Micromanagement of KPIs from top to bottom of the sales org. If they could have you work 100+ hours/week, they would. The stress level at Datadog couldn't be higher as managers are constantly looking for updates on anything and everything they can track. Tons of busy work that eats up hours that are not necessary to doing your job well.
All management seems to care about is PG, PG, PG (pipeline generation). You'll feel more like a BDR than you will like an AE. Also, BDRs do not contribute a lot to your prospecting either so it's all on you. Datadog prospective accounts are so over worked that many of them have also blocked Datadog's email alias making it increasingly difficult to get a hold of anyone.
Even though deal cycles are extremely long, the business is still managed on a weekly and monthly basis which only adds to the stress levels across the sales org. While many of the managers are former reps, it's as though they've completely forgotten how much time and effort it takes to close a deal there.
Pay is below market average. Datadog knows this and doesn't seem to care as they have gotten that feedback a number of times from reps who have left.