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

Solid 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 new projects launch

📌 Offensive Security Analyst (Structured / Non-Exploit) (Canada)
🏢 Alignerr
📍 Canada