Pros
Fantastic technology, rigorously focused on core strengths of automated ML, very carefully expanding product line with complementary acquisitions to provide consistent automation across the machine learning life cycle. Insanely smart and capable people. Free meals at major offices. Everyone works hard. CEO and senior leadership are deeply and passionately committed to the company and to a degree their employees.
Cons
Management strategy keeps evolving. Painful layoffs of valuable personnel. Challenges communicating value in marketplace - who is the right target customer? No life balance - if you are in, you are all in. Personnel have varying degrees of external experience and may not have had many years outside of DataRobot. The new leadership comes from a very different company, different products, and a different cultures. Adapting will be a big change. The company is so big it really does need to evolve beyond a startup.