A while back I signed up for a pingdom alternative. I was pretty happy with the interface and probably would've considered paying for some of the extra features.
However, I very soon after received an 'informal' message from the CEO or whatnot asking if I'm happy with the product and about upgrading the paid version. And whenever I logged in, a chat box would open with some first-name-basis employee asking me if I'm happy with the product and whether I'd be interested in upgrading. On top of that a number of the screens would have similar types of messages.
I've rarely experienced such aggressive on-boarding, and I implore every business owner to avoid doing so. Because as a result, I am less likely to upgrade to a paid version.