SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 195,000 - 240,000 / annual
Datadog is seeking a Senior Security Engineer to lead offensive security operations and red team engagements. In this role, you will plan and execute sophisticated red team operations simulating real-world threat actors across cloud infrastructure (AWS, GCP), Kubernetes, CI/CD pipelines, and corporate environments. You'll build and maintain custom offensive tooling, automation frameworks, and engagement infrastructure, treating offensive operations as a software engineering problem.
Key responsibilities include developing custom payloads and evasion capabilities tailored to Datadog's environment and modern defensive controls (EDR, SIEM, network monitoring). You'll improve the efficiency of offensive operations through thoughtful use of automation and AI, accelerating reconnaissance, vulnerability analysis, and reporting workflows. You'll partner with the Detection & Response team on purple team exercises to validate detection logic, improve alert fidelity, and influence threat models. Finally, you'll translate offensive findings into concrete improvements by working directly with defensive security and engineering teams to close gaps.
You bring 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 in Python, Go, or similar languages, can build your own tools, and automate workflows rather than relying exclusively on off-the-shelf frameworks. You have deep expertise in at least two areas: macOS security, Linux security, cloud platforms (AWS, GCP, Azure), Kubernetes, or CI/CD pipelines. You have experience developing evasion techniques against modern defensive controls and understand how detections work from the blue team side. Strong communication skills are essential—you can convey complex offensive findings clearly to both technical and non-technical stakeholders. You're comfortable operating with ambiguity, scoping your own work, identifying what matters most, and driving projects from prototype to deployed and validated.
