AI Platform builds the foundations of Datadog's AI efforts. The org is 70+ people organised in three pillars: training and serving (GPU clusters, distributed training, low-level infrastructure), agents (agent harnesses, memory systems, the internal AI gateway that routes every LLM request at Datadog), and evaluation and experimentation. This role sits in the evaluation and experimentation pillar, which owns Datadog's shared annotation and evaluation infrastructure — including the evaluation scenario store and the telemetry archival systems used across the Bits org. Together they let an agent travel back in time and query what Datadog looked like at the exact moment an incident happened, so scenarios can be replayed and agent performance tracked over time.
Specifically, you'll be the first applied scientist on GenSim (Generative Simulations), the team that builds the environments Datadog's agents learn in. GenSim doesn't replay sampled telemetry — it stands up real, fully instrumented applications that talk to Datadog, drives them with representative traffic, injects controlled failures, and records what happens. Because GenSim injected the failure, it knows the ground truth. That corpus — hundreds of postmortem-derived scenarios and thousands of runnable applications — is today the primary source of post-training data for Datadog's own SRE model, and the substrate that Bits AI SRE and our other agents are trained and evaluated against.
The team has no applied science support today and is learning post-training data methodology on the fly. That's the gap this role fills, and the open questions are the interesting part. How do you tell whether a generated environment is actually representative of the messy, incomplete telemetry real customers run — rather than a suspiciously clean one where every monitor exists and every service emits complete logs? How do you make injected problems genuinely hard, and how do you even measure difficulty? How do you define and control the quality of post-training data when correctness, representativeness and difficulty pull in different directions? How do you evaluate an agent end to end when the trajectory is non-deterministic? Creating simulated agent environments for monitoring and SRE work is not well solved in open source or in published research, and Datadog is the leading company in this field. If those are the problems you want to spend your time on, come build this with us.
Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.
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About Datadog:
Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.
Equal Opportunity at Datadog:
Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.
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