At Admin Panel -> Settings -> Switches, the "bulk submit" switch (currently only in WSN Gallery) allows submitting a bunch of images at once which each become a separate listing. When the switch is on, you can configure the permission by usergroup at Admin Panel -> Members -> Manage Usergroups. You can set the number of images at a time that can be bulk uploaded at Admin Panel -> Listings -> Listing Settings.
To do a bulk submission, simply click the bulk submit link in the actions box on the front page or in a category. The uploads will be processed through the bulk uploader, which will need to be switched on as well. Each listing will be auto-titled based on the file name and will go to the category you've selected.