That's true - we're a small (15 person) team & I lead Design & Product so the CEO is my "direct report". However, just because you have a lower likelihood of s

That's true - we're a small (15 person) team & I lead Design & Product so the CEO is my "direct report". However, just because you have a lower likelihood of success, it doesn't mean you shouldn't ask. If you receive a 'No', it will probably speed up the inevitable decision of whether you actually want to stay with this company (knowing that they aren't going to incentivise your performance). I would also keep in mind that you should only be asking if you either feel you're being paid lower than market or that you've taken on more responsibility so now your wage doesn't adequately match your role. Just asking periodically without a reason isn't going to work for anyone.