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Interesting idea.

Something to dig into more might be the developing PLG software space. This idea is not dissimilar to PLG in general, though I think most PLG cases are for larger implementations. PLG covers a lot more but might be worth diving into a bit.

PLG, Product Led Growth, is similar to your implementation in that you are trying to observe how users, not buyers, are utilizing your software so you can sell/expand to them.

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Hmm so PLG is a space but do you know some implemenations?

These are going to all do a lot more than your tooling but might give you some ideas. The combined theme here is processing the data of your existing users to sell to them.

https://www.salesforce.com/products/genie/overview/ https://www.getcorrelated.com https://www.variance.com

More than just interactive chat but similar on the engagement front.

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