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Adversarial Prompt Expert

Reinforce Labs Inc

United States Remote contract

Posted: February 9, 2026

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Quick Summary

Design and execute complex jailbreak attempts to identify vulnerabilities in state-of-the-art models.

Job Description

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.

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