Senior Engineer, Offensive Security

** Become a part of our caring community*
* 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.

** What you'll do*
* ** One integrated mission, four ways it shows up:*
* ** 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.

** Your first 6-12 months*
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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.

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** 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.

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** 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.

** Why this role, and why here*
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** 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.

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** 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.

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** 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.

** Use your skills to make an impact*
* Additional

Job Description

** What we're looking for*
* We're hiring for a genuinely hybrid skill set, real offensive operations  
** and
* * real AI engineering.  
** You do not need to check every box below.
** We expect depth in one half and real credibility plus a desire to grow in the other, not day-one mastery of both. If you're a strong offensive operator who has built real AI tooling, or a strong AI/agent builder with serious…