Offensive Security Engineer: Red/Purple Team & AI Tools

Jobtailor; California (MO); On-site; USD 180,000 - 280,000; Full time

Job summary

Jobtailor is seeking a senior red team specialist to conduct offensive security engagements across cloud, endpoints, and hardware deployments. You will simulate advanced threat actors, test high-value deployments, and contribute to AI-assisted testing tooling.

You will translate findings into risk insights for security roadmaps, document clearly for technical and executive audiences, and collaborate with blue and engineering teams on AI safety scenarios.

Qualifications

• 5+ years of hands-on red teaming and offensive security operations.
• Deep expertise in at least two domains (cloud security, macOS/Linux security, Kubernetes).
• Proven track record discovering novel attack vectors and chaining vulnerabilities.
• Experience conducting adversarial simulations against well-defended environments.
• Strong engineering skills in Python, Go, or similar; ability to write clear findings.

Responsibilities

• Conduct red and purple team engagements across cloud infrastructure, endpoints, and bare metal deployments.
• Penetration test high-value deployments.
• Contribute to AI-assisted security testing tooling and workflows.
• Work cross-functionally with security and engineering teams, especially on AI-specific attack scenarios.
• Document and present findings to technical and executive audiences.
• Translate attack narratives into actionable risk insights informing security roadmaps.

Skills

Red Teaming

Offensive Security Operations

Cloud Security (GCP/AWS/Azure)

Python Programming

Penetration Testing

Go Programming

Kubernetes

CI/CD Pipelines

Adversarial Simulations

Vulnerability Discovery

Education

Bachelor's degree or equivalent

Tools

SIEM Platforms

EDR Platforms

AI Safety Tools

Detection Engineering

Job description

Jobtailor is seeking a senior red team specialist to conduct offensive security engagements across cloud, endpoints, and hardware deployments. You will simulate advanced threat actors, test high-value deployments, and contribute to AI-assisted testing tooling.

You will translate findings into risk insights for security roadmaps, document clearly for technical and executive audiences, and collaborate with blue and engineering teams on AI safety scenarios.