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Cybersecurity Penetration Testing Expert (AI Security)

📍 Location
winnipeg
⏰ Job Type
Full-time
📅 Posted
June 03, 2026

About the Role

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 we...

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