Dear SaaStr: What Was it Like Acquiring Your First Customer?

I had very different experiences in each of my startups.

In my first start-up, we were whale hunting — big, large, Fortune 500 customers. So Customer #1 showed us the path to our future.

My first customer signed a $10k contract (a small pilot) but our second, their competitor, then signed a $6m (multi-year) contract. When you are hunting Very Big Deals from a small number of huge customers, and you close even one — you can see the future. It’s exciting.

The second time, we started SMB. We were hunting thousands of customers. It led to disarray, as we couldn’t agree on our ICP.

As a founding team, we didn’t know what to make of our first SMB customers, as they were very small — from $12 to $99 a month. What use cases did they really represent? How large were their markets? We had disagreements over what verticals they really were in, and how well suited we were to those verticals.

We also didn’t spend nearly as much time with the high volume of SMBs in my second start-up as we did (in person) with the small number of big Fortune 500 customers and prospects in the first one. Because we didn’t spend any time in person or enough time on the phone, we didn’t learn as much about them.

My learning: with very small businesses, you may need 20, possibly even 50, paying customers to have enough data to draw true opinions on what the future holds. There is so much diversity in the types of businesses SMBs run, how they run them, etc.

But with big enterprise customers, even 1 can show you the future. If you just listen. One Fortune 500 customer in a given industry/vertical is a lot like the others, typically.


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