have an applicant who is trying to submit a couple of documents and having trouble

They are trying to submit a passport(with photo) and resume and it is telling them the file is too large. What do I need to tell this person so that it will work?

Perhaps it has exceeded the allocated file size limit of your upload field that's why it is yielding an error. 

I suggest you extend the file size limit of your upload field to it can accommodate larger files.

Guide: https://www.jotform.com/help/33-Changing-the-upload-size-limit

If you have further questions, let us know.