Senior Security Engineer, Offensive Security

Datadog Datadog · Enterprise · New York, NY · Security

Senior Security Engineer focused on offensive security, leveraging AI and automation to execute sophisticated red team operations and build scalable tooling. The role involves planning and executing red team engagements, developing custom offensive tooling and evasion capabilities, and improving operational efficiency through AI.

What you'd actually do

  1. 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
  2. Build and maintain custom offensive tooling, automation frameworks, and engagement infrastructure, treating offensive operations as a software engineering problem
  3. Develop custom payloads and evasion capabilities tailored to Datadog's environment and modern defensive controls (EDR, SIEM, network monitoring)
  4. Improve the efficiency of offensive operations through thoughtful use of automation and AI, accelerating reconnaissance, vulnerability analysis, and reporting workflows
  5. Partner with the Detection & Response team on purple team exercises to validate detection logic, improve alert fidelity, and influence threat models

Skills

Required

  • 5+ years of hands-on experience in offensive security (red teaming, penetration testing, or adversary simulation)
  • Track record of operating against mature, well-defended environments
  • Production-quality code (Python, Go, or similar)
  • Build your own tools
  • Automate your workflows
  • 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
  • Understand how detections work from the blue team side
  • Strong communication skills
  • Comfortable operating with ambiguity
  • Scoping your own work
  • Identifying what matters most
  • Driving projects from prototype to deployed and validated

Nice to have

  • AI tools

What the JD emphasized

  • AI-first approach
  • production-quality code
  • automate your workflows

Other signals

  • AI-first approach to offensive security engineering
  • Improve efficiency of offensive operations through thoughtful use of automation and AI
  • Treating offensive operations as a software engineering problem