AI Red Team — Penetration Testing Expert

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

Conduct penetration tests and red team engagements against AI-powered applications and infrastructure to identify security vulnerabilities. Document findings in structured reports with severity ratings and provide actionable remediation guidance.

Requires an experienced penetration tester proficient with industry-standard tools and offensive security methodologies like OWASP and MITRE ATT&CK. Candidates should have a strong ability to simulate real-world attacks and translate technical findings into clear reports.

• PythonPreferred

Identified from the job description. Confirm important requirements above.

• Penetration Testing
• AI Red Teaming
• Offensive Security
• Prompt Injection
• Web Application Security
• API Security
• Network Security
• Adversarial Machine Learning
• Burp Suite
• Metasploit
• Kali Linux
• Python
• Cloud Security
• Vulnerability Assessment
• Report Writing
• OWASP

• Security & Safety
• Technology
• Software
• Engineering
• Consulting

Minimum education

Professional degree

Minimum experience

5+ years

Apply by

Sep 4, 2026

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Toronto, Ontario, Canada

Seniority

Mid-Senior level