Offensive Security Engineer Jobs

About The Position

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
• vision
• 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
• bonus incentive plan