It's an old Unix convention: ^W (Ctrl-w) would remove a word using the Emacs keybindings. So in place of striking out a word, you'd put ^W and the replacement, as you would when typing it out ("clueless...err, no, wait...ctrl-W...HELPFUL").

The parent is using it to mean https://en.wikipedia.org/wiki/Logical_conjunction

^ probably means super-script format in this context.

I'd probably say ~helpful~clueless instead though