Pros
Engineers are treated pretty well at Datadog. Pay is competitive. The New York office is big and pretty. It's open plan, but the problems with that are mitigated by our culture of mostly talking on Slack instead of out loud (a habit we adopted when our old office reflected sound like a concert hall), so it's not difficult to focus. The work you're doing is rarely boring, because every part of the product is pretty complex.
Cons
You're treated well as long as you're shipping fast. We used to have a culture of soft deadlines, but that's disappearing. The problem is, we're not ready for it to disappear, because for the last several years we've had a culture of not caring very much about technical debt, and now it's coming back to bite us with outages happening left and right, new features being blocked by old undocumented code being impossible to work with, and different teams coming up with multiple bespoke solutions to the same problem because nobody has breathing room to figure out how to work together. Managers will discourage you from fixing problems before a customer complains. We tried to solve this by experimenting with 20% unstructured time, but after about a month or two managers started discouraging people from doing things that weren't directly related to shipping their current project. Unrelated to the growth problems, but here's another issue. When people on my team made mistakes, my manager would use this tactic of saying that he was concerned with "what other people on the team think about you." At one point he seemed to make up that somebody had complained about one of their fellow team members, when in fact we're all pretty sure no one had. I'm not sure if other managers use these kinds of manipulative tactics, but there's at least one. I'm afraid to go to HR about it, since it's gross but not strictly illegal. It's against company policy to retaliate for that, but performance standards are so loose I feel like they'd have no problem coming up with an excuse. Ultimately lurking under the bright and sunny surface of this company is a culture of dissatisfaction at best and paranoia at worst. Work here if you want to get paid well, not if you want to feel good about the code you write. What upsets me the most is that I don't even think these problems are going to affect the company's bottom line, because at the end of the day we're still better than all of our competitors and have a pretty untouchable revenue stream.
