting a company is like throwing yourself off the cliff and assembling an airplane on the way down.

Well trying to sell to two different customer segments is like flying two planes at once.

‍You can’t fly two planes at the same time.

This cannot be understated.

You can’t be an SMB company and also sell into the enterprise, at least not in the early days.

There’s a graveyard of early-stage companies that have tried to sell across customer segments before they were ready.

Yet, the allure of moving up-market seduces CEOs and VPs of Sales to make big bets on getting more of those enterprise companies.

It’s so hard to resist. That’s because there’s a lot to like about selling to Enterprise companies:

Getting those “sexy” enterprise logos makes us feel good.. They make the company look better and more sophisticated.

Also, the economics are just better. Enterprise companies pay big $$$ to solve problems, the revenue is sticky, the contracts are long-term.

Selling to enterprise businesses makes your own business more durable.

Why is it so hard to sell to enterprise companies?

Here are 6 reasons why:

1. How you sell to enterprise customers is totally different from how you sell to SMB or Mid-Market.

2. The customer use cases are usually different. How they use the product and the problems they solve, even the personas are different.

3. It’s more expensive to acquire the customers and it takes longer to close them.

4. When you try to sell up-market and down-market at the same time, you confuse your customers. You can even confuse the sales team for where they should focus their time.

5. You go up-market too early, before your core go-to-market is working

6. You quit before the miracle happens. It takes 12+ months of consistent effort to really get the motion working.

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So if you are thinking about moving up-market, be aware of the headwinds.It’s not impossible, and there are many successful companies that sell across customer segments. But pay attention to the timing.The most successful companies get their core GTM really working before they try to move into a separate customers segment.