Cybersecurity Penetration Testing Expert (AI Security)

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 Cybersecurity Penetration Testing Experts to probe, attack, and stress-test AI-powered applications and infrastructure — identifying 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