Pros
Most of the non-leadership and middle management employees are extremely pleasant to work with. Driven, knowledgeable, supportive and friendly, even on days when slammed with work and angry customers. Customer success especially keeps up an impressively good attitude. You are able to mostly leave work at work once you clock out. No one asks you for a doctor's note for a sick day or anything, which is nice.
Cons
Very little security: there are many days where you find out someone has been laid off with no warning in the general slack channel. Big changes tend to be implemented without being fully thought through and with very little warning. Positions are changed and/or eliminated without thinking about long term ramifications for the rest of the team. Upper management does not communicate much at all outside of sparse town halls. Compensation isn't exactly competitive for the amount of work at a job located in downtown Chicago. I also personally did not have any kind of raise for over 2 years, despite exceeding expectations in multiple reviews. Employees were also told we would get raises this year, only to be told months later after performance reviews were completed that we would no linger be getting them. Not a lot of opportunities for growth if you don't want to be a team lead. Not horrible in terms of holidays and PTO, but not exactly great either.