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I have all of the achievements except that one too.
🔶 UPDATE:
I learned I can fire employees. So in my completed game, I fired my most recent employee and waited for about 2 years but still never got him.
So... I went back to my previous saves. I found my last Montreal save and loaded that up. I again fired the most recent hire and waited for about 2 years and never saw him. Eventually I hired someone so I could re-progress to San Francisco. Once there, he was my second hire. 🎉 100% Achievements Earned!
Maybe my winning save was bugged, or very bad RNG luck for me; but I suspect he was coded to be an early hire in SF. 🤷♂️