handshake - AI Red Teamer (Remote)

• Craft creative prompts and multi-turn scenarios to stress-test AI guardrails across diverse risk categories • 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, including what you tried, why you tried it, and what it revealed • 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 and strengthen defenses • Work with potentially disturbing content on a regular basis (see Content Warning below) • Stay current on jailbreaks, attack methods, and evolving model behaviors • DESIRED CAPABILITIES • Strong hands-on experience using multiple LLMs (ChatGPT, Claude, Gemini, open-source models, etc.) • Intuition for crafting adversarial prompts; familiarity with jailbreak or evasion techniques is a strong plus • 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 • You treat every model response as a hypothesis to challenge • You can switch between creative free-association and rigorous documentation in the same session • You go deep into unusual interests (fandoms, niche internet cultures, gaming exploits, Wikipedia rabbit holes, etc.) • You come from a creative background: writing, visual art, improv, puzzle design, or similar • You are energized by finding the thing nobody else thought to try • You are genuinely passionate about AI and follow the space closely • CONTENT WARNING • This role involves regular and deliberate exposure to harmful content. You will encounter and intentionally generate content involving violence, self-harm, hate speech, sexually explicit material, child safety scenarios, and other categories of harmful output as part of structured adversarial testing. Candidates must be able to engage with this material professionally and sustainably. Support resources are available.