# Senior Security Engineer, Offensive Security

**Company:** [Datadog](https://hotfix.jobs/companies/datadog)
**Location:** New York, NY
**Role:** Security Engineering
**Salary:** $195k – $240k/yr
**Experience:** 5+ years
**Skills:** Python, Go, Red Teaming, Penetration Testing, AWS, GCP, Azure, Kubernetes, CI/CD, Edr, SIEM
**Posted:** 2026-06-10

> 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.

## Job Description

## 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

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