Esri created the GIS industry and many of the old timers are stuck in their ways. They don't realize we're living in a completely different digital world than we did even 5-7 years ago. You are kind of thrown in the deep end when you get hired - there isn't a lot of hand-holding and bringing you up to speed, which can be frustrating at times. Most institutional knowledge is not written down or easily found. You have to build your own knowledge base of who knows what, which teams do which things, and so on. There is no functional org chart so you have to figure it out on your own. Jack, the wonderful visionary owner of the company, is getting up there in age and there is no true spiritual successor around for when he departs. He is the captain steering the ship and when he leaves things may get very far off course.