Pros
I've really enjoyed working in the engineering/product department. The culture in this department has been a good experience for me, and the leadership in this group has been really supportive in tackling issues impacting day to day life, and in taking on major issues like diversity. The company is transitioning from growth phase to maturity, so there's a lot of development work to do that involves fixing scrappy code that was written in a hurry a few years ago. That's not a diss at the people who wrote it; that's a product of how old this company is, so don't expect this to be like working at a huge, long established company. That said, the company has been around long enough to have fleshed out agile practices, good version control practices, lots of documentation--the sorts of things that start ups tend not to have at all, so I like that it's a solid in-between environment. The engineering and product team is pretty spread out geographically, so everyone comes to NYC twice a year for "Festivus," which involves a hackathon, speakers, lots of food, lots of social events, etc. It was a really fun time. The remote culture in engineering is really strong; because so much of the team is remote, everyone is really good about doing video calls, bantering on slack (the #cats channel is great), and keeping up communication (even informal stuff) without having everyone in the office. I really can't speak to what culture is like in other departments; as a remote employee, I don't really see how that culture plays out in other areas. Growth opportunities in engineering are good; engineering teams all have clear growth charts (one management track, one principal engineer track), so you can see your next few possible promotions and the rubrics for them ahead of time. I've seen lots of promotions since I've been here (in this department), so it's actually happening. Beyond all of that, the perks are good. Unlimited PTO is really great, and at least in my part of the engineering department, getting approved is no problem. Healthcare benefits are great--I was on a high deductible plan before I came here, and I'm actually paying less now for a really good PPO plan. No 401k match, but the 401k plan options are still pretty good. Dental, vision, short and long term disability, FSA for childcare and transit are all also available.
Cons
Some sort of stipend for home office/coworking costs for remote employees would be really nice (the pay raise I took when I started was more than enough to make it worthwhile, but remote work isn't entirely free). It does seem like our CEO is a bit of a butt head, but that doesn't have really any impact on my day to day in the job, and there are other members of the exec group I really respect. Priorities do seem to shift a bit quarter to quarter, but it seems like the product group is doing some work to stabilize that on a day to day basis for engineers. No 401k match.