From $195K/yr
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. 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. What You'll Do: 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 Build and maintain custom offensive tooling, automation frameworks, and engagement infrastructure, treating offensive operations as a software engineering problem Develop custom payloads and evasion capabilities tailored to Datadog's environment and modern defensive controls (EDR, SIEM, network monitoring) Improve the efficiency of offensive operations through thoughtful use of automation and AI, accelerating reconnaissance, vulnerability analysis, and reporting workflows Partner with the Detection & Response team on purple team exercises to validate detection logic, improve alert fidelity, and influence threat models Translate offensive findings into concrete improvements by working directly with defensive security and engineering teams to close gaps Who You Are: 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 You write production-quality code (Python, Go, or similar), can build your own tools, and automate your w