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AI Red-Teamer - Adversarial AI Testing English at Weekday AI. This role is for one of our clients. Compensation: $50-$111 per hour. We are seeking . AI Red-Teamers. to help test and strengthen modern AI systems through adversarial evaluation. In this role, you will challenge AI models with carefully designed inputs to uncover weaknesses, surface vulnerabilities, and generate high-quality data that improves the safety, reliability, and robustness of conversational AI.. This work focuses on proactively identifying potential risks before they appear in real-world use. By systematically probing AI systems, you will help ensure they respond safely, accurately, and responsibly across a wide range of scenarios.. This role may include reviewing AI outputs that reference . sensitive topics such as bias, misinformation, or harmful behaviors. . All work is text-based, and participation in higher-sensitivity projects is optional and supported with clear guidelines and wellness resources.. What You’ll Do. . Red-team AI models and agents. by testing jailbreak attempts, prompt injections, misuse scenarios, and exploit strategies . . Generate high-quality human evaluation data. by annotating model failures, classifying vulnerabilities, and identifying systemic risks . . Apply structured testing methodologies. using taxonomies, benchmarks, and playbooks to ensure consistent evaluation . . Document findings clearly and reproducibly. , producing reports, datasets, and adversarial test cases that teams can act upon . . Work across multiple projects. , supporting different AI systems and evaluation objectives . Who You Are. You have . prior red-teaming experience. , such as adversarial AI testing, cybersecurity, or socio-technical risk analysis . You naturally think . adversarially. , exploring ways to push systems to their limits and uncover weaknesses . You prefer . structured methodologies. , using frameworks and benchmarks rather than ad-hoc testing . You communicate risks and vulnerabilities . clearly to both technical and non-technical audiences. . You are comfortable . working across multiple projects and adapting to new evaluation challenges. . Nice-to-Have Specialties. . Adversarial Machine Learning:. jailbreak datasets, prompt injection attacks, RLHF/DPO vulnerabilities, or model extraction techniques . . Cybersecurity:. penetration testing, exploit development, reverse engineering . . Socio-technical risk analysis:. harassment or misinformation testing, abuse pattern analysis . . Creative adversarial thinking:. backgrounds in psychology, acting, writing, or other disciplines that support unconventional attack strategies . What Success Looks Like. You uncover vulnerabilities and failure modes that automated tests miss . Your work produces . reproducible artifacts and datasets. that improve AI system resilience . Evaluation coverage expands with . more realistic adversarial scenarios tested before deployment. . AI systems become . safer and more reliable. due to your rigorous testing and insights . Why Join. Contribute directly to . frontier work in AI safety and adversarial testing. . Help improve the . robustness, safety, and trustworthiness of modern AI systems. . Gain hands-on experience working with . human data-driven AI evaluation methodologies. . Compensation may vary depending on the . project, customer requirements, level of expertise, and content sensitivity. involved in each engagement.. Contract and Payment Terms. Engagement will be as an . independent contractor. . This is a . fully remote role. that can be completed on your own schedule . Projects may be . extended, shortened, or concluded early. depending on project needs and performance . Work performed will . not involve access to confidential or proprietary information. from any employer, client, or institution . . Payments are issued weekly. via . Stripe or Wise. based on services rendered . Please note: . Candidates requiring H1-B or STEM OPT sponsorship cannot be supported for this role at this time.. Company Location: Canada.