Senior Engineer, Offensive Security

Location Selected candidate must reside within approximately 60 minutes driving distance from one of the following locations: Louisville KY, NYC Metro, Dallas Metro, Charlotte NC Metro, South Florida (Tampa/Miami/Ft Lauderdale), Washington DC metro, Chicago, Boston, Atlanta, Nashville. About the Role We're building a new AI & Offensive Tooling capability inside our Offensive Security organization, and we’re looking for a senior engineer who can both build it and use it. As a Senior Offensive Security Engineer, AI-Driven Red Team & Tooling, you will develop AI and agentic tooling that makes our offensive operations faster and broader, then prove it in real penetration tests, purple‑team exercises, and red‑team operations. You will also bring that same offensive lens to the enterprise’s own AI systems. What You’ll Do Build agentic offensive tooling. Write production‑quality software and AI agents, LLM‑driven planning loops, multi‑agent orchestration, and tool/function‑calling that drives real offensive tooling. Contribute to the in‑house agent platform that powers our pentest and red‑team operations, operating it as a production, event‑driven cloud platform at real scale. Run penetration tests. Conduct network, web‑application, cloud, and infrastructure testing, recon through exploitation, privilege escalation, and lateral movement, accelerated by the tooling you build. Run purple‑team exercises. Validate security countermeasures (EDR/XDR, NDR, DLP, firewalls) with our defensive partners, then pair with detection engineering to close gaps revealed by your attacks. Run red‑team operations and test the enterprise’s own AI. Execute objective‑driven adversary emulation and adversarial assessment of internal LLM‑powered products, agents, RAG pipelines, and ML applications to confirm guardrails and classifiers hold up. First 6–12 Months First 90 days: ramp on the agent platform and the offensive service lines; deliver your first engagements (a penetration test and a purple‑team exercise) and ship one improvement to the agentic tooling used during them. By 6 months: ship at least one AI‑driven tool that a service line adopts into its live workflow, with metrics showing coverage or turnaround gains; run a red‑team operation end to end. By 12 months: stand up repeatable adversarial testing for at least one of the enterprise’s own AI systems; establish an evaluation approach that tracks your tooling’s autonomous success against representative targets; become a go‑to for both building and operating across the team. Why This Role, and Why Here Build and operate (both, for real). This role explicitly lets you ship software and run engagements. A program serious about AI. Dedicated R&D Fridays, Hack The Box Pro Labs, role‑based paths, certification funding, and conference budgets. Mission that matters. Offensive Security protects the data and care of millions of people; AI is accelerating both adversary tradecraft and our own operations. What We’re Looking For We're hiring for a genuinely hybrid skill set, real offensive operations and real AI engineering. You do not need to check every box. Depth in one half and real credibility plus a desire to grow in the other are required. Required Qualifications Offensive operations experience: 4+ years in Red Team, Penetration Testing, Purple Team, or Bug Bounty with a track record of end‑to‑end engagements. Production Python engineering: build and operate real tooling, not one‑off scripts. Hands‑on with agentic AI: design, build, or operate AI agents or LLM applications, including 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). Preferred Qualifications Built autonomous or semi‑autonomous offensive agents, LLM‑driven penetration‑testing agents, or reinforcement‑learning exploit planners. Red‑team tradecraft: C2 frameworks, evasion, OPSEC, and testing endpoints protected by modern EDR/XDR. Purple‑team fluency: MITRE ATT&CK, VECTR, Atomic Red Team. Experience with AI red‑team frameworks such as PyRIT or Garak, and knowledge of MITRE ATLAS, the OWASP Top 10 for LLM Applications, and the NIST AI Risk Management Framework. Model Context Protocol (MCP) and RAG pipeline expertise for tool/prompt‑injection abuse. Cloud penetration‑testing depth or multi‑cloud breadth; threat‑intelligence‑driven operations; advanced offensive specialty depth. Published research, open‑source contributions, or talks at DEF CON, BSides, or Black Hat; strong showings in AI‑security competitions. Certifications are a plus, not a gate (e.g., OSCP, OSEP, OSCE3, CRTO, CRTL, CPTS, CWES, CWEE, CAPE, OffSec AI Red Teamer). How You’ll Work You will work with considerable autonomy on moderately complex engagements and influence the team’s technical direction. You’ll embed with each service line and the AI & Tooling Lead, ship software with engineering rigor, deliver findings with severity and remediation, track risk in the enterprise risk platform, and operate within the organization’s acceptable‑use‑of‑AI policies. Work at Home Requirements Minimum home internet download speed 25 Mbps and upload speed 10 Mbps. You must work from a dedicated space free of interruptions to protect PHI/HIPAA information. Occasional travel to Humana offices for training or meetings may be required. Scheduled Weekly Hours 40 Pay Range $117,600 – $161,700 per year. This job is eligible for a bonus incentive plan based on company and/or individual performance. Description Of Benefits Humana, Inc. offers competitive benefits that support whole‑person well‑being: medical, dental and vision benefits, 401(k) retirement savings plan, paid time off, holidays, paid parental and caregiver leave, short‑term and long‑term disability, life insurance, and more. About Us Humana Inc. (NYSE: HUM) is a leading U.S. healthcare company. Through Humana insurance services and CenterWell healthcare services, we help millions of people achieve their best health. Learn more at Humana.com and CenterWell.com. Equal Opportunity Employer Humana does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status. Humana takes affirmative action and bases all employment decisions on valid job requirements. #J-18808-Ljbffr Humana