Senior Engineer, Offensive Security

Posted 5hrs ago

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Job Description

Senior offensive security engineer building AI-driven red-team tooling for Humana's healthcare and health-data systems. Running penetration tests, purple-team exercises, and adversarial assessments of enterprise AI.

Responsibilities:

Build production-quality AI agents and offensive security tooling, including LLM-driven planning loops, multi-agent orchestration, and tool/function-calling
Contribute to the in-house agent platform powering penetration testing and red-team operations
Operate the tooling as a production, event-driven cloud platform with serverless functions, change-stream pipelines, alarms, and integrated LLM inference
Run network, web-application, cloud, and infrastructure penetration tests from reconnaissance through exploitation, privilege escalation, and lateral movement
Run purple-team exercises validating EDR/XDR, NDR, DLP, and firewall countermeasures
Partner with detection engineering to close gaps identified through offensive testing
Conduct objective-driven red-team operations and adversarial assessments of internal LLM products, agents, RAG pipelines, and ML applications
Test prompt injection, jailbreaks, model extraction and inversion, membership inference, poisoning, evasion, and agent tool/sandbox abuse
Deliver penetration tests and purple-team exercises during the first 90 days and ship improvements to agentic tooling
Ship AI-driven tools adopted into live workflows, run an end-to-end red-team operation, and establish repeatable adversarial testing and evaluation approaches
Embed with service lines and the AI & Tooling Lead while influencing technical direction
Deliver findings and tooling with reproduction steps, severity, business impact, and remediation
Track risk in the enterprise risk platform and follow acceptable-use-of-AI policies and rules of engagement

Requirements:

4+ years of offensive operations experience in red team, penetration testing, purple team/control validation, or bug bounty roles
Track record delivering engagements end to end, including scoping, execution, and clear written findings
Production Python engineering experience building and operating real tooling
Hands-on experience designing, building, or operating AI agents or LLM applications
Experience with agentic workflows, tool/function-calling, and orchestration
Hands-on testing of AI/ML systems, including prompt injection, jailbreaking, and adversarial techniques
Production experience with at least one major cloud service provider: AWS, GCP, or Azure
Ability to work with considerable autonomy on moderately complex engagements
Ability to produce reproducible software with evaluation, safety guardrails, and human-in-the-loop controls where required
Ability to deliver findings with reproduction steps, severity, business impact, and remediation
Ability to track risk in an enterprise risk platform and follow AI acceptable-use policies and offensive security rules of engagement
Selected candidate must reside within approximately 60 minutes driving distance of an eligible location
Home internet must provide at least 25 Mbps download and 10 Mbps upload
Must work from a dedicated space without ongoing interruptions to protect PHI/HIPAA information
Preferred: autonomous offensive agents, C2 frameworks, evasion/OPSEC, EDR/XDR, MITRE ATT&CK, VECTR, Atomic Red Team, PyRIT, Garak, MITRE ATLAS, OWASP Top 10 for LLM Applications, NIST AI Risk Management Framework, MCP, RAG pipelines, cloud penetration testing, threat intelligence, advanced offensive specialties, research/open-source/talk experience, and relevant certifications

Benefits:

Bonus incentive plan
Fridays dedicated to R&D
Hack The Box Pro Labs
All HTB role-based paths and certifications
Discretionary certification funding
Conference/training budgets
Medical benefits
Dental benefits
Vision benefits
401(k) retirement savings plan
Paid time off
Company holidays
Personal holidays
Paid parental leave
Paid caregiver leave
Short-term disability
Long-term disability
Life insurance
Other whole-person wellness and healthcare benefits

Senior Engineer, Offensive Security

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