Pros
Esri has a cult like following with it's users. They are a pleasure to work with. The message that is given to users is an easy one to speak and the users are loyal. There are a lot of really good people who work for the company.
Cons
The people in the regions are the first line to users, and the regional structure is what keeps Esri afloat. Redlands is out of touch with the users. They have put too many policies in place that they don't understand how it impacts the field people. We never see Jack. You can go 10 plus years without the owner coming around. Make a big sale and you don't get a thank you from the national sales manager, let alone Jack. HR has tried to make Esri into a big company, but they just get in the way. The nickle and dime those of us who are on the road all the time. If you go to a conference and lunch is served, you don't get your lunch per diem, even if you worked through lunch. Coffee and donuts at your hotel? No breakfast per diem. And don't even think about traveling to Redlands and expect to have your own hotel room-- you will have a roomate or pay for your hotel room yourself.