Lead, Offensive Security
About the role
We're standing up a new AI & Offensive Tooling capability inside our Offensive Security organization, and we're looking for its founding engineer. As Lead, Offensive Security (AI & Tooling), you will own the in-house AI agent platform that powers our penetration testing and red team operations, and build the AI-driven tooling that makes every offensive service line faster, broader, and more autonomous.
Responsibilities
- Ramp on the agent platform and the three service lines (Red Team, BAS, Penetration Testing)
- Take operational ownership
- Ship one meaningful improvement to the agent's autonomous capability or reliability, measured against real engagements
- Deliver at least one AI-driven tool that a service line adopts into its live workflow, with metrics showing coverage or turnaround gains
- Establish the evaluation harness that tracks the agent's autonomous success rate against representative targets
- Publish the multi-quarter offensive-AI roadmap and KPIs
- Stand up repeatable adversarial testing for the enterprise's own AI systems
- Mentor 1–3 engineers as the capability grows toward its own function
Requirements
- Offensive security depth: 6+ years in roles such as Red Team or Penetration Testing, including team- or program-level leadership, and the instinct to think like an attacker against systems that don't behave deterministically
- Production Python engineering: a strong track record of building and operating production-quality software and tooling, not only scripts
- Hands-on designing, building, or operating 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
- Cloud fluency: production experience with at least one major Cloud Service Provider (AWS, GCP, or Azure)
Qualifications
- Built autonomous or semi-autonomous offensive agents, LLM-driven penetration-testing agents, or reinforcement-learning exploit and attack-path planners
- 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
- Demonstrated ability to test endpoints protected by modern EDR/XDR; experience across multiple cloud providers; threat-intelligence-driven operations
- Depth in an advanced offensive specialty: malware development, advanced Red Team operations and threat simulation, or adversarial ML research; experience building and breaking LLMs, ML models, and AI infrastructure
- Published research, open-source contributions, or talks at DEF CON, BSides, x33fcon, or Black Hat; expert-level certifications (e.g. OSEE, OSED, OSCE3, CRTL, CWEE, CAPE)
Skills
To make an impact, you should have a genuine hybrid skill set, deep offensive security and real AI engineering. You do not need to check every box below. If you're a strong offensive engineer who has built real AI agents, or a strong AI/agent builder with serious hands-on offensive experience, we want to hear from you.
Benefits
- Medical, dental and vision benefits
- 401(k) retirement savings plan
- Time off (including paid time off, company and personal holidays, paid parental and caregiver leave)
- Short-term and long-term disability
- Lifetime life insurance
- Many other opportunities
Pay
The compensation range below reflects a good faith estimate of starting base pay for full time (40 hours per week) employment at the time of posting. The pay range may be higher or lower based on geographic location and individual pay will vary based on demonstrated job related skills, knowledge, experience, education, certifications, etc.
$142,300 - $195,700 per year
Schedule
This is a remote position, with occasional travel to Humana's offices for training or meetings may be required. Scheduled Weekly Hours 40