Cybersecurity Penetration Testing Expert (AI Security)

Before Applying

This role is open to contractors in accepted locations only. Please confirm your country is on the list before applying — we're unable to process applications from unlisted locations. List of accepted countries and locations.

For US applicants This is a 1099 independent contractor role. It is not compatible with F-1 OPT, STEM OPT, or any visa status that requires W-2 employment, guaranteed hours, or employer sponsorship. We are unable to provide offer letters or employment verification for this role.

What You'll Be Doing

Probe and stress-test AI-powered applications, APIs, and supporting infrastructure to surface vulnerabilities before attackers do:

• Run penetration tests against AI apps, APIs, and infrastructure — reconnaissance through exploitation and post-exploitation
• Hunt AI/ML-specific attack surfaces — prompt injection, jailbreaks, model manipulation, data poisoning, adversarial inputs, and data exfiltration vectors
• Perform web application, network, and API security assessments using industry-standard methodologies (OWASP, PTES, MITRE ATT&CK)
• Document findings in clear, structured reports with severity ratings, reproductions, and actionable remediation

End result: AI systems that hold up against real adversaries, with vulnerabilities surfaced and fixed before they reach production.

AI red-teaming in one line: Probe → exploit → document with reproductions → feed findings into hardening cycles → models and infrastructure that withstand real-world attacks.

What You'll Need

• 3+ years of professional penetration testing or offensive security experience covering web applications, networks, and APIs (OSCP, OSCE, GPEN, GXPN, or eWPT certification is a bonus, but not required)
• Strong attacker mindset — you can spot logic flaws, auth bypasses, injection vectors, and exploit chaining opportunities quickly
• Proficiency with industry-standard tools such as Burp Suite, Metasploit, Nmap, Kali Linux, or equivalents
• Extreme attention to detail and excellent written communication skills. Much of this role involves explaining what you found, how you found it, and how to fix it. This cannot be overstated.
• Comfortable reading documentation, security advisories, and source code, and able to work well in an asynchronous, low-oversight environment

Identity verification: Applicants will be required to verify their identity and confirm they have valid documentation to work as an independent contractor in their country of residence.

What You Don't Need

• No prior AI/ML security testing experience. If you can pentest a web app, API, or network, the AI-specific attack surfaces — prompt injection, jailbreaks, adversarial inputs — are learnable on the job.

Logistics

• Location: Fully remote — work from anywhere on the accepted locations list
• Compensation: $60–$120/hr based on location and seniority.
• Hours: Minimum 10 hrs/week, up to 40+ hrs/week available — hours vary by project and are not guaranteed week to week
• Engagement: 1099 independent contractor
• Payment: Weekly via PayPal or Stripe

⚠️ Important: Hours are project-dependent and can vary week to week. We recommend keeping other work options open alongside this engagement rather than relying on it as your sole source of income.