[giordanobd]

I get what you're saying—I guess what I'm trying to understand is whether a regular user has an unspoken expectation that browsing or using a web app is "private"--in which case that expectation is already broken most of the times by usage of analytics and, less often by session recording tech--or whether it is like walking in a store: no one is bothering you but you know that there's someone that might be seeing what you are doing, and if you stand in front of an item long enough someone is gonna come over asking if you need any help.

Apps like intercom already allow you to specify "triggers" so that when the user does something you can send them a message. I'm not sure how many people actually realize that it is an automated message.

[maxaf]

Considering how much brouhaha there has been recently in the media (legitimately or not) regarding privacy issues, I doubt anyone expects true privacy when using SaaS products or any old websites these days. There are obviously those people who really care about privacy, however those are a minority and probably aren't worth worrying about in your case.

I think making this work well (assuming underlying tech is solid) is a matter of UX technique. Iterate on a solution that makes the user aware of your support capabilities, then make it easy to summon help. Perhaps it'll be more natural if the user must initiate each support session, i.e. by highlighting a section of their screen and twiddling a control which makes it clear that human help is on the way.