Humana

Senior Engineer, Offensive Security

Remote Offensive Security role with clear candidate location fit.

PostedJul 5, 2026

Eligible countries1 accepted country

Seniority signalSenior

Work settingRemote

Accepted candidate locations

USA

Role overview

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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 that you 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.

Build and operate (both, for real). Most offensive roles let you build or operate. This one is explicitly both: you ship the software and you run the engagements, so your tooling is shaped by someone who actually uses it.
A program that's already serious about AI. Fridays are dedicated to R&D. You'll have Hack The Box Pro Labs, all HTB role-based paths and certifications, discretionary certification funding, and conference/training budgets. You'll work alongside the Lead of our new AI & Offensive Tooling capability—contributing to the platform they own while running your own engagements.
Mission that matters. Offensive Security identifies weaknesses so the business can fix them before adversaries exploit them, protecting the data and care of millions of people. AI is entering both our adversaries' tradecraft and our own operations faster than traditional tooling keeps up; you help keep us ahead.

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. (We care about what you've shipped and operated, not years on a particular framework—these frameworks are only a few years old.)
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).

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).

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