I was at a company once where I had a direct line to the CEO, we would meet 1-1 a few times a year, and he consistently encouraged me to "push from the bottom" for change.

Between the CEO and I were an incompetent manager, a very incompetent director, and a very sharp President who preferred the status quo.

In hindsight, that the CEO was encouraging me to basically undermine my manager showed a chaotic and unspoken power dynamic that I wasn't mature enough at the time to understand. What followed was a frustrating 2 years of trying to show a manager who was being managed by his team that our tiny 80 person company wasn't Google scale, didn't need to be Google scale, and that we were wasting 75% of our development efforts gold plating everything for no reason.

What I should have done, almost immediately, was either shut up and collected a paycheck or moved on to brighter and better things (which is what I eventually did).

The org chart is the org chart. You can communicate information upwards, but you can't communicate action upwards.