AI Red Team — Penetration Testing Expert

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

Job summary

Alignerr is seeking Penetration Testing Experts to join AI red team engagements—probing and stress-testing AI-powered applications to identify vulnerabilities before bad actors. This is a fully remote hourly contract with 10-40 hours per week, offering flexible scheduling.

You will conduct tests across applications, APIs, and infrastructure, exploit AI/ML weaknesses, produce clear reports, and stay ahead of emerging AI threats while working independently.

Qualifications

• Minimum experience in penetration testing with offensive security practices.
• Ability to document findings clearly with remediation guidance.
• Familiarity with OWASP/ATT&CK frameworks.
• Comfort working remotely on flexible schedules.

Responsibilities

• Conduct penetration tests on AI-powered apps, APIs, and infrastructure.
• Exploit weaknesses in AI/ML pipelines including prompt injection.
• Perform web, network, and API security assessments with standard tools.
• Simulate reconnaissance through exploitation and post-exploitation.
• Document findings with severity ratings and remediation guidance.
• Evaluate AI-specific attack surfaces like adversarial inputs and data exfiltration.
• Stay updated on AI security threats and contribute to testing methods.
• Work independently on task-based engagements with flexible scheduling.

Skills

Penetration testing

Offensive security

OWASP/PTES/ATT&CK

Report writing

Tools

Burp Suite

Metasploit

Nmap

Kali Linux

Job description

About The Role

What if your hacking skills could directly shape how safe and secure AI systems are for millions of users worldwide? We're looking for Penetration Testing Experts to join AI red team engagements - probing, attacking, and stress-testing AI-powered applications and infrastructure to identify vulnerabilities before bad actors do.

About The Role

What if your hacking skills could directly shape how safe and secure AI systems are for millions of users worldwide? We're looking for Penetration Testing Experts to join AI red team engagements - probing, attacking, and stress-testing AI-powered applications and infrastructure to identify vulnerabilities before bad actors do. This is a fully remote, flexible contract role where your offensive security expertise meets the cutting edge of artificial intelligence. You'll work on high-impact projects that directly improve the security posture of AI systems used at scale.

• Organization: Alignerr
• Type: Hourly Contract
• Location: Remote
• Commitment: 10-40 hours/week

What You'll Do

• Conduct penetration tests against AI-powered applications, APIs, and infrastructure to uncover security vulnerabilities
• Identify and exploit weaknesses in AI/ML pipelines, including prompt injection, model manipulation, data poisoning vectors, and authentication flaws
• Perform web application, network, and API security assessments using industry-standard tools and methodologies
• Simulate real-world attack scenarios - from reconnaissance through exploitation and post-exploitation
• Document findings in clear, structured reports with severity ratings, evidence, and actionable remediation guidance
• Evaluate AI-specific attack surfaces including adversarial inputs, jailbreaks, and data exfiltration risks
• Stay current with emerging AI security threats and contribute insights to improve testing methodologies
• Work independently on task-based engagements on your own schedule

Who You Are

• Experienced penetration tester with a strong understanding of offensive security principles and methodologies (OWASP, PTES, MITRE ATT&CK)
• Proficient with industry-standard tools such as Burp Suite, Metasploit, Nmap, Kali Linux, or equivalent
• Solid understanding of web application security, network security, and API security testing
• Able to think like an attacker - creative, persistent, and methodical in finding what others miss
• Strong written communication skills - you can translate complex technical findings into clear, actionable reports
• Self-motivated and reliable when working independently without direct supervision
• Comfortable working across diverse technology stacks and environments

Nice to Have

• Relevant certifications such as OSCP, OSCE, CEH, GPEN, GXPN, or eWPT
• Experience with AI/ML security testing - adversarial machine learning, prompt injection, LLM red-teaming
• Background in red teaming, bug bounty programs, or CTF competitions
• Familiarity with cloud security (AWS, GCP, Azure) and container security
• Programming or scripting skills in Python, Bash, PowerShell, or similar
• Knowledge of secure development practices and DevSecOps workflows
• Experience conducting security assessments in compliance-driven environments (SOC 2, ISO 27001, etc.)

Why Join Us

• Work on cutting-edge AI security projects alongside leading research labs
• Fully remote and flexible - work when and where it suits you
• Freelance autonomy with access to high-impact, intellectually challenging engagements
• Be at the forefront of AI security - a rapidly growing field with massive demand
• Sharpen your skills against novel AI-specific attack surfaces that few security professionals have encountered
• Contribute directly to making AI systems safer and more trustworthy for users worldwide
• Potential for ongoing work and contract extension as new projects launch