AI Red Teamer (Remote)

The role

You will stress-test large language models by designing creative, adversarial prompts to expose vulnerabilities. This work supports AI safety and model robustness across risk categories like content safety, cybersecurity, and regulatory compliance.

What you will do

• Craft creative prompts and multi-turn scenarios to stress-test AI guardrails
• Discover ways around safety filters, restrictions, and defenses using jailbreak, evasion, and prompt injection techniques
• Explore edge cases to provoke disallowed, harmful, or incorrect outputs
• Evaluate and score model responses against structured harm taxonomies and severity rubrics
• Document experiments clearly
• Review and refine adversarial prompts generated by other team members
• Contribute to harm taxonomy development, calibration exercises, and inter-rater reliability work
• Collaborate with engineers, data scientists, and researchers to share findings
• Work with potentially disturbing content on a regular basis
• Stay current on jailbreaks, attack methods, and evolving model behaviors

Required qualifications

• Strong hands-on experience using multiple LLMs (ChatGPT, Claude, Gemini, open-source models, etc.)
• Creative, adversarial problem-solving skills
• Clear and thoughtful written communication
• Strong ethical judgment and the ability to separate adversarial thinking from personal values
• Self-directed, collaborative, and comfortable in feedback-heavy environments
• Curiosity, persistence, and comfort with frequent failure in experimentation

Nice to have

• Familiarity with jailbreak or evasion techniques
• Familiarity with Python or other scripting languages
• Experience working with LLM APIs or evaluation tooling
• Comfort with structured data annotation and rubric-based scoring
• Prior work in trust and safety, content moderation, QA, or security research
• Subject matter expertise in any high-risk domain (cybersecurity, chemistry, biology, medicine, law, finance, etc.)

Before you apply

• We are unable to hire candidates residing in California for this role

About the company

Handshake AI partners with leading AI research labs to make models safer and more robust. Their red teaming operations help identify vulnerabilities before they reach users.