Offensive Security Analyst (Structured / Non-Exploit)
- Montreal, Quebec, Canada
- Remote
- Posted Oct 8, 2026
- 1 position
US$40–US$60 / hour
Opens LinkedIn
- Employment type
- Contract
- Experience level
- Mid-level · 2+ years
- Posting language
- English
- Working hours
- 40 hours per week
- Location requirements
- Country, Montreal, Quebec, Canada
- Seniority
- Mid-Senior level
Job summary
Analyze attack paths, adversary strategies, system weaknesses, and defensive gaps, then evaluate red-team narratives and threat-modeling scenarios. Create and validate structured adversarial reasoning data for AI training and benchmarking, clearly communicating attack chains, business impact, and security tradeoffs.
Job details
Offensive Security Analyst (Structured / Non-Exploit) — AI Training About The Role What if your ability to think like an adversary could directly shape how AI understands and reasons about cybersecurity threats? We're looking for Offensive Security Analysts to bring real-world attack knowledge to one of the most impactful applications in tech today — training and evaluating cutting-edge AI systems. This role is about structured adversarial reasoning, not exploit development. You'll work with realistic attack scenarios, model how threats move through systems, expose where defenses fail, and articulate how risk propagates across modern environments. No CVE writing. No shellcode. Just deep, strategic security thinking applied to frontier AI. This is a fully remote, flexible contract role built for experienced security professionals who want to do meaningful work on their own schedule. Organization: Alignerr Type: Hourly Contract Location: Remote Commitment: 10–40 hours/week What You'll Do Analyze attack paths, kill chains, and adversary strategies across realistic, production-style environments Identify weaknesses, misconfigurations, and defensive gaps in complex system architectures Review and evaluate red-team narratives, intrusion scenarios, and threat modeling exercises Generate, label, and validate adversarial reasoning data used to train and benchmark AI systems Clearly articulate attack chains, business impact, and security tradeoffs in structured formats Work independently and asynchronously — fully on your own schedule Who You Are 2+ years of hands-on experience in pentesting, red teaming, or blue-team security with deep attack knowledge You understand how real attacks unfold — not just in theory, but in live production environments You can break down complex attack chains and communicate them clearly and precisely Comfortable working with ambiguity and applying structured thinking to open-ended security scenarios Detail-oriented and consistent — you bring rigor to everything you analyze Nice to Have Experience with threat modeling frameworks (MITRE ATT&CK, STRIDE, PASTA, etc.) Background in incident response, threat intelligence, or adversary simulation Familiarity with cloud environments, Active Directory attack paths, or lateral movement techniques Prior experience writing security assessments, red team reports, or technical narratives Interest in AI safety, AI security, or responsible AI development Why Join Us Work directly on frontier AI systems alongside leading research labs Fully remote and flexible — work when and where it suits you Freelance autonomy with the structure of meaningful, task-based work Apply your offensive security expertise to a field that's actively shaping the future of technology Potential for ongoing work and contract extension as new projects launch
What you’ll do
Analyze attack paths, adversary strategies, system weaknesses, and defensive gaps, then evaluate red-team narratives and threat-modeling scenarios. Create and validate structured adversarial reasoning data for AI training and benchmarking, clearly communicating attack chains, business impact, and security tradeoffs.
Requirements
Requires at least two years of hands-on experience in penetration testing, red teaming, or blue-team security, with practical knowledge of how attacks unfold in production environments. Candidates should be able to analyze complex attack chains, communicate precisely, work independently with ambiguity, and apply rigorous structured thinking.
Benefits
- Fully Remote Work
- Flexible Schedule
- Freelance Autonomy
- Potential for Ongoing Work and Contract Extension
Listed skills
- Active Directory · Preferred
Other relevant skills
Identified from the job description. Confirm important requirements above.
- Offensive Security Analysis
- Penetration Testing
- Red Teaming
- Blue-Team Security
- Attack Path Analysis
- Threat Modeling
- Adversarial Reasoning
- Security Assessment
- Incident Response
- Threat Intelligence
- Adversary Simulation
- Cloud Security
- Active Directory
- Lateral Movement Analysis
- Security Reporting
- AI Security
Job areas
- Security & Safety
- Technology
- Software
- Data & Analytics
- Science & Research
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