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 contemporary 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 new projects launch

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