Increasingly smart chatbots are making headway in the simpler robo-advice applications. FP Money reported on a series of bots. These are typically text windows which allow a browser on the site, perhaps using the site's main planning tools to examine the typical retirement issues, to ask questions. The text window, typing of the client, context of the screen and a broad library of answers allows even modest technology to provide a chat-like response. You may have used these and not even realised you are talking to a robot, especially if they are the sort of bot that has a human helping out behind the scenes.
You can tell if you experience something like this: an initial inquiry pulls a fairly chatty response 'hang on, I'll have a look' and then a suggested fix 'does this help...' followed by instructions. If you type something relatively predictable related to the instructions (like, 'where do I type that') then the bot can often respond again. But type a long question, 'no what I wan to know is...' and then you get a pause, this can be because the 'bot has given up, flagged the feed as requiring a human response, and now a human is actually typing the answer.
Why don't we see them in insurance? Don't say this too loud, but insurance is actually more complicated than the linear goal of saving a pot of money for retirement. Although if we bring tax and income generation into the picture it is easy for retirement to get complicated too.