Pros
The product is very good, and it demos well to customers. Competitors are beginning to catch up, but DataRobot still has some compelling differentiation. The company is very focused on making customers successful, sometimes to the extent of providing training and professional services at no cost.
Cons
This is the worst-run company I've ever worked for. The culture is toxic, the organizational structure makes no sense, the go-to-market model is a disaster, and the company lurches from one initiative or strategy to the next. The CEO is a mercurial data scientist with a massive ego who is in way over his head trying to run a company of this size and complexity. He and his small inner circle of inexperienced - and often junior - employees make many of the decisions, often leaving senior executives out of the loop. The company has recently brought on an experienced president/COO, but time will tell whether he is truly empowered to make the changes that need to be made.