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 <i>really</i> care about privacy, however those are a minority and probably aren&#x27;t worth worrying about in your case.<p>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&#x27;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.