Yes. This would add a lot when you interview for jobs.
End-goal of C-suite at large public companies is very hard, as promotional pathways become more political later on. However, it's less difficult to be C-suite at a smaller company/startup, which is actually a much more unstable job that people taken when they become financially independent and you can exit from VP/executive medical director level (which is typically more stable and pays more).
No. You do not need a full-fledged academic career (i.e. K award, etc) to transition, though if you did, you might start at a higher level. Either do clinical research at residency level or do a research fellowship is more than enough. During training start making some connections and talk to recruiters. These jobs are not very plentiful, but they exist and can be obtained for applicants with the right credentials.
Typically if you don't have a lot of clinical development experience you'd be hired in at the associate medical director level, and will receive training in the first year or two and salary/lifestyle there isn't super fabulous. Once that happens it's a lot easier to find a new job at the medical director, and subsequent senior medical director level. At that point salary growth is much faster.
