Offensive Security Analyst (Structured / Non-Exploit)

Alignerr Corp.; Toronto; Remote; CAD 83,000 - 165,000; Full time

Job summary

Alignerr Corp. seeks an Offensive Security Analyst to apply adversarial thinking to frontier AI development. The role focuses on attack paths, kill chains, and adversary behavior to train and evaluate AI systems for cybersecurity reasoning.

This remote, hourly-contract position offers flexible hours and freelance autonomy. Ideal candidates bring 2+ years in pentesting/red-teaming or blue-team roles with deep offensive knowledge and the ability to clearly articulate complex attack sequences for a

Qualifications

• 2+ years of hands-on pentesting, red teaming, or blue-team work with offensive knowledge.
• Ability to clearly describe attack chains and attacker objectives to technical audiences.
• Experience producing structured security assessments and data outputs for AI/training purposes.
• Comfortable working as a freelance contractor with asynchronous work style.

Responsibilities

• 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 narratives for accuracy, realism and completeness.
• Generate, label, and validate adversarial reasoning data used to train AI models.
• Clearly articulate attack chains, business impact, and security tradeoffs in writing.
• Work independently and asynchronously on your own schedule.

Skills

Pentesting

Blue-team

Offensive security

Threat modeling

Tools

MITRE ATT&CK

Cyber Kill Chain

STRIDE

Job description

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?

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 new projects launch