HR depts hire these companies that break out the digital proctoscope, and they do things like find your social media accounts. Also, if you piss someone off, they can rat you, and you can be fired with cause.
As I've said, I've personally seen a lot of felons do fine.
"Being upfront" doesn't mean immediately stating it up front, but it also means not lying or pretending it won't come up. Also, there are time limits on this kind of thing.
I know a chap that graduated from Brown, in finance, and got busted in college, with misdemeanor pot, and that haunted him for decades.
I also know a chap that did four bids Upstate, retrained, and got a job as an IT admin for BNL. He did great, but burgers killed him.
Of course lying is a very bad strategy. But so is coming out without being asked IMO.
I have no personal experience just from acquaintances.
I don’t know about time limits I guess that depends on the country. For example in Germany this kind of information is usually not public so you will have a much easier time - also with the penal systems goal to rehabilitate not to punish. Of course it’s still very difficult.