Sorry. You didn't explain very clearly what you want to do. There is a Trimble Connect Sync app that can be used to bulk upload files to your Trimble Connect storage. I'm not sure if it's available for non-paying users but you could look into it.
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You can also go to your Trimble Connect storage in your browser and then drag and drop files from the folder on your computer where you keep them. As a SketchUp Free user you get 10 Gb of storage.