Senior Engineer, Offensive Security

Humana Inc. is a leading U.S. healthcare company, and they are seeking a Senior Engineer in Offensive Security. The role involves designing and overseeing activities to simulate threat actors, running penetration tests, and validating security measures, while also contributing to the development of offensive tooling.

Responsibilities:

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

Requirements:

• Offensive operations experience: 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
• Production Python engineering: you build and operate real tooling, not only one-off scripts
• You've built with agentic AI: hands-on designing, building, or operating AI agents or LLM applications: agentic workflows, tool/function-calling, and orchestration
• You've attacked AI: hands-on testing of AI/ML systems: prompt injection, jailbreaking, and adversarial techniques
• Cloud fluency: production experience with at least one major Cloud Service Provider (AWS, GCP, or Azure)
• Built autonomous or semi-autonomous offensive agents, LLM-driven penetration-testing agents, or reinforcement-learning exploit and attack-path planners
• Red-team tradecraft: C2 frameworks (e.g. Cobalt Strike, Sliver, Mythic), evasion and OPSEC, and testing endpoints protected by modern EDR/XDR
• Purple-team and adversary-emulation fluency: MITRE ATT&CK, and platforms such as VECTR or Atomic Red Team
• Hands-on with AI red-teaming frameworks such as PyRIT or Garak, and fluent in MITRE ATLAS, the OWASP Top 10 for LLM Applications, and the NIST AI Risk Management Framework
• Model Context Protocol (MCP), building clients/servers, or testing them and RAG pipelines for tool/prompt-injection abuse
• Cloud penetration-testing depth or multi-cloud breadth; threat-intelligence-driven operations; depth in an advanced offensive specialty (malware development, advanced red-team operations, or adversarial ML research)
• Published research, open-source contributions, or talks at DEF CON (incl. the AI Village / Generative Red Team), BSides, x33fcon, or Black Hat, or strong showings in AI-security competitions like HackAPrompt
• Certifications are a plus, not a gate, offensive (e.g. OSCP, OSEP, OSED, OSCE3, CRTO, CRTL, CPTS, CWES, CWEE, CAPE) and emerging AI-security (e.g. the OffSec AI Red Teamer (OSAI / AI-300), the SANS/GIAC AI security line, the HTB AI Red Teamer path)
• Work from a dedicated space lacking ongoing interruptions to protect member PHI / HIPAA information
• Occasional travel to Humana's offices for training or meetings may be required