Here's my career progression so far:

May 2000 - Graduated UND / May 2000 - FAR 141 Flight School in Major Metro Area, Flight Instructor, 315TT/33ME
August 2000 - Atlantic Coast Airlines, Flight Operations Intern, 562TT/36ME
December 2000 - Atlantic Coast Airlines, CRJ FO, 664TT/57ME
-Furloughed May 2005. Acquired CRJ Type Rating & ATP, 3713TT/3072ME
June 2005, GE Capital Aviation Services, Contract Pilot, 3725TT/3072ME
August 2005, Corporate Gig, regional Fortune 50 subsidiary, CE560 Captain, 3763TT/3103ME
November 2010, Corporate Gig, international Fortune 50 company, CL604 Copilot, 4816TT/4025ME

For my first regional job, I was hired as a bridge intern then "flowed" into a new-hire class with the blessing of the Director of Operations. I'm sure it helped that I worked for him personally for the majority of my 3 month internship and impressed him and the system chief pilot with some of the projects I worked on.

The contract flying was luck and right place/right time- flying the aircraft that had been repo'ed from my former employer to the desert for refurb, then doing MX test flights and delivery flying to their new owners.

The first corporate job was also luck and right place/right time- got it through Climbto350.com. My current gig was an "off the street" application to the parent company of my first corporate gig... knowing the guys and gals in that department certainly helped me get the foot in the door and selected.

I've been very fortunate. The jobs that I wanted, I have been able to interview for, and except for one corporate flying internship that I wasn't offered in college, I've landed all of the other flying jobs that I've had serious interviews for.