Pros
There are some very smart people working on the data science team at Root. Oh, and there's "free" lunch.
Cons
There is little to no cohesive data science "team" environment; I had taken the job hoping to collaborate with all of the smart people around me, and instead was thrown onto an island all by myself with nothing but a laptop and a smoking hot mess of unintelligible data with no documentation. Typical startup culture, but inexcusable nonetheless. The management, or lack thereof, is appalling. I was encouraged to take hacky shortcuts regularly in my work, but if I had suggested such practices during the 8 hours of interview examination, I'm not so sure I would have been offered the position in the first place. Everything in the name of time! If you're interested in cooking up lots of quarter pounders as fast as you can, then this is your place. If you've done a graduate degree in a technical field and are eager to produce quality, thorough results, I would suggest looking elsewhere. And I would also recommend, if you can help it, adopting the male gender prior to your employment start, as your credibility will likely be in constant question should you identify as a female.