[Hiring] Senior Engineer, Offensive Security @Humana

Role Description

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 Senior Offensive Security Engineer, AI-Driven Red Team & Tooling, you'll build the AI and agentic tooling that makes our offensive operations faster and broader, then prove it where it counts, on real penetration tests, purple-team exercises, and red-team operations.

You'll also bring that same offensive lens to the enterprise's own AI systems. It's one loop: build the tooling, prove it on live engagements, feed what you learn back into the tooling. And it's a rare chance to do that hands-on inside a program that helps protect the health data of millions of people.

What you'll do

• Build agentic offensive tooling.
• Write production-quality software and AI agents, including:
  • LLM-driven planning loops and multi-agent orchestration.
  • Tool and function-calling capabilities for real offensive tooling.
  • Contribute to the in-house agent platform for pentest and red-team operations.
• Run penetration tests across:
  • Network, web-application, cloud, and infrastructure testing.
  • Recon through exploitation, privilege escalation, and lateral movement.
• Run purple-team exercises to validate security countermeasures with defensive partners.
• Run red-team operations and test the enterprise's own AI, focusing on:
  • Objective-driven adversary emulation.
  • Adversarial assessment of internal LLM-powered products and applications.

Your first 6–12 months

• First 90 days:
  • Ramp on the agent platform and offensive service lines.
  • Deliver your first engagements (a penetration test and a purple-team exercise).
  • Ship one improvement to the agentic tooling used during engagements.
• By 6 months:
  • Ship at least one AI-driven tool adopted into live workflow.
  • Run a red-team operation end to end.
• By 12 months:
  • Stand up repeatable adversarial testing for at least one AI system.
  • Establish an evaluation approach tracking tooling's autonomous success.
  • Become a go-to for both building and operating across the team.

Qualifications

• 4+ years in roles such as Red Team, Penetration Testing, Purple Team/control validation, or Bug Bounty.
• Production Python engineering experience.
• Hands-on designing, building, or operating AI agents or LLM applications.
• Experience testing AI/ML systems: prompt injection, jailbreaking, and adversarial techniques.
• Production experience with at least one major Cloud Service Provider (AWS, GCP, or Azure).

Preferred Qualifications

• Built autonomous or semi-autonomous offensive agents.
• Red-team tradecraft knowledge: C2 frameworks, evasion, and OPSEC.
• Purple-team and adversary-emulation fluency: MITRE ATT&CK, VECTR, or Atomic Red Team.
• Hands-on with AI red-teaming frameworks and fluent in MITRE ATLAS.
• Cloud penetration-testing depth or multi-cloud breadth.
• Published research or contributions to AI-security competitions.
• Certifications in offensive and emerging AI-security fields.

Requirements

• Work with considerable autonomy on moderately complex engagements.
• Embed with each service line and the AI & Tooling Lead.
• Ship software with engineering rigor.
• Deliver findings and tooling with reproduction steps, severity, business impact, and remediation.
• Track risk in the enterprise risk platform.
• Operate within the organization's acceptable-use-of-AI policies.

Benefits

• Medical, dental, and vision benefits.
• 401(k) retirement savings plan.
• Paid time off, including company and personal holidays.
• Paid parental and caregiver leave.
• Short-term and long-term disability.
• Life insurance and many other opportunities.