The ability to add a link to documents that have been attached to the record level would make document management much easier when making HubSpot your single source of truth. The ideal functionality would be an additional attachments section at the top of the email creation model. That button would allow a user to add a link to a document in the email similar to how the quotes button works.
This would allow HubSpot users to get one step closer to making HubSpot the single source of truth for their sales and service teams. With any document that has been sent to the user this way, the HubSpoter would gain the ability to see opens of documents, documents that would not make sense to add to the standard sales documents. There is also the other advantage of not stuffing a contact's inbox with attachments and the ability to share larger-sized files.
With CloudFiles you can do something close to this.
It is a widget that appears in your record's sidebar (same place where attachments widget does). It allows you to upload files from a variety of sources including HubSpot's own storage (i.e. the file manager). You will get the file link in record context and can then attach it to emails. This link is trackable and can integrate fiel views with workflows as well.
Link insertion does not appear on top of email creation modal however since external apps cannot have that deep an integration. But it does move things one step closer as you mentioned.
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