Talk to JC user "dasleben." I believe he went straight to the right seat of a 757 from flying 402s at 9K (Cape Air).
The thing you'll find at 9K is an odd mix in the pilot group. Since we operate as a Part 135 commuter, the age 65 rule does not apply and there are some retired airline pilots who came here because they can no longer do the heavy jet thing due to their age, but want to keep flying.
There are also a surprising number of career pilots here...the top 25% of our seniority list (44 of 230) have been with the company for ten years or more. Usually those guys have good pay, awesome schedules, are home every night, and see no reason to move on. They also have unbelievable job security. Depending on your personal life and future goals, it's hard to put a price on those characteristics.
The bottom half of the seniority list (about 120 or so) have been with the company for two years or less. So there is this big gap between pilots coming just to get their time and get out, versus those who intend to stick around long term. You'll rapidly advance through the ranks your first two years here, then hit a brick wall as far as seniority goes.
I've only been here for a few months, but from what I've seen, very, very few pilots have any interest in going to a regional jet job. They might not know what they want to do next, but it sure as heck doesn't involve sitting in the cockpit of an RJ ;-) That's certainly the spot I'm in.
It's just the type of personality 9K attracts. We don't generally chase after the stereotypical airline dream. I know several pilots who came here from flying the bush in Alaska, one guy with 6000 hours of time flying pipeline patrol/skydiving, etc.
I think a fair number of pilots leave here to fly for charter or corporate gigs--but that might be more a function of their personality than qualifications.
One thing is certain...flying at 9K will never *hurt* your career. It checks a lot of boxes like multi, PIC, 135, IFR, airline time, etc. You'll become friends with a lot of people who can probably help you in the future. You might be surprised where it will lead.
Good luck if you decide you want to come here!