Pros
Incredibly bright people, and as we know, even within the Valley, there is great variance in the average intelligence at a company. PayPal manages to somehow hire the best of the best. The work environment is also a very comfortable environment: people get large cubes, free drinks, free snacks, onsite Starbucks, onsite amenities. HR is running a tight ship when it comes to the benefits program.
Cons
Most of the PayPal's challenges stem from one fundamental problem: the extensive population of inexperienced management. Inexperience comes in two forms: either inexperience in raw years or inexperience in the software industry. Inexperience in years is shown by the fact that there are 2 tracks for management. If you are on the golden boy track, you will hit Director by the time you are 33 or 34, Sr Director by the time you are 36, and are on track to being a VP at the next re-org very soon. Instead, if you are on the forgotten track, you will find yourself pulling 40 or 41 and struggling to get the nod for Director. Inexperience in software is shown by the fact that most of PayPal's management comes from financial services companies like Visa, Amex, and Wells Fargo. The combination of these 2 forms of inexperience drives a highly political culture of territorialism, control, and passive aggression. Products are built and engineers are hired simply to boost the perceived span of control of a particular VP, frequently resulting in VPs being promoted to SVP or even CEO. You can smell the peanut butter dripping from the products. Because of this, the company's success is rarely celebrated, if you are a champion of the customer, you'll be in the world of hurt very quickly, because none of the execs will back you. That said, almost by Darwinian evolution, most of the staff has adapted and evolved into getting their jobs done and satisfying the end customer by ignoring and not being adversely affected by the management.