Dear SaaStr: How Can an Early Stage SaaS Startup Get its First 1-3 Pilot Fortune 500 Paying Customers?

It’s not magic.  And it’s not a mystery.  Even though it can seem like it, until you’ve done it yourself.

There are basically two paths, and one predicate step

The predicate step is your product has to do >one< reasonably important thing that is 10x better than the “enterprise”-proven solutions already out there.

So much better, just this one thing, that it’s worth it for a BigCo to take a risk on using you, not Salesforce-Oracle-Microsoft-Box-SAP-whatever.

If it’s not 10x better, no one is going to take the risk.

This doesn’t mean everything in your product is 10x better than the competition (of course). Just one important piece of it.

Related to this, the risk needs to be measured.

No one is going to rip out Workday or SAP to try your product. The risk needs to be able to be contained. To one small group. One addition to a business product. Somehow — contained.

OK, so you have a feature-poor, insecure, buggy product but it does one interesting, important thing 10x better than all the legacy providers (which could also be paper or Excel) and can be tried without putting a job at risk.

So how do you get those customers?

Outbound or inbound.

You call call / email them (this is how I landed my first F500 customer in my first start-up).

Or you can wait for them to come to you. The top industry tradeshows sometimes actually work well here.  The top buyers go to them, in part, to meet top new emerging vendors.  So does an insane amount of PR (this is how I did it the second time).  So do CIO-style pitch competitions that VC firms and similar do, if the audience is strong.

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