With SketchUp, save the file locally and then save it to TC. After that, during the session when you hit Save it should save to both locations. Being the belt and braces sort, I periodically do a Save as … to save locally, too.
For LayOut there isn’t a way to save files to TC from within LO but you can open the TC interface in your browser and Add them. It would be nice if they would make TC available within LO.