Personal liability (piercing the corporate shield) is a really tough nut to crack. That'd also do some outsized harm- think kids college fund raided for settlement money.
That said, I'd be happy to make it a personal crime to, with knowledge of the law, instruct any worker to use a machine without safety equipment and water hookup, or to work without a mask. THAT should be a personal crime, like criminal charges. And you should have to, when hired for any such supervisory position, sign a one-piece thing that has that law laid out so you can't claim you didn't know the law.

As a manager of blue collar workers that actually gives a shit about my teams this is the answer unfortunately. Many managers don’t care but will if they’re personally liable.

Set up a monitored tip line where supervisors can tell the govt that management isn't giving them the proper PPE to protect their workers. That way if management isn't giving them PPE, supervisors have a place to go turn to instead of being squeezed from both ends. Get an OSHA inspector out on a surprise trip and get upper management fined.

Supervisors need to care about their direct reports first and foremost, over any company demands. One of the best supervisors I've ever had gave me therapist recommendations when I mentioned having a tough time with mental health, and she told me she sometimes took personal days for her own mental health. Another supervisor, when I was going through an even more rough period of mental health, told me that his wife had bipolar and they put a lot of time and effort in, together, for her to feel alright.

I felt like I had those guys in my corner, and I knew that if push came to shove, they'd have my back. They may have ultimately been powerless to internal HR policies, but they reaffirmed to me that my health should be my top priority and I needed to put it first.

That's what it means to have a workplace as a family. The leader truly cares about everyone on the team and has their back.

Well, in this case I'd say split the difference and make it each incident escalates where an incident #1 = "we caught you, we told you", incident #2 = "we told you yesterday to fix your shit / don't do it again, 2x fine" rinse repeat. Otherwise you run the risk of bankrupting a small business that had all 10 of their workers in violation, and maybe even not making a dent in a large business that only had 1 out of 1000 workers caught in violation

In addition to per-incident escalation, what I could get on board with are scaled fines based on contract / business size. The first incident is still "survivable" for small businesses but will actually have teeth for those larger ones. And then of course if they keep violating, say bye-bye economic viability.

I agree very much. I think on the low end fines should go down to be survivable for a small business, and we don't need to fine a big company $100k because someone took their mask off.
But fines should increase steeply by number of offenses, and multiply if management is willfully refusing to provide a safe working environment (IE doesn't want to pay to have a machine hooked up to water/drain, doesn't want to pay to have filters cleaned, doesn't want to pay for masks / goggles / other PPE, etc).

Yeah, it needs to be a percentage of revenue.