If you were to study this for corporate standardized careers, how would you go about getting data?

I can't think of a reliable, detailed, readily available source of info like that. Maybe LinkedIn for profiles that explicitly state education years (HS and B.S. to estimate age) and then somehow filter through and classify job titles?

Several issues not including users who state themselves "Founder", "CEO", for MLM schemes. Maybe you could cut the population down to users who have had software titles.