I feel it gets harder at higher levels where companies prefer to promote internally and/or want previous experience at that level (ie: lead a cross-functional project with 20+ engineers, etc.).
For years I'd take a lesser title and then work my way into that position, but any time that doesn't happen, you're stuck not being where you want to be.
When they don't fill that position internally, the first question is, "why are none of their people up to the task? What sort of dysfunction will I be walking into at this place?"
It's sort of a weird, sideways version of "I wouldn't want join any club that would have me as a member."