Senior AI-Driven Offensive Security Engineer

Humana Inc; Dover (DE); On-site; EUR 105,000 - 144,000; Full time

Benefits offered by this job

Bonus incentive plan

Medical, dental and vision benefits

Paid time off

Job summary

Humana Inc in a remote setup seeks a Senior Offensive Security Engineer, AI-Driven Red Team & Tooling. You will build production-grade AI agents and toolchains for offensive testing, then prove them in live engagements such as penetration tests and purple-team exercises, feeding lessons back into the tooling.

You’ll run red-team operations and evaluate the enterprise's AI systems, work across cloud environments, and balance building with operating deployments.

Qualifications

• 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).

Responsibilities

• Build agentic offensive tooling: write production-quality software and AI agents; develop tool and function-calling capabilities; contribute to in-house agent platform for pentest and red-team operations.
• Run penetration tests: network, web-app, cloud, and infrastructure testing, accelerated by tooling.
• Run purple-team exercises: validate security countermeasures with defensive partners and close gaps revealed by attacks.
• Run red-team operations and test the enterprise's own AI: adversary emulation and evaluation of internal LLM-powered products and RAG pipelines.

Skills

Offensive operations experience

Production Python engineering

Agentic AI tools

AI adversarial testing

Cloud fluency

Tools

Cobalt Strike

Sliver

Mythic

Job description

Humana Inc in a remote setup seeks a Senior Offensive Security Engineer, AI-Driven Red Team & Tooling. You will build production-grade AI agents and toolchains for offensive testing, then prove them in live engagements such as penetration tests and purple-team exercises, feeding lessons back into the tooling.

You’ll run red-team operations and evaluate the enterprise's AI systems, work across cloud environments, and balance building with operating deployments.