Vantaggi
The software/technology is pretty impressive, especially if you take it upon yourself to really learn how to use it. There are many resources available if you know where to look, the challenge is figuring out where to look and how to apply it to your job. If you are the type of person who likes to move around every couple of years, Hilton affords you the ability to find a job at your next conquest due to the large network of "Hilton Family Hotels". The standardization of processes and technology also adds to that. You can pretty much pickup and begin working at another Hilton without much challenge. There's also the prestige that comes with working at Hilton, the company has an interesting legacy and history, you'll know that when you think about some of the flagship properties like The Waldorf=Astoria, Hilton Hawaiian Village and The Palmer House Hilton.
Svantaggi
When working at such a large organization, it's easy to come across gaps in communication. I found that on the occasions corporate does in fact communicate relevant information, department heads at the property level do not pass it along to the rest of the staff, resulting in a sense of lack of direction. I'd like to know what direction the company is going in but no one communicates it until something goes terribly wrong. It is a very reactive environment. I can't speak for all of the properties but it seems like the one I work at has a lot of management lacking severely in management skills and leadership skills. There are a few exception of course. Additionally, I have run across more computer illiterate and technology illiterate folks than I ever though existed. Etiquette of all sorts (such as email, professional, phone) doesn't seem to be something Hilton Hotels is concerned with.