The Revenue Architect

The Revenue Architect

How to avoid extending pilots

Don’t make deadlines negotiable

Arnie Gullov-Singh's avatar
Arnie Gullov-Singh
Sep 24, 2026
∙ Paid

The pilot ended a month ago. The contract isn’t signed but the customer is still using it. Everyone is being very polite about this. But only one of you is getting shafted.

If this sounds familiar, you’ve probably had a customer tell you, “We love the product. Can we keep using it while the paperwork is sorted out?” It seems rude to say no but it’s no different from them asking, “We love your house. Can we live in it for free while we discuss whether we want to rent it?” You wouldn’t say yes to the latter. You shouldn’t say yes to the former.

This post covers six steps on how to avoid this happening. None of them are complicated but they are slightly uncomfortable, which is why this problem exists. Get comfortable being uncomfortable…

1. Define the grace period

Most pilot agreements say how long the pilot lasts and what it costs afterwards but very few say what happens at the moment it ends. It opens the door to an extension.

Decide in advance how long a grace period, if any you are going to offer. Don’t wing it and decide it deal by deal because you’ll get caught up in the emotion of hoping the deal will close.

2. Fire an in-product banner when the pilot ends

The ROI decision call typically marks the end of the pilot, so that’s when the banner should go up. It should be crystal clear about what is ending and what to do to maintain usage.

For example. if you are offering a 5-day grace period, the banner should say, “Your trial period ends in 5 days. After that you’ll lose access” and should decrement each day.

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