About The Role What if your hard-won knowledge of how attackers think, move, and succeed could directly shape the AI systems that millions of people will rely on to stay secure? We're looking for Offensive Security Analysts to bring real-world adversarial thinking to frontier AI development. This isn't a traditional red team gig — there's no exploit development, no active intrusion, and no CVE hunting.

Instead, you'll apply your deep understanding of attack paths, kill chains, and adversary behavior to help train and evaluate AI systems that reason about cybersecurity at a high level. This is a fully remote, flexible contract role. If you think like an attacker and can articulate how threats unfold in production environments, we want to hear from you.

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 systems and environments

Identify and classify weaknesses, misconfigurations, and defensive gaps in structured scenarios

Review red-team-style narratives and intrusion scenarios for accuracy, realism, and completeness

Generate, label, and validate adversarial reasoning data used to train and evaluate AI models

Clearly articulate attack chains, business impact, and security tradeoffs in written form





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 in production environments — not just in theory

You can break down a complex attack chain and explain it clearly to a technical audience

You think in terms of attacker objectives, not just individual techniques

Naturally detail-oriented with a structured, methodical approach to analysis

Comfortable producing written assessments and structured data outputs Nice to Have Familiarity with frameworks like MITRE ATT&CK;, Cyber Kill Chain, or STRIDE

Experience writing threat models, attack narratives, or red team reports

Background in threat intelligence, security architecture review, or purple teaming

Exposure to cloud, OT/ICS, or enterprise network environments

Prior experience contributing to AI or data labeling projects 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 genuinely novel and high-impact problem space

Potential for ongoing work and contract extension as recent projects launch

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