As someone who works in IT (System Administrator), the oldest OS your machines should have in an enterprise environment at this point is Windows 7. And thats end of life as well, really you should have upgraded to Windows 10 by now or at least be in the process of doing so.
In 2020, if the prospective company I was interviewing with had a lot of machines running Windows XP, I'd consider that a serious red flag. It's a clear sign the company doesnt give a fuck about it's IT backbone/security.
It's ridiculous how some CEOs actually dont think IT is a super integral part of their business. If the business' tech infrastructure and backbone is underfunded, not secure, or ignored, the company will always suffer in one way or another - ways they dont see until its impacting them. Too many older people who own businesses dont understand this and it drives me nuts.
Because of this shit, people who work in IT get put in positions where they're overworked, and they dont have time to implement true quality of life changes. You cant stop doing repetitive tasks that could be resolved if you spent the time to automate them because your bandwidth is too small for what the company is allowing, and they dont pay you enough to really go over and above and fix things on your own time.
/rant (but relevant)