Pros
There were a lot of good people. Created a very friendly culture that was good to be a part of. The Marketing Team went from being pretty bleak to pretty strong when they brought in new leaders last year. I learned a ton from them! BRAND NEW office in good FiDi location will now have lots and lots of space to spread out in.
Cons
Metromile is a Groundhog's Day of poor decision making. Company continuously made huge plans and then would give up on them when they did not deliver instant results. Not once in my time with the company were we allowed to stick with a plan for one full quarter. Really. There were very few people with insurance industry experience in the company and now they are all gone. The very bloated Product Management team has nobody with industry experience, yet rules the roost. While there are some nice people on that team, none of them have have any idea what they are doing and refuse to take input from anyone else or any other department. The least experienced people in the company get to make the biggest strategic decisions. As a result, the company had multiple plans and strategies that were not at all in synch with each other. Unsurprisingly, the product is pretty poor and generally fails to deliver on expectations. The sign up process is pretty terrible (thus making customer acquisition costs hard to bring down), the devices used to track miles are very expensive and unreliable, and systems were all designed by people who have never spoken with an actual customer. The customer experience is terrible for most, but it isn't sexy, shiny and new to work on that. The finance team is the other powerful department within the organization. It lives in this fantasy land of spreadsheets and has no understanding that the real world doesn't work that way. Expectation was to double growth while halving cost, while providing a massive list of things we were prohibited from doing because loss rates were terrible in the past. (Tough to grow your business when you are only licensed in 8 states and aren't allowed to market in 3.5 of them!) The company recently had a massive layoff, including the entire sales and marketing function, so doesn't seem like there is a much of a plan here (not that there ever was) and can't see a future where this company isn't sold for parts.