A warning about cliff vesting
kevin.isKeep in mind that this is written from the point of view of the employee and not the founder(s).
The reality is that it takes longer than a 30-minute interview to determine whether or not someone deserves a chunk of the company that you have devoted your life towards. If a potential hire demanded that I "avoid cliff vesting" (as suggested in this article), I would feel very uncomfortable.
That being said, I think a one-year cliff is excessive. I've found a three- or six-month cliff to be mutually agreeable for both parties.
My take on it, if the guy hiring you thinks about the vesting cliff as a big 'Undo' button, you don't want to work there.
Yup, if your biggest fear is about the people you're working with, you're in the wrong place. I'd hope that most people are better off worrying about whether all those stock options are going to be worth anything at all.
The hard part is, how do you know your founder is good to her word? A year of work, and you get nothing. That is a huge risk.