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AI Evaluation Specialist | $26/hr Remote

AI Evaluation Specialist | $26/hr Remote

Remote

United states

$ 26 /hour

Freelance

13-02-2026

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Skills

Communication Test Risk Analysis

Job Specifications

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

Type: Hourly contract

Compensation: $26/hour

Location: Remote (USA & Mexico)

Commitment: 10–40 hours/week

Role Responsibilities

Red-team conversational AI systems using jailbreaks, prompt injections, misuse cases, bias exploitation, and multi-turn adversarial strategies.
Generate high-quality human data by annotating failures, classifying vulnerabilities, and flagging systemic risks.
Follow structured taxonomies, benchmarks, and testing playbooks to ensure consistency and coverage.
Document findings reproducibly through reports, datasets, and adversarial test cases.
Evaluate AI outputs across sensitive or high-risk scenarios in alignment with defined safety guidelines.

Requirements

Native-level fluency in both English and Spanish.
Prior experience in AI red teaming, adversarial AI testing, cybersecurity, or socio-technical risk analysis.
Strong analytical and adversarial thinking skills.
Ability to apply structured evaluation frameworks and benchmarks.
Excellent written communication and documentation skills.
Comfortable working independently in a remote, project-based environment.
Based in the USA or Mexico.

Application Process (Takes 20 Min)

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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