Pros
There's a lot that Datadog is doing right: a product that customers love; strong brand (marketing, content, events are all high quality); smart, kind employees; transparent; making investments in people (manager training has been going on for the past year, Udemy); benefits are very strong - among the best you'll find; a culture that respects life outside work.
Kontras
As with any company that is growing at the rate that we are, there are definitely some things that either break or that are needed which aren't in place yet. There has been a significant investment in scaling up the People Operations function (which used to be almost entirely recruiting), so now there are HR resources for employees and managers. We continue to have a lot of inexperienced managers, but as mentioned above, the company is getting them training.