Pros
The people -- who are suffering under oppressive leadership that uses smoke and mirrors to keep them in line. The people of color particularly are some of the few bright spots of this company, but most have been driven out and you most definitely won't find any in upper management.
Cons
You should be very diligent about what you take for fact on this site. Lemonade has actively been ignoring Glassdoor reviews, saying they don't hold weight because they are only from people on the lowest rung of their ladder. That's something you have to be really careful about at Lemonade -- they hide the truth behind their fanatics within the company. You can never take any of what is said at face value, because it's almost always a shiny surface on a much darker concern. I encourage anyone reading these and considering working here to really examine who is leaving 5-star reviews. When it's only people on the director/manager level, while everyone else is clearly miserable, that's a massive red flag that shows what they truly think about people they deem to be lesser. Shai and Daniel in particular are some of the biggest offenders. They constantly maintain an "everything is fine" demeanor while the inside is burning and stock prices are plummeting to a point where they aren't even a worthwhile point of compensation. They meddle in things they don't understand and focus on petty mistakes instead of wide-sweeping, systemic problems. Everything they do is to look good on the outside, no matter the cost. I could go on and on about the smoke in mirrors -- like how they claim to be progressive, but viciously shut down Black employees who speak out, consistently dead name people while ignoring all efforts towards a fix and have no consideration for the poor who they were originally marketing to -- but at the end of the day, this company won't change because the people running the show will never look critically enough to understand they are the ones who have caused this downfall, and that makes me sad for the wondrous people that have still clung on to the hope that the company initially gave. You'll find some of the best souls in the world here but they're being exploited, demeaned and diminished by power structures that need to be broken down, but will likely never will.
