And I have WINE to thank for that layer of compatibility.
If it's important to deploy as a Windows process, then the Windows Linux subsystem is not much better than a VM. Point is, its no substitute for a (better) MSYS2/Cygwin.
Now if you're saying that the webapp itself would be required to be a Windows process, there's really no way around that. But as I implied elsewhere, the biggest stumbler for Rails on Windows has always been the lack of a compiler. Whether you compensate for that by installing a subsystem with that capability or by using a VM with the capability is largely a local problem to the company.
http://www.hanselman.com/blog/DevelopersCanRunBashShellAndUs...
To contrast, Elixir runs on Windows. However, it may be hard to get all your projects up and running due to various baked in concerns where they were written to support Unix-like systems only.