The way that the content directory is loaded expects Unixy filesystem semantics (e.g. executeableness indicated by a permission bit, / as the path separator, etc). There may be other platform-specific stuff in the codebase too (so far I've only developed/run Operator on macOS and Ubuntu).
I don't think it'll be difficult to make things more portable, but CI should be set up to run checks on multiple platforms so that once things are working they stay working.