LLM Jailbreak Red Teamer

Pay: $55–100/hour

You'll systematically probe large language models to find inputs that cause them to bypass safety guidelines and produce harmful, disallowed, or policy-violating outputs. Your work involves crafting adversarial prompts across defined harm categories — including but not limited to dangerous instructions, deceptive content, and identity manipulation — then documenting exactly what worked, what the model produced, and why the response constitutes a policy violation. You won't be testing randomly; each session is scoped to specific harm categories and model behaviors as directed by the research team.

The workflow is structured: you'll receive a target model, a harm taxonomy, and a session goal. You'll then attempt multiple attack vectors per category — direct prompting, role-play framing, multi-turn escalation, encoding tricks, and others — logging each attempt with the full prompt, model response, and a severity rating. Successful jailbreaks get promoted to a verified findings database; failed attempts are still valuable and should be logged with notes on why they failed. Sessions typically run 2–3 hours with a defined scope.

The strongest candidates are people who think like adversaries — researchers, security professionals, former CTF competitors, or anyone who has spent time stress-testing systems. You should be methodical enough to document findings reproducibly and creative enough to try non-obvious attack angles. Familiarity with existing jailbreak literature (DAN prompts, prompt injection, etc.) is assumed. You won't be writing exploit code, but you will be thinking in the same mode.

Skills & requirements

• Adversarial prompt crafting
• Harm taxonomy classification
• Multi-turn attack strategies
• Structured vulnerability documentation
• Policy violation severity rating
• Jailbreak technique knowledge

Category: Red Teaming