Thanks for the reply @lewtun. I’ve never heard of a retriever before, and will do some digging on the resources you have shared.
My main concern is that most of the answers would be specific to that developer product, i.e. only found in product developer docs and discord/slack chat history. The answers are in the chat history (which I have), but I haven’t found an efficient way to identify answers or create question-answer pairs yet. I realize that may be less of an NLP problem but more of a matching algorithm or manual labelling for a different classification model. Another approach is trying named entity recognition and trying to find Q&A pairs through that. Any suggestions anyone may have on that are welcome too.