Tagging @Kevin Bendixen , @Milan and @Nathan Sudds in case they can help 

@Ben Williams Oh wow, I don’t envy you on that one!  I wonder if using something like PDF.ai would be useful in that you could chat to the document and have AI create specific articles -- not sure if it would be able to output code you could use in the Intercom Articles view but now I’m very curious!

Another option that I’ve used many times to put together step by step instructions is Tango.us -- it’s very convenient for putting together the steps and has a number of different output formats, I think there should be at least one that could work well for this type of content transfer to Intercom.  

But I think 200 pages of PDF support content are going to be a bit of work no matter what method you use but hopefully one of these ideas might be helpful.   

If you want to use the content as is, then maybe some sort of tool that does PDF to HTML, Markdown or something like this could work as well.  One of the big challenges will be how that PDF was created, is all the text and image content accessible or do you need to OCR it because it’s just a flattened pdf, etc. 

Last but not least, you could potentially look on Fiverr, Upwork or some other contract hiring site for someone who can work their magic on this and get it converted to a format you could use easily with Intercom as well.  It’s an often forgot about option but your time and efforts might be better applied somewhere else and outsourcing this task could be a great decision. 

I would try some experiments to see what works, if you want help exploring your options feel free to reach out. 

Hope this is helpful!

I have worked out a good option for this, if anyone is interested in how I solved this….

Confluence has a really cool integration with Zendesk so I setup Zendesk with a single user and configured API integration to pull all of the Confluence content into the Zendesk Help Centre.  This is really good because the content is rich content and this is all preserved.  

I then setup Intercom to use the beta feature within Intercom that allows Zendesk content to used as an external source alongside the inbuilt articles feature.

This lets me leverage Confluence content that is always being updated as a single source of truth with the benefits of Intercom’s knowledge bot capabilities.