This week I listened to an entrepreneur explain an interesting situation with a large pilot customer. He’d had a six-month contract for a paid pilot with a large company. The idea was for the company to test his software and then agree to a longer-term contract. Because of internal dynamics at the large company, the pilot ended without a new contract being signed. So, the entrepreneur disabled the customer’s access to his software platform.

An interesting thing happened. The company reached out and asked if they could still access the platform while they worked toward another contract (which was expected to take several more months). Said differently, they wanted access to the platform again even though a new contract hadn’t been agreed upon and they weren’t paying the entrepreneur. The entrepreneur was in a tough spot because he didn’t want to say no and jeopardize ongoing contract negotiations. But he didn’t want to get the large company used to accessing his software for free either. He wasn’t sure whether to grant them access as a good-faith effort or to ask for advance payment.  

While this situation didn’t feel great to the entrepreneur, I viewed it as an overall positive that showed his software is valuable to this large customer. A classic product–market fit question is “What would you do if this service or product went away?” If the customer is unbothered, then you know the solution is a nice-to-have; they can live without it. You either don’t have product–market fit or the problem you’re solving isn’t painful enough to the customer. Neither is a positive sign. If the customer is worried about it going away, that’s a great sign that the solution solves a serious pain point and is a must-have for them. A very strong signal.

This founder’s situation went a step further. When he disabled access, his large customer requested that it be restored. To me, this is a sign that his software is solving a serious pain point for that customer. They’d grown used to his solution, and when it was removed, the pain was real and they realized how much they needed it. The sequence of events that led to this wasn’t ideal. Rolling the pilot into a new long-term contract without service disruption would have been ideal. But if I had to bet, I’d say this customer will end up agreeing to a longer-term contract with this entrepreneur.