Vantaggi
Datadog is a fantastic place to work, where the people are great, the benefits are better, and the management actually cares about you. The unlimited vacation is real and not just a trap to weed out people who take it. Free lunches are fantastic, and the office kitchen is always well-stocked with snacks. The company's growing really fast, and every day you hear about another big name customer. If feels like you're part of something that soon everyone in the industry is going to know about. Imagine how cool it sounds to tell another engineer that you work for Github. That's what Datadog feels like it's going to be one day.
Svantaggi
Several parts of the codebase are currently a mess. Depending on what team you're on, your day to day work might consist of putting out technical fires that have been building up almost since the company was founded and the first lines of code were written. There's very little culture of documentation, and not a lot of urgency to do anything about that. Different teams seem to be split up along lines that may have made sense once but don't anymore, which gets frustrating when suddenly your work is breaking somebody else's. Collaboration across teams is scattered and haphazard.