That goes one step beyond the standard cliff period for vesting. Honestly it doesn't seem like the incentives are aligned: if you make it past a one year cliff

That goes one step beyond the standard cliff period for vesting. Honestly it doesn't seem like the incentives are aligned: if you make it past a one year cliff, your shares / options are vested and they are yours to keep / exercise. You earned them! As other commentars noted, in this scenario you may want to quit but choose to stay until the 24 month mark (bad). The founders may want you to leave but instead of firing you they'll make you miserable so you quit and this portion of the contract goes into effect (bad). My rec: If everything else is solid and there's a cliff period setup in another portion of the contract, get this removed. If there isn't a cliff, convert this to a standard 1, 1.5, or 2 year clif using the normal language (no shares vested until the cliff, then they're yours after that).