The CEO and COO cashing out 500,000 shares each sounds like some kind of prisoners dilemma. What do you do with your shares if you’re an employee at this point? I’d dump half I guess and cross my fingers.
Employees and everyone else are bag holders. This was just a way for executives to get paid. I give it 2 years before Reddit is acquired by Microsoft or someone who wants to use it as a repository of training data.
Employees should always sell their shares as soon as they are able. Not a dilemma at all. There's no point in concentrating your risk in a company you already rely on for your regular pay.