About The Role
What if your knowledge of how attacks unfold — the kill chains, the lateral movement, the overlooked misconfigurations — could directly shape how AI understands and reasons about cybersecurity threats? We're looking for Offensive Security Analysts to bring real-world adversarial thinking to cutting-edge AI development. This isn't about writing exploits. It's about structured reasoning: mapping how attackers move through systems, where defenses break down, and how risk cascades across modern environments. Your expertise becomes the foundation that makes AI smarter about security. This is a fully remote, flexible contract role built for experienced security professionals who want meaningful, high-impact work on their own schedule.
• Organization: Alignerr
• Type: Hourly Contract
•

Location:
Remote
• Commitment: 10–40 hours/week

What You'll Do
• Analyze realistic attack paths, kill chains, and adversary strategies across modern production environments
• Classify weaknesses, misconfigurations, and defensive gaps in structured, reviewable formats
• Evaluate red team-style scenarios and intrusion narratives for accuracy, depth, and realism
• Generate, label, and validate adversarial reasoning data used to train and evaluate AI security systems
• Clearly articulate attack chains, impact assessments, and risk tradeoffs in writing




• Work independently and asynchronously — fully on your own schedule Who You Are
• 2+ years of hands-on experience in pentesting, red teaming, or a blue-team role with deep offensive knowledge
• You understand how real attacks unfold — not just in theory, but in messy, real-world production systems
• You can think like an attacker and communicate it clearly — translating complex threat scenarios into structured, actionable analysis
• Detail-oriented and methodical, with a consistent approach to evaluating adversarial risk
• Comfortable working independently without close supervision Nice to Have
• Experience with threat modeling, adversary emulation, or purple team exercises
• Familiarity with frameworks like MITRE ATT&CK;, Cyber Kill Chain, or STRIDE
• Background in cloud security, network security, or endpoint detection
• Prior exposure to AI systems, data labeling, or structured evaluation workflows
• Strong technical writing or documentation skills 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
• Make a tangible impact on how AI understands and reasons about real-world security threats
• Potential for ongoing work and contract extension as recent projects launch

📌 Offensive Security Analyst (Canada)
🏢 Alignerr
📍 Canada