Ime it never hurts to share your thoughts candidly with the leadership as long as your thoughts are what leadership wants to hear
I've had one favorite boss get fired, and at least two leave (forced out/encouraged to go) because they agreed with us but their peers or boss didn't. Agreeing with them is fine until it isn't, and then you're a collaborator.
And then there's agreeing with the VP or CTO, but the people between you don't, and try to suppress your enthusiasm. If you go over their heads it better be to get transferred to another team instead of trying to change things in place, because now you're squeezing them and they will retaliate.
heh, been there. Sometimes I feel sorry for those that high up, especially the ones that DO mostly see the problems but are powerless to do much because of all the shit between them and the solution.
The higher up you go the more power you have but the less control you have. That seems paradoxical but consider the old adage 'if you want something done right, do it yourself'. You may have the power to hire and fire but have little control over the day-to-day decisions that matter.