Great post, Greg!
We’ve experienced many of the same challenges working on Howdy. I only recently started automatically emailing deactivated users with a simple “sorry to see you go” email that asks what drove them to disable their bot.
To my surprise, many people will take two minutes to respond and tell you why they’re deactivating your service. Some of these people were just experiencing bugs that we were able to resolve for them! Would definitely recommend you get that going as soon as you can. I wish I had it running since we launched.
I have also experimented with re-engagement emails to some of our earliest beta signups and found that it was very successful in getting some of those teams to activate…with a lower-than-expected unsubscribe count, too!
TLDR; @email++ 😊