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Adversarial Prompt Expert at Reinforce Labs, Inc.. Remote Location: Remote. We are looking for a creative "breaker" to join our team as an Adversarial Prompt Expert. In this role, you won’t just be using LLMs—you’ll be stress-testing their boundaries, bypassing their safeguards, and helping us build safer, more robust intelligence.. This is an . asynchronous, remote position. designed for self-starters who thrive in the gray areas between code, linguistics, and security.. Work Details. Design and execute complex jailbreak attempts to identify vulnerabilities in state-of-the-art models.. Use your background in linguistics or social sciences to find "hidden" biases or harms that standard automated filters miss.. Model Evaluation: Systematically rank LLM outputs to determine where safety guardrails are failing or succeeding.. Knowledge Loop: Document your "attack vectors" clearly to help our engineering teams patch vulnerabilities.. Who you Are. Heavy LLM Usage — hands-on experience with multiple models (open- and closed-source), comfort experimenting across systems and platforms.. You have a "hacker mindset." You enjoy the puzzle of finding edge cases and can think of ten different ways to ask a forbidden question.. You can turn a chaotic afternoon of prompt-hacking into a clean, actionable report.. You understand the weight of this work. You can handle sensitive or "dark" content professionally and stay within ethical boundaries.. Qualifications & Skill Requirements. Proven ability to navigate complex model restrictions using creative evasion techniques.. Background in offensive security or red teaming is a major plus.. You don't give up when a model says "I cannot fulfill this request." You find a new angle.