Dear SaaStr: How Do Startups Really Sell to Big Enterprises Before They’re Proven?

You solve their problems.  And you solve a specific problem that is important to your buyer — that the existing, current, proven vendors don’t solve well.

Large enterprises use lots of tools, widgets, and software in their businesses, but they tend to use the obvious, trusted solutions. At least 90% of the time.  They aren’t looking for a cheaper version of ServiceNow or a slicker version of Salesforce, for example.

But they are looking for two things, which allows start-ups to break though into big companies before they have brands:

  • True innovation in their core processes. Almost all big companies now have innovation departments of some sort, as do many divisions and groups. The general idea is to bring in 1–2 new vendors a year that don’t risk taking the core business down, but could have a material impact on the bottom line. If you truly can change the way they do business, you can often get a meeting. I’ve done this in both my start-ups in the earliest days with 10+ F500 companies in the first 90 days.
  • Solving certain top headaches. Big companies do have budget to solve their headaches. If your solution solves a procurement or sales or finance or HR or whatever headache, and you hit the buyer at the right time, you can get a meeting. And often a sale.

Is this hard? Yes.

Is it done all the time? Yes.

You have to hustle, have the team to back up the commitments, and be able to sell a long-term relationship.

But if you can, it’s done all the time. Start-ups penetrate and close F500 and G2000 customers in their first 1–12 months all the time.

And importantly:

  • De-risk things Let Big Companies do pilots first — paid pilots, but pilots.  Let them start smaller.  Let them try you out first in a less risky workflow, division, etc.
  • Be honest.  You can pretend you are a little bigger than you are, but not too much.  Don’t hide your financials or team size if you’re asked.  That undermines confidence.
  • Do very tailored, very personal outbound.  Spam rarely works in the enterprise.  Instead, research the top 100 potential buyers.  And slow down, and spend half an hour writing each email.  Do your research.  Tell them how you can truly solve a top problem for them.  If you do, there’s a good chance the email at least gets read.
  • Ask if “it’s budgeted.”  It’s OK to ask.  If it is budgeted, ask who else they are looking at, and why.  If it’s not budgeted, you can still win the deal.  It just likely has to come from a much small discretionary budget.  So maybe scale down the initial ask.

Some more great learnings here:

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