Interestingly, that might be the case for Fortune 500. But among the fortune 10, most CEOs/C-Suite are engineers with long tenures at the company.
Actually, if you look back at some of the most influential companies in the Valley at their peak, that's been a rule of thumb since the Fairchild days. Andrew Grove is an example of that [0].
Then along came the laser/UPC/computer system and deskilled the job. No longer did you need to know the difference, the computer printed up a natural language description of the item. This allowed stores to get much larger, because no one could know all the prices in a large store (early department stores handled the size by making you pay for items in each department, using store balance accounts to not create too much friction). This fundamentally reshaped the relationship between capital (who owned the stores and the computer system) and labor. It's actually the exact same alienation of the individual from their labor that Marx was writing about in the 1850's, just for jobs that didn't get the same attention.
Similarly, an in-law worked as a teller at a bank. 50 years ago that job would have more upward mobility because banks managed their risk locally: after many years as a teller and then as a loan officer you could move up to be the local person making the decision on loans. Nowadays large banks have centralized that with fancy computer systems to guide the decision, so there are entire paths of advancement that essentially don't exist anymore because computers spit out the answer. There is only shift and then branch manager, with once again the owners of the computer system using it to de-skill jobs and cut off promotion opportunities. (See, e.g. Better.com, using poorly paid contractors to do all the tedious stuff that can't be automated, and then letting the computer do all the high skill work.)
This is, by the by, one of the reasons that computer programmers continue to get paid well, because we are enabling capital to de-skill and bifurcate jobs better and better.
Alternatively put, we've commodified human hand eye coordination and basic speech recognition and intent resolution. This view is definitely supported by the current state of the gig economy.
That is, management was declaring that there was no value in experience whatsoever (until you got to management levels, naturally), and that they could replace anyone with a new hire without loss of performance. (After all, the way you got to be a highly paid retail person was to stick around for a long time and be pretty good at your job.) And while most managers in a retail setting aren't quite as obvious about it, that sure seems to be how they feel: employees are completely fungible, and it isn't worth paying them enough to get them to stay.
(Costco is a notable exception in the US: notice how the standard Costco name badge includes their start year on it, that is one of the ways Costco signals that they do value experience. They are also significantly more profitable per sq/ft than Sams Club, their competitor in the warehouse segment operated by Walmart. I strongly suspect that those two facts are related.)
I'd guess a factor in ending this has been the rise or at least growth of an administrative or managerial class in most businesses.
An apprenticeship model lets people grow, and to some extent a similar model used to apply in business, where the executives and managers were all career industry people who started on the shop floor.
The current system is closer to (closer, not the same as) a feudal system where there is a group of nobility that manages a group of serfs, and there is not much movement between the groups, at least at the same company. Admission into the nobility is based on education and other pedigree, and can never really be had by work experience.