AI Red Teamer (LLM Generalist) - Remote

Apply; Northern (KY); Hybrid; USD 120,000 - 180,000; Part time

Job summary

Handshake AI seeks an AI Red Teamer to stress-test large language models by crafting adversarial prompts that reveal vulnerabilities in safety guardrails, bias, and jailbreaking weaknesses. This role covers multiple risk areas including content safety, cybersecurity, and high-risk domains, across text, image, and agentic capabilities.

You will work with engineers and researchers to document experiments, score outputs against harm taxonomies, and help strengthen defenses while operating with

Qualifications

• Stress-test AI models by crafting creative adversarial prompts.
• Evaluate model outputs against harm taxonomies and severity rubrics.
• Document experiments with methods and findings.
• Collaborate with engineers and researchers to strengthen defenses.

Responsibilities

• Craft prompts and multi-turn scenarios to stress-test AI guardrails across diverse risk categories.
• Discover jailbreak, evasion, and prompt-injection techniques.
• Explore edge cases to provoke disallowed or harmful outputs.
• Evaluate and score model responses using structured harm taxonomies.

Skills

LLM experience

Adversarial prompts

Creative problem-solving

Written communication

Ethical judgment

Self-directed

Curiosity

Python basics

LLM APIs

Data annotation

Trust and safety

Subject matter expertise

Tools

Python

Job description

AI Red Teamer (LLM Generalist)

Location: Remote (USA)
Type: Contract, 40 hours per week

About the Role

As an AI Red Teamer, you will stress-test large language models by intentionally trying to break them. Rather than checking whether an answer is correct, you will design creative, adversarial prompts that expose vulnerabilities: unsafe content, bias, broken guardrails, hallucinations, prompt injection weaknesses, and unexpected behaviors. Your work directly supports AI safety and model robustness for leading research labs.

This is a generalist red teaming role. You will probe models across the full spectrum of risk categories, including content safety, CBRN (chemical, biological, radiological, nuclear), cybersecurity, persuasion and influence operations, child safety, self-harm, over-companionship, and regulatory compliance. Red teaming may span text, image, voice, and agentic model capabilities depending on project needs.

This role requires creativity, curiosity, and an ability to think like an adversary while operating with strong ethical judgment.

Day-to-Day Responsibilities

• 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

Core

• 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

Nice to Have

• 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.)

You Will Thrive Here If

• 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.

About Handshake AI

Handshake AI partners with leading AI research labs to make models safer and more robust. Our red teaming operations help identify vulnerabilities before they reach users, contributing directly to the responsible development of frontier AI systems.

California eligibility: We are unable to hire candidates residing in California for this role.