Ask HN: Additional options awarded after vesting cliff – new cliff necessary?
I have worked at a startup a little over a year. My options package included the typical 1 year cliff, 4 year vest. I recently hit my one year vesting cliff. I am in the process of negotiating for more options. Assuming I am given more options, what does a typical vesting agreement look like in this case? Will I have a new set of options with a second vesting cliff one year from now, while the original set continues to vest at its predefined rate? Or can I negotiate rolling the new options into the same vesting package, so they vest at a constant rate and skip the cliff?
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After the initial package with the standard vesting schedule, everything else is flexible and at the discretion of management (almost always the C-suite and Board of Directors). You can try to negotiate and it may work depending on the company policies and the stage of the company. Some more established startups will have a defined policy for this to make everything uniform among employees while young companies are super flexible.