The Customer Success org has shifted from strategic and customer-focused to transactional and overly sales-driven. Of the many KPIs CSMs are measured against, only one — tied to month-over-month billings — is actually valued. This particular metric doesn’t reflect actual CS impact or long-term revenue growth. It ignores customer health, retention, or expansion strategy and instead rewards short-term transactions that often have no bearing on sustained success. In many cases, strong CS fundamentals are overlooked in favor of “quick wins” that may even hurt customer relationships long term.
Leadership at the top has become increasingly toxic. The company’s COO is now deeply involved in the day-to-day operations of the CS org — an unusual and destabilizing move for a company of this scale. With little CS expertise, his direct influence has led to confusion, the replacement or exit of nearly all directors, and an environment of fear-based decision-making.
Promotions are extremely delayed and largely meaningless. Even high performers wait far too long for title changes, and when they do arrive, the compensation increase is minimal and disconnected from role expectations. Not even mentioning how you will often find yourself competing with external hires for promotions.
HR consistently defaults to what’s written in the policy handbook, rather than applying logic or judgment to support internal movement or employee growth. They often prioritize rigid rules over what actually makes sense for people or the business long term.
The “hybrid” work model is rigid and punitive. Office attendance is IP-tracked, and if you're sick or out for any reason, you're expected to make up that day — no exceptions, no flexibility. This kind of inflexible, surveillance-based approach erodes trust and adds unnecessary stress.
What was once a mission-driven and collaborative CS org is quickly becoming a churn-and-burn environment, driven by misaligned KPIs, micromanagement, and a total disconnect between ICs and executive leadership. You can just feel it in the day to day culture as well, employees are drained and for good reason.
I truly worry if you come to Datadog, you may leave a worse CSM (you might leave as a better AE) than when you started. I hate to say that as this org had (and has) so much potential but ultimately it seems they are just blindly headed in the wrong direction.
