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require with a tilde(~) works because in the CSS files it resolves the path to your node_modules
directory and you don’t have to set up a relative path.
In your case you are currently in the signup directory so you would have to go up 3 directories before you reach the assets directory.
So your relative path would become:
../../../assets/my-img.jpg
With Webpack you also have the option to resolve straight away to a directory with a resolve alias which might be a prettier option for you:
https://webpack.js.org/configuration/resolve/
Hope that helps.
Source:stackexchange.com