So, I kind of work in this space. On websites you can have prompts or call to actions that get triggered after a certain amount of time or scroll position or page being looked at etc. These will show a "new message" in the chat bubble to say "can we help you with anything?" I don't particularly find this invasive but I do find it annoying as I do usually know what I'm looking for when going to a website. However, I know, as you agree, companies use these techniques to upsell and gain increased online sales. And they work.
Then you raise a second point about emails. This would be completely different as the business in question would be contacting/spamming you directly. This scenario will soon be covered by GDPR, in the EU, so this will be less of a concern as of 25th May 2018 for EU citizens. I don't know think the prompts in the first case would be affected by GDPR, as long as the data isn't stored anywhere, but it might still fall under the "processor" business type covered in GDPR.
I guess there is also a psychological aspect to this as well. If you prompt users during their "session" then it can provide instant gratification as the visitor doesn't have to do anything, and the chat bot/agent will do it all for them.
tl;dr I think their is a balance, if the prompts are intelligent enough to know when, 9 times out of 10, a user is stuck then all good. But if a company is using it these kind of tools without any thought to the end user then they need to re-evaluate how it values its users.
So now I got several answers :) I think it's time for the discussion before I forget.
The emails, they are basically regulated you can sue any company that sends you an unwanted email in the U.S as well as in the EU
That's the right of privacy, but ofc they pester you 'at home' which is a different thing.
About the instant gratification, I actually used it once, they answered 2 hours later ;D .... which defeats the point of a chat-bubble. Because I can write to a contact form as well.
And I don't mind the chat bubble I mind the 'hey can I help you' pop up with the sound. as Joe Clark or Marco Alka mentioned a subtle approach one / good UX is not an issue.
But the general pestering seam to increase and even on a professional level. I know balance is hard and B2B vs B2C is important factor as well.
So as Mark mentioned the freedom to do everything with consequences. Which to some degree is a fair point but there is also as always a limit, for example exploiting psychological weaknesses. Which for example are shaming techniques.
The main issue is perspective to me.
For a company the goal is to sell something, so everything that makes them reach the goal is good. There is usually no to little moral unless enforced by the government.
For a citizen / an individual there are different rules, to get tricked into spending money is a bad thing.
But ofc this is a general thing and I don't say pestering chat-bubbles are tricking us to buy something. No the overall trend with big data and instant gratifications, without boundaries is my issue.
I think we adjust to the new reality of this medium, we have social rules governing our society these laws of interaction should to some degree be reflected in this free space.
Anyhow ;D .... already a way to long an complicated reply