Hi! It's nice to hear from someone with an interest in this.
The Jenkins stuff is all AWS and Chef based and the whole thing is documented, including requirements motivating the design, at
https://github.com/scala/scala-jenkins-infra/blob/master/doc/overview.md. (A lot of the documentation is new, written by me in the last few months, based on Adriaan's notes. I'd be happy to improve anything that's unclear, on request.)
A bot called Scabot triggers Jenkins jobs for incoming pull requests on GitHub.
There are a bunch of open issues on this stuff at
https://github.com/scala/scala-jenkins-infra/issues and
https://github.com/scala/scabot/issues (some of them a bit out of date or not very well explained, since it's usually been just 1 or 2 of us working on this stuff, but we can improve any given ticket on request). Most of the tickets were opened in a Scala context but would probably apply in a Dotty context as well (at least eventually if not right now).
I'm just a spectator on Dotty, unless something in the CI breaks :-), so perhaps the Dotty folks could comment on what kind of help they might be able to use here. And/or, you might just look through the open issues and see what interests you.