Senior Security Engineer, Offensive Security

<p>Here at Datadog, we think about offensive security a little bit differently. We embrace automation and AI to run adversary simulations continuously across a massive cloud-native environment, and we expect our offensive engineers to build the tooling that makes that possible. We're looking for a Senior Security Engineer who can execute sophisticated red team operations, write the code that scales them, and take an AI-first approach to offensive security engineering.</p> <p><em>At Datadog, we place value in our office culture - the relationships and collaboration it builds, and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them.</em></p> <p><strong>What You'll Do:</strong></p> <ul> <li>Plan and execute red team engagements end-to-end, simulating real-world threat actors across cloud infrastructure (AWS, GCP), Kubernetes, CI/CD pipelines, and corporate environments</li> <li>Build and maintain custom offensive tooling, automation frameworks, and engagement infrastructure, treating offensive operations as a software engineering problem</li> <li>Develop custom payloads and evasion capabilities tailored to Datadog's environment and modern defensive controls (EDR, SIEM, network monitoring)</li> <li>Improve the efficiency of offensive operations through thoughtful use of automation and AI, accelerating reconnaissance, vulnerability analysis, and reporting workflows</li> <li>Partner with the Detection &amp; Response team on purple team exercises to validate detection logic, improve alert fidelity, and influence threat models</li> <li>Translate offensive findings into concrete improvements by working directly with defensive security and engineering teams to close gaps</li> </ul> <p><strong>Who You Are:</strong></p> <ul> <li>You have 5+ years of hands-on experience in offensive security (red teaming, penetration testing, or adversary simulation) with a track record of operating against mature, well-defended environments</li> <li>You write production-quality code (Python, Go, or similar), can build your own tools, and automate your workflows rather than relying exclusively on off-the-shelf frameworks</li> <li>You have deep expertise in at least a two of the following areas: macOS security, Linux security, cloud platforms (AWS, GCP, Azure), Kubernetes, or CI/CD pipelines</li> <li>You have experience developing evasion techniques against modern defensive controls and understand how detections work from the blue team side</li> <li>You have strong communication skills, with the ability to convey complex offensive findings clearly and effectively to both technical and non-technical stakeholders</li> <li>You are comfo