Based on the reviews on this site, as well as conversations I've had with Root employees, it seems as if people really enjoy working for the company. Root's employees have bought in to what the company is selling, so to speak.
However, in order to work there, in order to receive a job offer, you'll need to endure one of the most ridiculous interview processes I have ever seen. The hoops you'll need to jump through may make you re-think your decision to apply in the first place.
Although you may meet all of the job requirements and have all of the skills and abilities, the people at Root are searching for some sort of elusive cultural fit. I suspect that "failed searches" are fairly common.
Based on my experience, the following items may happen to you while interviewing with Root:
If they can find a way to grade or evaluate your professional skills, they'll do it.
You'll have to endure a 30- 45-minute phone interview during which your responses will be openly critiqued, as if you were participating in a interviewing workshop at a career services center.
You'll be asked all of those cliched interview questions that you always hear about, yet didn't think that anyone actually asked anymore. Do you want a career or a job? What is your passion? How do you feel about long hours?
You'll be repeatedly asked (in my case, three times) why you would want to leave your current job and come work for Root.
When it comes time for the face-to-face interviews with Root staff, you may meet your fellow candidates (ie, the competition) during a joint interview session.
Over the course of five hours, you'll meet with seven or eight Root employees, most of whom will ask you the same cliched questions. Most all will mention that the job is hard and the hours are long. Some interviewers will use but a fraction of the allotted time, forcing you to sit and wait until the next interviewer enters the room.