I was like you. Then because of being contacted so much by sales (hmm, should we call them account exec or customer success, I'm always lost with those subtle terms) I tend to get used to it... as long as it's reasonable.
Here's my point: as a service user, I understand they need to get money to run the service, and so they try to make us pay for the non free-tier. That's fair. But when I start playing with a tool/product/service, if I haven't answered your 'hey let's have a chat and see how we could help you' first email, then the second (and 3rd, ...) ones are not likely to get more responses. And when I actually need to talk to find out more information about pricing/feature/missing doc, the first email is still there (even if in the trash, it's deleted after 3o days, which is usually the same period as the trial, if not more)
So back to your question: I don't mind a poke, that's part f the game. But repetitive requests give me a bad impression (ok, you're clearly not here to help, but more to get my money)
As with everything, it's not black or white, everything is in the nuance and the context ;-)