AI Penetration Tester

Position Overview

The AI Penetration Tester at Crossing Hurdles will collaborate with world-leading AI research labs to red-team AI models by designing and executing adversarial testing strategies. This hourly contract position offers flexible full-time or part-time engagement, with asynchronous scheduling.

Key Responsibilities

• Red-team AI models and agents via jailbreaks, prompt injections, misuse cases, and exploit scenarios.
• Generate high-quality human data by annotating AI failures, classifying vulnerabilities, and flagging systemic risks.
• Apply structured approaches using taxonomies, benchmarks, and playbooks to standardize testing.
• Document findings comprehensively to produce reproducible reports, datasets, and attack cases.
• Support multiple projects including LLM jailbreaks and socio-technical abuse testing across various customers.

Required Qualifications

• Prior red-teaming experience in adversarial AI testing, cybersecurity, or socio-technical probing OR a strong AI background enabling rapid learning.
• Expertise in adversarial machine learning including jailbreak datasets, prompt injection, RLHF/DPO attacks, and model extraction.
• Cybersecurity skills such as penetration testing, exploit development, and reverse engineering.
• Experience with socio-technical risk areas like harassment, disinformation, or abuse analysis.
• Creative probing skills using psychology, acting, or writing to develop unconventional adversarial methods.

Application Process

The process takes 20 minutes: upload your resume, complete an AI interview based on your resume (15 minutes), and submit a form.

Key skills/competency

• Adversarial AI
• Penetration Testing
• Cybersecurity
• AI Red-Teaming
• Jailbreak Techniques
• Prompt Injection
• Model Extraction
• Risk Analysis
• Data Annotation
• Exploit Development