I can't speak to insurance, but for 401k: They basically don't. In fact if the company fails fairness testing on the 401k plan, executive contributions to 401

I can't speak to insurance, but for 401k: They basically don't. In fact if the company fails fairness testing on the 401k plan, executive contributions to 401k can be clawed back (actually the bar is much lower - "highly compensated employee" above like $130k. So if Google directly employed all of its contractors, it would likely fail fairness testing on the 415 contributions to after-tax 401k, and all the Software Engineers pushing $70k or whatever a year into their 401k would have half of that disallowed by the government).