My first enterprise pilot fell apart at the demo and I almost packed it in

The CEO's IT guy found a permission error in our SSO integration 10 minutes before we went live in front of 6 decision makers at a Boston logistics firm, we pulled the plug and rescheduled for next Friday, but has anyone else had a failed pilot turn into a stronger contract after you fixed the real objection?

1 comments

1 Comment

jesse_cooper13h ago

The part where you pulled the plug ten minutes before going live is actually the smartest thing you did, even if it felt like a failure. Most people would have tried to stumble through it and made the whole thing worse. What nobody talks about is that a permission error like that is almost never just a permission error. It usually means the IT person found something they didn't trust about your setup, and fixing that trust gap matters more than the demo itself. When you go back next Friday, that same IT guy is going to be watching to see if you actually learned the lesson or just patched the symptom. If you show him you rebuilt the integration with his concerns in mind, he becomes your advocate instead of your gatekeeper. That’s the real win, the demo is just the formality after that.