Great tech, great training. However, can be a metrics driven meat grinder - Regional Sales Director Datadog Employee Review

3.0
Jan 27, 2026
Recommend
CEO approval
Business outlook

Pros

Very solid tech that is constantly improving and expanding Excellent onboarding and ongoing training

Cons

Zealous focus on metrics to drive decisions at the leadership and corporate level, even when in direct contrast to common sense assessment of what is happening in the specific local market. Arrogance with the Operations (Deal Desk and Legal) side of the house that can make it challenging to get Enterprise deals done.

Explore other reviews about Datadog

5.0
Jun 16, 2026
Recommend
CEO approval
Business outlook

Pros

Collaborative and positive work culture with high ceiling for growth

Cons

Growing pains transitioning from a grass root sales motion to an Enterprise motion

4.0
May 18, 2026
Recommend
CEO approval
Business outlook

Pros

Datadog has a strong product, smart coworkers, and a fast paced environment that teaches you a lot quickly. I learned a tremendous amount about observability, technical discovery, outbound prospecting, and how modern engineering organizations operate. The company has also gives reps exposure to large accounts and technical conversations early in their careers.

Cons

The ramp for newer AEs can feel steep, especially in a hgihly competitive outbound environment. Success often depends on timing, territory, pipeline momentum, and consistent coaching. There can also be a significant pressure tied to activity metrics and pipeline generations, which may be difficult for reps still developing confidence and process consistency.

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