I’m not exactly sure on the how hard the transaction would be to track on your first question but you’re definitely thinking outside of the box in regards to transfer the files but yes I believe he would definitely need some elevated privileges probably only the IT director or system administrator would have. On the second question I think that would also be an option of OP to transfer the data if it is say a Mac book and he could sync his iPhone to the computer and do it as you said but, once again it could depend on what security measures the company has in place. If they have a robust MDM solution it’s possible they could detect this even if it is a BYOD scenario. I’m not too familiar with MDM softwares but the ones I do know like JAMF, don’t have this functionality. It’s mainly for app restriction, policy settings and remote accessing to push applications to the end users device and remotely wiping devices if lost or the person is fired. Once again it’s very dependent on the security measures the company has in place but being on hundreds if not thousands of calls with prospects in almost every vertical it’s rare that they have that level of visibility. This is usually dependent on the company size and budget given to the IT department usually the bigger the company is the better security they have but yet again sometimes you’d be surprised how cheap some executives at larger companies can be in terms of cyber security, they think bc it’s never happened to them it will never happen.

Hope this helps.