Pros
The company does a great job of marketing. It markets both itself and it's product very well. The product is solid and there is a place for it in the world. There are a few great people at Datadog who really push others to be better and inspire. But only a few. Solid benefits. Lots of perks.
Cons
The company tries so hard to market itself as cool and fun, but remember the cool beer fridge they show you on your way in is only open from 4PM-5:30PM on Fridays. From a sales perspective the company is moving from inbound to outbound, but has vastly overestimated the market size and is hiring reps at a painful rate while shrinking territories, forcing teams to compete against themselves, and asserting that even with over 100 more reps and less of a market that it's all up to sheer will power of the reps to get there and anything else are excuses just like 3 years ago The leaders there came up through seniority not on merit so there's a serious gap that exists between vision and execution. Compensation wise this company falls below the bar for the Boston tech scene and will point to the 3 out of 100+ reps who hit their number as examples of what's possible if you outlast your peers, suck up their top companies, and never let go until they eventually maybe take out a trial and become customers