Senior Security Engineer, Offensive Security
Senior Security Engineer executing sophisticated red team operations, building custom offensive tooling, and applying AI/automation to scale adversary simulations across cloud and Kubernetes environments.
About the job
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
- 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
- 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
- Deep expertise in at least two of the following areas: macOS security, Linux security, cloud platforms (AWS, GCP, Azure), Kubernetes, or CI/CD pipelines
- Experience developing evasion techniques against modern defensive controls and understand how detections work from the blue team side
- Strong communication skills, with the ability to convey complex offensive findings clearly and effectively to both technical and non-technical stakeholders
- Comfortable operating with ambiguity, scoping your own work, identifying what matters most, and driving projects from prototype to deployed and validated
Skills
Python, Go, Red Teaming, Penetration Testing, AWS, GCP, Azure, Kubernetes, CI/CD, Edr, SIEM
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