Install Canto Connect using the installer on this page: (Supports Windows 7, 8 and 10)

Once installed, login using your Canto URL, email address and password:

Click the "Upload to" button and select the folder within your library you would like to upload to:

Click "Add another folder" and select the folder from your computer which contains the assets you would like to upload:

Once the folder has been added, you can click Upload from the bottom left to begin uploading all the assets to Canto:

If you have the Metadata Pop up option enabled for Advanced Uploader/Canto Connect, you will be presented with the screen here to apply metadata to all the files at once:

(Settings > Configuration Options > Upload Settings)

Once you hit Apply, the upload will begin.