Pros
The people at Bentley are, for the most part, very friendly and helpful. Bentley definitely promotes a "family" atmosphere with it's employees, sometimes to its detriment. I found advancement opportunities to be there for those with strong industry backgrounds and ambition (I was promoted 3 times in 7+ years at Bentley). After my first promotion, I found the salary structure to be on par with the rest of the industry, perhaps a small bit lower, but overall a good experience.
Cons
Lots of, long tenured, "deadwood" middle management with little to no specific industry related experience for their positions. Marketing for some industry segments and product lines was literally non existent. Too many man hours lost to laborious process, LONG conference calls, and having "doers" reporting to "deadwood" middle management. In short, the "doer" to "deadwood" ratio was 180 degrees from what it should be in an industry leader. With 4 separate verticals (Civil, Geospatial, Building, Plant), and hundreds of applications/solutions in the overall portfolio, Bentley tends to be a "Jack of all trades, master of none" as it lacks a specific focus. The sales compensation model was confusing to say the least, and was more and more unachievable every sales quarter over 7 years it seemed.