Great potential but very disappointed - Enterprise Account Executive Datadog Employee Review

2.0
19 Mar 2024
Recommend
CEO approval
Business outlook

Pros

Well known brand in the observability space with a robust platform of tools The opportunity to work with a group of very smart people. Especially across the Product and Sales Engineering orgs. Both groups were essential parts of the enterprise sales motion Extra benefits like the fitness reimbursement and maternity leave which pays out a percentage of commissions while on leave. They also offered fertility assistance. Catered lunch 3x a week Generous 3 quarter ramp period

Cons

Pay - leadership from the c-suite to sales have the mindset “it sells itself” which explains the below market-value salary for the expectations Enjoy the ramp/MBO bonus while it lasts because the majority of the sales org was far below quota. Enterprise, mid-market and commercial included. It wasn’t uncommon for those who do close deals to have their commissions retroactively restructured to benefit the company and keep reps around for long lock up periods…golden handcuffs. Complicated pricing that frustrates customers Some pockets of great ICs turned leaders but mostly a boys club of sycophants who were self serving and dishonest. Constantly changing goals and arbitrary KPIs that did little to increase billings but packed calendars with ineffective internal meetings to justify the bloated middle management structure. Mandatory 3-day RTO. There are not enough desks to support the current sales org so good luck fighting for desks or phone booths. Otherwise you can take calls from the cafe where they serve free lunch!

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Datadog Response
2y
Thank you for sharing your insights and experiences - we're glad that there was so much that you enjoyed about Datadog. We also take your feedback seriously and acknowledge that there are areas where we can continue to improve. We understand your concerns regarding compensation and the challenges faced within the sales organization. We continuously review our pay and compensation structures to ensure they are fair and competitive within the market. As we scale as an organization, we will also continue to explore and invest in sales tools. We remain dedicated to creating an environment that fosters growth and success for all employees. Thank you again for your feedback. Your input helps us grow and better serve our employees and customers alike, and we appreciate the impact you had while at Datadog.

Explore other reviews about Datadog

5.0
9 Jun 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
18 May 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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