AI Penetration Testing Expert

The work

Test AI applications, APIs, and infrastructure for exploitable weaknesses, then document evidence and remediation recommendations. This remote hourly contract requires 10 to 40 hours per week and draws on practical offensive security experience.

Responsibilities

• Carry out penetration assessments of AI applications, interfaces, and supporting infrastructure.
• Investigate weaknesses in AI and machine learning pipelines, including prompt injection, model manipulation, poisoning risks, and authentication problems.
• Assess web, network, and API security with established tools and methods.
• Model attack sequences from reconnaissance through exploitation and activity after initial access.
• Produce reports that explain evidence, severity, and practical remediation options.
• Examine adversarial inputs, attempts to bypass safeguards, and risks of data leaving the system.
• Track emerging AI threats and contribute findings that improve the testing approach.

Background and skills

You need professional penetration testing experience and strong knowledge of offensive methods, including OWASP, PTES, and MITRE ATT&CK. Fluency with tools such as Burp Suite, Metasploit, Nmap, Kali Linux, or comparable software is required.

Your background should cover web applications, networks, and API security. Creative, persistent, systematic investigation and the ability to explain technical findings in clear reports are essential. You must work reliably without direct supervision across varied technology stacks.

Additional strengths

Useful certifications include OSCP, OSCE, CEH, GPEN, GXPN, and eWPT. Other helpful experience includes adversarial machine learning, prompt injection, LLM security reviews, red teaming, bug bounties, or CTF competitions.

Cloud security in AWS, GCP, or Azure, container security, scripting in Python, Bash, or PowerShell, secure development, and DevSecOps are welcome. Assessments in environments governed by SOC 2, ISO 27001, or similar requirements are also useful.

Working arrangements

This is a remote hourly contract with 10 to 40 hours per week. Work is organized around independent assignments and a flexible schedule. Tasks can be completed on your own schedule.

Work with research teams may continue through further projects or contract extensions as new engagements begin.