Pros
Maybe I drank the Kool-Aid, but deep down in my heart I still believe that Southwest is a good company. The benefits package is awesome. The company, on a whole, still believes in "feel good company culture" activities. Time on (working a schedule so you have every other Friday off) is definitely appreciated.
Cons
Soooo...yeah, then there's the Technology department. Leadership often does not listen, value, or respect the opinions/ideas/thoughts of the individual contributors on their teams. Leadership often talks about being "transparent", and stresses the value of "communication", but those are just the latest HR buzzwords and there is no true action behind those words. There is definitely a good ole boy network within the management structure in Technology at Southwest, and if you're not "in with the clique", then you're going to have a difficult time. There are a number of highly skilled people within Technology who are seriously being underutilized and overworked. This company is still operating as if it is a small airline, but it's not, so people are working ridiculous hours IN THE OFFICE and the work life balance is quickly flying out of the window. Management does not seem to appreciate the number of hours their staff puts in to ensure stability within Technology. Then you have the "lifers" - those that know that better exists outside of SWA, but they've invested so much time here that it's more beneficial for them to stay until retirement. Couple the rampant politics and selfish leadership with the lack of 21st century "amenities" for technology employees (working remotely, up to date technology, decent pay) and you have a recipe for disaster. It's only a matter of time.