Senior Security Engineer, Offensive Security

Datadog•New York, NY

9h•Hybrid

About The Position

Here at Datadog, we think about offensive security a little bit differently. We embrace automation and AI to run adversary simulations continuously across a massive cloud-native environment, and we expect our offensive engineers to build the tooling that makes that possible. We're looking for a Senior Security Engineer who can execute sophisticated red team operations, write the code that scales them, and take an AI-first approach to offensive security engineering. At Datadog, we place value in our office culture - the relationships and collaboration it builds, and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them.

Requirements

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 a 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

Responsibilities

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

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
An inclusive company culture, ability to join our Community Guilds (Datadog employee resource groups)
Free, global mental health benefits for employees and dependents age 6+
Competitive global benefits
healthcare
dental
parental planning
mental health benefits
a 401(k) plan and match
paid time off
fitness reimbursements
a discounted employee stock purchase plan