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Crossing Hurdles - remotehey
Crossing Hurdles

Penetration Tester | Remote

canada / Posted
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Position: AI Red-Teamer — Adversarial AI Testing; English

Type: Hourly contract

Compensation: $50–$111 per hour

Location: Remote

Commitment: Full-time or part-time, flexible project-based engagement


Role Responsibilities

  • Conduct adversarial testing of AI models, including jailbreaks, prompt injections, misuse cases, and exploit discovery
  • Generate high-quality human evaluation data by annotating failures, classifying vulnerabilities, and flagging systemic risks
  • Apply structured red-teaming frameworks, taxonomies, benchmarks, and playbooks to ensure consistent testing
  • Produce clear, reproducible documentation such as reports, datasets, and adversarial test cases
  • Support multiple customer projects, ranging from LLM safety testing to socio-technical abuse and misuse analysis
  • Communicate identified risks and vulnerabilities clearly to technical and non-technical stakeholders


Requirements

  • Strong experience in AI red-teaming, adversarial testing, cybersecurity, or socio-technical risk analysis
  • Strong ability to probe systems creatively and systematically to uncover failure modes
  • Strong experience using structured evaluation frameworks rather than ad-hoc testing
  • Strong written communication skills with the ability to clearly document risks and findings
  • Comfort working across sensitive content areas such as bias, misinformation, or harmful behaviors
  • Ability to work independently in a remote, fast-moving project environment


Application Process (Takes 20 Mins)

  • Upload your resume.
  • Complete an interview.
  • Submit a short form.