Yes you can upload multiple files at the same time! Tendenci's Files Module has the capability to upload multiple files at the same time. To access this feature simply hover to your websites admin nagivation bar menu under Apps. Apps > Content > File
You'll be taken to the Files Add screenview. Hover over the Files tab and select Add Multiple Files.
Select the files you'd like to upload. When they've been uploaded, you'll see 100% done.
Return to the Files module listing by clicking File List in the Files dropdown. From here you can view, edit or use your newly added files.