Senior Security Engineer, Offensive Security

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. 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 You have 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 (Python, Go, or similar), can build your own tools, and automate your workflows rather than relying exclusively on off-the-shelf frameworks You have 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 You have experience developing evasion techniques against modern defensive controls and understand how detections work from the blue team side You have strong communication skills, with the ability to convey complex offensive findings clearly and effectively to both technical and non-technical stakeholders You are comfortable operating with ambiguity, scoping your own work, identifying what matters most, and driving projects from prototype to deployed and validated Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That’s okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply. Benefits and Growth 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 #LI-Hybrid Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate’s skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan. The reasonably estimated yearly salary for this role at Datadog is: $195,000 - $240,000 USD About Datadog Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center. Equal Opportunity at Datadog Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference. #J-18808-Ljbffr