Offensive Security Analyst (Structured / Non-Exploit)

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

Analyze attack paths and adversary strategies to generate and validate reasoning data for training AI models. Review red-team narratives and identify defensive gaps in structured scenarios to improve AI cybersecurity capabilities.

Requires 2+ years of hands-on experience in offensive or defensive security roles with a deep understanding of production environment attacks. Candidates must be able to articulate complex attack chains clearly in written form.

Identified from the job description. Confirm important requirements above.

• Pentesting
• Red Teaming
• Blue Teaming
• Adversarial Thinking
• Attack Path Analysis
• Kill Chain Analysis
• Threat Modeling
• Security Architecture Review
• Data Labeling
• Technical Writing
• MITRE ATT&CK
• STRIDE
• Cloud Security
• OT/ICS Security
• Enterprise Network Security
• Purple Teaming

• Security & Safety
• Technology
• Software
• Data & Analytics
• Consulting

Minimum experience

2+ years

Apply by

Aug 29, 2026

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Toronto, Ontario, Canada

Seniority

Entry level