I've dipped on job prospects which involved code challenges that require me to get their codebase working on my machine. I inevitably wind up having to troubleshoot their broken setup and that takes way more time than doing the actual challenge.
Ruby desperately needs innovation in this space. Bundler and rbenv / chruby / rvm just isn't good enough. Vagrant / Chef just isn't good enough. I understand that dependency management is a hard problem, but other languages aren't half the headache that Ruby is.