Answers · Enterprise deals
How should a startup run its first enterprise pilot?
A first call ends without much. The buyer doesn't have the information you wanted, and you don't have theirs. So you say the easy thing: "I'll send you a login. Try it out."
Now they have your product, and you have nothing. No problem in their words, no name of the person who can say yes, and no next step they own.
Trials confirm. They don't sell.
To me, the point of a trial is simple. The buyer has decided this is the right solution and wants to make sure it works before they buy it. Using one earlier, to get them to love the product, may be a valid move. Just think about why you're doing it and whether it's the best next step. Trials don't sell things. Trials confirm what we already thought.
An enterprise pilot is a trial with more people watching, so the same rule applies.
Agree on what success means before it starts
Ask under what criteria they would consider this a success and move forward. Use the success criteria they will actually accept, not the slide you wish they used. If nobody on their side can say what good looks like, the pilot can't prove anything. That's the S in SCALE.
Match the commitment
A pilot costs you time. Ask for the same level of commitment from them. Before you run it, say out loud who owns the decision, what good looks like, and what happens if it works. If they won't answer, that's an honest "this isn't a priority," and that's a gift. A pilot that only commits you lets them walk away with everything they needed and nothing they owed. That's equal commitment.
Run it with the people who decide
A pilot with one happy user is still one person. The stakeholders you haven't met are the ones who will say no to your person. So run the pilot alongside the next step, not instead of it. Use it to get other people involved. You're selling to the company, not the person. See One person loved the demo. The company never decided.
Not serious yet? Send a video
If the buyer is curious but has no real reason to change, a pilot burns your time and theirs. Rather than a demo and a trial and wasted cycles, send a short video of how it works. It keeps you in front of them, and other people at that company can see it too.
Common follow-ups
Should a startup offer a free trial to enterprise buyers?
It can, when the product is low value and low risk. Just think about why you're doing it and whether it's the best move for the next step. A trial confirms a decision. It rarely makes one.
What should be agreed before an enterprise pilot starts?
The success criteria the buyer will actually accept, who owns the decision, and what happens if the pilot works.
What if the buyer won't commit to anything before the pilot?
Treat it as an honest "this isn't a priority." That's useful to know early. A pilot that only commits you lets them walk away with everything they needed and nothing they owed.