This is the real Boiler Room, stay away! - Sales Datadog Employee Review

1.0
Aug 6, 2019
Recommend
CEO approval
Business Outlook

Pros

Great tech for the commercial market

Cons

If you have seen the movie Boiler Room and like it, this is the place for you. Sales leadership is an absolute joke from the twice a month "All Hands Call" where nothing is learned other than who's in the good old boys club to the the weekly Slack asking "who's closing what?" from the CRO. They talk about the rocket ship revenue growth but don't tell you its all in the commercial market. They are not ready for Enterprise sales, ask them to name their top 10 Enterprise customers and the revenue associated with those accounts. It's a 12-18 month sales cycle and they promise a long runway to build your business/funnel but you will be on a performance plan by month 6. Turnover is extremely high...as of today there are 1,263 employees and 701 former employee's according to LinkedIn. If you are applying for a job here, I highly recommend you reach out to get the real story from the person you are replacing.

Explore other reviews about Datadog

5.0
Jun 9, 2026
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

People first culture, endless opportunities to grow, learn new things beyond your role’s scope and get promoted

Cons

Compensation on a lower end

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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