Senior Security Engineer, Offensive Security

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