Senior AI-Driven Offensive Security Engineer (Remote)

Humana Inc; Madison (WI); Remote; USD 118,000 - 162,000; Full time

Benefits offered by this job

Bonus opportunity

Remote position

Job summary

Humana Inc. is seeking a Senior Offensive Security Engineer, AI-Driven Red Team & Tooling to design, build, and operate AI-enabled offensive tooling at scale.

You will execute engagements across networks, applications, and cloud environments, using production-grade AI agents and orchestrated workflows. You will advance tooling through live pentests, purple-team exercises, and end-to-end red-team operations while applying an offensive lens to Humana's enterprise AI systems.

Qualifications

• Offensive operations experience: 4+ years in Red Team, Penetration Testing, Purple Team or Bug Bounty with end-to-end engagements.
• Production Python engineering: build and operate real tooling, not just scripts.
• Agentic AI: hands-on design, build, or operation of AI agents or LLM applications.
• Experience with AI adversarial techniques: prompt injection, jailbreaking, and related methods.
• Cloud fluency: production experience with AWS, GCP, or Azure.

Responsibilities

• Build production-quality AI-driven offensive tooling and agent platforms for red-team operations.
• Run penetration tests across network, web apps, cloud, and infrastructure with your tooling.
• Conduct purple-team exercises to validate defensive controls and close gaps.
• Lead red-team operations and adversarial assessment of AI systems and LLM-powered products.

Skills

Offensive operations

Production Python engineering

Agentic AI

AI adversarial testing

Cloud fluency

Tools

Cobalt Strike

Sliver

Mythic

EDR/XDR

MITRE ATT&CK

VECTR

Atomic Red Team

PyRIT

Garak

Job description

Humana Inc. is seeking a Senior Offensive Security Engineer, AI-Driven Red Team & Tooling to design, build, and operate AI-enabled offensive tooling at scale.

You will execute engagements across networks, applications, and cloud environments, using production-grade AI agents and orchestrated workflows. You will advance tooling through live pentests, purple-team exercises, and end-to-end red-team operations while applying an offensive lens to Humana's enterprise AI systems.