What makes you think that the issue Reddit faced today would be fixed by rolling deploys?
Without knowing anything about this particular issue, at a basic level I'd think any non-trivial site should have a system of rolling out changes to a small percentage of servers and have automated monitoring that fires alerts if it notices any disruptions in functionality. If nothing goes wrong then gradually roll out to 100%. If something does then stop the rollout and go back to the last stable version. Then engineers can look at what went wrong.
Autonomy to get things right when it's the right call is sort of a rarity and a real luxury in my experience. I've built a ton of things I knew could have been built better if the rest of the company saw the value in doing so.
When given the option to do your job as asked or quit because you don't have your way, I'd rather just do my job and wait for opportunities to improve things if they present themselves.