Senior Engineer, Offensive Security

Humana

1d • $117,600 - $161,700 • Remote

About The Position

The Senior Offensive Security Engineer designs, organizes, and oversees program and team-level activities intended to simulate threat actors and pressure test Humana’s defenses, ability to respond to adversaries, and security controls. The Senior Offensive Security Engineer work assignments involve moderately complex to complex issues where the analysis of situations or data requires an in-depth evaluation of variable factors.

Requirements

• 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).

Nice To Haves

• Built autonomous or semi-autonomous offensive agents, LLM-driven penetration-testing agents, or reinforcement-learning exploit and attack-path planners.
• Red-team tradecraft: C2 frameworks (e.g. Cobalt Strike, Sliver, Mythic), evasion and OPSEC, and testing endpoints protected by modern EDR/XDR.
• Purple-team and adversary-emulation fluency: MITRE ATT&CK, and platforms such as VECTR or Atomic Red Team.
• Hands-on with AI red-teaming frameworks such as PyRIT or Garak, and 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.
• Cloud penetration-testing depth or multi-cloud breadth; threat-intelligence-driven operations; depth in an advanced offensive specialty (malware development, advanced red-team operations, or adversarial ML research).
• Published research, open-source contributions, or talks at DEF CON (incl. the AI Village / Generative Red Team), BSides, x33fcon, or Black Hat, or strong showings in AI-security competitions like HackAPrompt.
• Certifications are a plus, not a gate, offensive (e.g. OSCP, OSEP, OSED, OSCE3, CRTO, CRTL, CPTS, CWES, CWEE, CAPE) and emerging AI-security (e.g. the OffSec AI Red Teamer (OSAI / AI-300), the SANS/GIAC AI security line, the HTB AI Red Teamer path).

Responsibilities

• 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, and contribute to the in-house agent platform that powers our pentest and red-team operations. You'll operate this as a production, event-driven cloud platform at real scale (dozens of serverless functions, change-stream data pipelines, hundreds of operational alarms, integrated LLM inference), real software engineering, not proof-of-concept scripting.
• Run penetration tests. Network, web-application, cloud, and infrastructure testing, recon through exploitation, privilege escalation, and lateral movement, accelerated by the tooling you build, with your own judgment owning scope and exploitability.
• Run purple-team exercises. Validate security countermeasures (EDR/XDR, NDR, DLP, firewalls) with our defensive partners, then pair with detection engineering to close the gaps your attacks reveal.
• Run red-team operations and test the enterprise's own AI. Objective-driven adversary emulation; and adversarial assessment of internal LLM-powered products, agents, RAG pipelines, and ML applications, prompt injection, jailbreaks, model extraction and inversion, membership inference, data and supply-chain poisoning, evasion, and agent tool/sandbox abuse, validating that guardrails and classifiers actually hold.
• 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 and offensive security rules of engagement.

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
• life insurance
• Hack The Box Pro Labs
• all HTB role-based paths and certifications
• discretionary certification funding
• conference/training budgets

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed