Skills

Penetration Testing Risk Analysis Machine Learning

Job Specifications

Position: AI Red-Teamer — Adversarial AI Testing (Advanced); English & Japanese

Type: Hourly contract

Compensation: $50.5 per hour

Location: Remote

Commitment: 10–40 hours/week

Role Responsibilities

Red team conversational AI models and agents, including jailbreaks, prompt injections, misuse cases, bias exploitation, and multi-turn manipulation
Generate high-quality human data by annotating failures, classifying vulnerabilities, and flagging systemic risks
Apply testing structure by following taxonomies, benchmarks, and playbooks to keep evaluations consistent
Produce reproducible documentation, including reports, datasets, and attack cases that customers can act on

Requirements

Prior red teaming experience in areas such as AI adversarial work, cybersecurity, or socio-technical probing
Native-level fluency in English and Japanese
Strong adversarial mindset with the ability to push systems to their limits to uncover vulnerabilities
Ability to use structured frameworks or benchmarks rather than ad-hoc testing approaches
Ability to clearly communicate risks to both technical and non-technical stakeholders
Ability to adapt and move across different projects and customers
Experience with adversarial machine learning techniques such as jailbreak datasets, prompt injection, RLHF or DPO attacks, and model extraction
Experience in cybersecurity, including penetration testing, exploit development, or reverse engineering
Experience with socio-technical risk analysis, including harassment or misinformation probing, abuse analysis, and conversational AI testing
Creative or unconventional adversarial thinking, such as psychology, acting, or writing for creative probing

Application Process (Takes 20 Mins)

Upload resume
Interview (15 min)
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About the Company

At Crossing Hurdles, we specialise in customised recruitment and staffing solutions designed to drive success for businesses and professionals. Our focus is on connecting organisations with top-tier talent by sourcing, screening, and presenting only the top 1% of candidates across a wide range of industries. We work closely with clients to understand their unique needs, ensuring that we find candidates who not only fit the role but also align with their organizational culture. Over the past few quarters, we've successfully p... Know more