Summary: This role involves red teaming conversational AI models, generating high-quality human data, applying structure, and documenting findings to enhance AI safety. Highlights: 1. Probe AI models with adversarial inputs to surface vulnerabilities 2. Generate red team data to make AI safer for customers 3. Opportunity to uncover vulnerabilities automated tests miss **Location**: Remote **Type**: Full\-time or Part\-time Contract Work **Fluent Language Skills Required:** English \& Italian. Native\-level fluency in English and Italian is required for this position. **Why This Role Exists** We believe the safest AI is the one that’s already been attacked , by us. We are assembling a red team for this project \- human data experts who probe AI models with adversarial inputs, surface vulnerabilities, and generate the red team data that makes AI safer for our customers. This project involves reviewing AI outputs that touch on sensitive topics such as bias, misinformation, or harmful behaviors. All work is text\-based, and participation in higher\-sensitivity projects is optional and supported by clear guidelines and wellness resources. Before being exposed to any content, the topics will be clearly communicated. **What You’ll Do** * Red team conversational AI models and agents: jailbreaks, prompt injections, misuse cases, bias exploitation, multi\-turn manipulation * Generate high\-quality human data: annotate failures, classify vulnerabilities, and flag systemic risks * Apply structure: follow taxonomies, benchmarks, and playbooks to keep testing consistent * Document reproducibly: produce reports, datasets, and attack cases customers can act on **Who You Are** * You bring prior red teaming experience (AI adversarial work, cybersecurity, socio\-technical probing) * You’re curious and adversarial: you instinctively push systems to breaking points * You’re structured: you use frameworks or benchmarks, not just random hacks * You’re communicative: you explain risks clearly to technical and non\-technical stakeholders * You’re adaptable: thrive on moving across projects and customers **Nice\-to\-Have Specialties** * Adversarial ML: jailbreak datasets, prompt injection, RLHF/DPO attacks, model extraction * Cybersecurity: penetration testing, exploit development, reverse engineering * Socio\-technical risk: harassment/disinfo probing, abuse analysis, conversational AI testing * Creative probing: psychology, acting, writing for unconventional adversarial thinking **What Success Looks Like** * You uncover vulnerabilities automated tests miss * You deliver reproducible artifacts that strengthen customer AI systems * Evaluation coverage expands: more scenarios tested, fewer surprises in production