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.).
The job I want is one that is often filled internally.
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."
There might be another side on this. There might be a decent manager who knows that the current employees don't have the skills to do the job. Being 5-10 years in the company does not necessarily mean you are a good leader or manager to be promoted and become team lead, VP of engineering or CTO. Companies do that same mistake all the time.
Yes, it works well at the lower levels, but this strategy falls apart if you want to work your way into the upper levels of an established company. These companies want someone who has proven that they can deliver results within the company, understands how the company operates, has built enough relationships within the company to have sufficient influence, and isn't going to establish a team and then leave for another job in a few years.
This true; at least in the US; where I am - in my experience. If you are at Sr. Manager or Director level (leading group of 10+ HR reporting to you or cross functional team lead), it gets increasingly difficult to change jobs frequently.
