Senior Offensive Security Engineer, AI-Driven Tooling

Humana Inc; Hartford (CT); Remote; USD 118,000 - 162,000; Full time

Job summary

Humana Inc. is seeking a Senior Offensive Security Engineer to build AI-driven tooling and to execute live penetration tests, purple-team exercises, and red-team operations. You’ll apply an offensive lens to Humana's AI systems and enterprise security, delivering production-grade AI agents and orchestrated tooling at scale.

The role emphasizes hands-on engineering and real-world engagements, with remote-enabled flexibility and a focus on safeguarding patient data across healthcare services.

Qualifications

• 4+ years in roles such as Red Team, Penetration Testing, Purple Team / control validation, or Bug Bounty, with a track record of delivering engagements end to end: scoping, execution, and clear written findings.
• You build and operate real tooling, not only one-off scripts.
• Hands-over design/operation of AI agents or LLM applications: agentic workflows, tool/function-calling, and orchestration.
• Hands-on testing of AI/ML systems: prompt injection, jailbreaking, and adversarial techniques.
• Production experience with AWS, GCP, or Azure.

Responsibilities

• Build agentic offensive tooling.
• Run penetration tests.
• Run purple-team exercises.
• Run red-team operations and test the enterprise's own AI.

Skills

Offensive operations experience

Production Python engineering

Agentic AI experience

AI security testing

Cloud fluency

Job description

Humana Inc. is seeking a Senior Offensive Security Engineer to build AI-driven tooling and to execute live penetration tests, purple-team exercises, and red-team operations. You’ll apply an offensive lens to Humana's AI systems and enterprise security, delivering production-grade AI agents and orchestrated tooling at scale.

The role emphasizes hands-on engineering and real-world engagements, with remote-enabled flexibility and a focus on safeguarding patient data across healthcare services.