Crossing Hurdles logo

AI Penetration Tester | $111/hr Remote

Crossing Hurdles United States

remotecontract
Posted Oct 13, 2025

At Crossing Hurdles, we work as a referral partner. We refer candidates to our partner that collaborates with world’s leading AI research labs to build and train cutting-edge AI models.

Position: AI Red-Teamer — Adversarial AI Testing (Advanced)

Type: Hourly Contract Compensatio

Full Description

At Crossing Hurdles, we work as a referral partner. We refer candidates to our partner that collaborates with world’s leading AI research labs to build and train cutting-edge AI models.

Position: AI Red-Teamer — Adversarial AI Testing (Advanced)

Type: Hourly Contract

Compensation: $54–$111/hour

Location: Remote

Duration: Full-time or part-time, flexible

Commitment: Flexible, asynchronous scheduling

Key Responsibilities Red-team AI models and agents by crafting jailbreaks, prompt injections, misuse cases, and exploit scenarios

Generate high-quality human data: annotate AI failures, classify vulnerabilities, and flag systemic risks Apply structured approaches using taxonomies, benchmarks, and playbooks to maintain consistency in testing Document findings comprehensively to produce reproducible reports, datasets, and attack cases Flexibly support multiple projects including LLM jailbreaks and socio-technical abuse testing across different customers

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

Application process: (Takes 20 min) Upload resume AI interview based on your resume (15 min) Submit form Show more Show less

Cookies & analytics consent

We serve candidates globally, so we only activate Google Tag Manager and other analytics after you opt in. This keeps us aligned with GDPR/UK DPA, ePrivacy, LGPD, and similar rules. Essential features still run without analytics cookies.

Read how we use data in our Privacy Policy and Terms of Service.