Combining Time and Milestone vesting for a CTO – What are some good milestones for a CTO to have to trigger extra equity?

He would be more of a CTO/Co founder hence the slightly larger than usual %. But not that big because I have taken all the risk so far and we are already generating revenue while I've been paying him as a contractor.

I'm currently considering a scenario where:

– He gets 10%, 1 year cliff with 4 year vesting period

AND

– He gets another 5% (which adds the the equity being vested in that remaining year of the above) if the ARR is at a certain level by the end of year 3.

AND/OR

– He gets another another small % if we manage to secure a certain amount of investment within the 4 year time vesting period. But he would need to have made a significant contribution to us being able to get that investment (I don't understand how this would work though if it's more of subjective thing that I decide).

I'd love to hear your thoughts on this, especially from those of you who have been in this situation from the CTO perspective or founder perspective.

Thanks!

submitted by /u/LiquidFootballAha
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