What Windows keeps about USBWindows logs all memory sticks and portable disks inserted into the computer, including serial numbers and how long each stayed connected. One that turns up for the first time at two on a Sunday morning, a few days before a resignation, needs an explanation.
Cloud drives and webmailWhichever tool it was (OneDrive, Dropbox, Google Drive or webmail within a browser), it leaves traces on the machine: sync databases, cached tokens, history, and any uploads that failed midway. After signing out and tidying up, almost all of those traces will remain.
Wiping tools and mass deletionDestroying evidence is generally a good way to create more of it. What is left includes the name of the tool, when it was run, and (often the detail that decides things) everything the tool never got to.
The sequence is the evidenceEach of these may arrive with an innocent explanation. Place the events in order against the clock (files collected, stick plugged in, upload completed, wiper run) and it becomes much harder to call it coincidence.