Senior Security Engineer, Offensive Security

Datadog seeks a Senior Security Engineer, Offensive Security in New York, NY (hybrid) to plan, execute, and automate red team engagements and build AI-first offensive tooling for cloud-native environments.

Responsibilities

• Lead end-to-end red team operations, 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 discipline
• Develop tailored payloads and evasion techniques aligned with Datadog's environment and modern defensive controls (EDR, SIEM, network monitoring)
• Boost the efficiency of offensive activities through automation and AI, expediting reconnaissance, vulnerability analysis, and reporting workflows
• Collaborate with the Detection & Response team on purple team exercises to validate detections, improve alert fidelity, and influence threat models
• Translate offensive findings into concrete improvements by partnering with defensive security and engineering teams to close gaps

Requirements

• 5+ years of hands-on offensive security experience (red teaming, penetration testing, or adversary simulation) with a track record in mature, well-defended environments
• Production-quality coding skills (Python, Go, or similar), ability to build tools, and automation of workflows rather than relying solely 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 understanding detections from the blue team perspective
• Strong communication skills, able to convey complex offensive findings clearly to technical and non-technical stakeholders
• Comfort operating with ambiguity, scoping work, prioritizing what matters, and driving projects from prototype to deployed and validated

Technologies

• AWS
• GCP
• Azure
• Kubernetes
• CI/CD pipelines
• Python
• Go
• EDR
• SIEM

Benefits

• New hire stock equity (RSUs) and employee stock purchase plan (ESPP)
• Continuous professional development, product training, and career pathing
• Intradepartmental mentor and buddy program for in-house networking
• Inclusive culture with access to Community Guilds (Datadog employee resource groups)
• Free global mental health benefits for employees and dependents age 6+
• Competitive global benefits