He was not screwed. He was contractor and contractors typically do not get any options at all. After one year, GitLab offered him options as an incentive or bonus with standard four year vesting - similar to how big companies award you stock options/RSUs annually.
Well, he is under the impression he was a 9th employee and the grant was delayed. So if this is a bonus for time served then it wasn't made clear to him what's his standing. It doesn't even make sense to award options at that point unless they are backdated maybe [1]. And I am willing to bet money that the nature of the options was misrepresented. Foreign contractors are particularly vulnerable since they wouldn't have experience with US law and finance.
I don't know of any companies that award options yearly/bonus, it would be an incredibly stupid thing to do, must always do RSUs [1]. Options may be adjusted for dilution or promotions yearly, but that's different. Options are designed as a tool to get a % proportional to what you add as value. If you get options with your own work valued in the strike price, those options are orders of magnitude less valuable than the options you get at sign up. If gitlab made that clear and he agreed, then I agree gitlab are in the right, otherwise yes he got screwed over big time.
[1] The problem with delayed or yearly options grants is that workers have a huge incentive now to lower the strike price for the next valuation. Why would you work hard against yourself if you are really just increasing the price you buy at? You'd be much better off to work against the company at this point and score a lower strike price. Further how can you trust a company that makes you work against your own interest. Perfect example of lose-lose.
