I handle sales at a small B2B software company, and we're trying to get a better handle on our pilot process before it gets too messy. We sell reporting software, and prospects usually want to test it with their own data before committing. The tricky part is that it's not really a self-serve trial. Someone from our team often has to help with the import, get the first report working, and follow up when they run into issues.

We're tracking deals in our CRM, but it's hard to get a clear picture of how much time we're spending on pilots and which ones actually turn into customers. Some leads move through setup quickly, others go quiet halfway through, and sometimes we only realize how much work went into a pilot when we're looking back at the deal.

I'm considering setting up a more structured process to track each pilot's stage, setup tasks, blockers, and outcome. We might also start charging for pilots that require a lot of hands-on work, but I'd want to understand our conversion rates first.

For those running B2B sales through a CRM, how do you track pilots from the initial request through setup and conversion without creating a ton of admin?