For anyone thinking Ruby is dying or slow, it's not the reason people like me used it and sticked with it in first place! It's about the experience when you write the code itself. It's natural, like a flow of water, and you're suddenly in Zen mode, where your thought just naturally flow without even you're aware or not. I first time learn Ruby from zero to "hero" in production confidently is in just under a week. And…
The main issue I have with Ruby / Python is the fact that it's duck typed, it makes the maintenance and refactor pretty hazardous. You get objects you don't know what's in there, 6 month later someone changed it, no compile error but it will break when you run it. And so to overcome those major issues they added really ugly stuff that is not core to the language, linters, annotations etc ...
If you have a preexisting codebase I believe the way you can convert it is to add the types that you know on commits and eventually you will have enough types that adding the missing ones should be easy. For the missing ones Any is a good choice.
https://pyre-check.org and https://github.com/python/mypy are popular.