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Crossing Hurdles
Cyber Security Specialist | Remote

Cyber Security Specialist | Remote

Remote

Canada

$ 111 /hour

Freelance

09-02-2026

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Skills

Communication Test Risk Analysis

Job Specifications

Position: AI Red-Teamer — Adversarial AI Testing; English

Type: Hourly contract

Compensation: $50–$111 per hour

Location: Remote

Commitment: Full-time or part-time, flexible project-based engagement

Role Responsibilities

Conduct adversarial testing of AI models, including jailbreaks, prompt injections, misuse cases, and exploit discovery
Generate high-quality human evaluation data by annotating failures, classifying vulnerabilities, and flagging systemic risks
Apply structured red-teaming frameworks, taxonomies, benchmarks, and playbooks to ensure consistent testing
Produce clear, reproducible documentation such as reports, datasets, and adversarial test cases
Support multiple customer projects, ranging from LLM safety testing to socio-technical abuse and misuse analysis
Communicate identified risks and vulnerabilities clearly to technical and non-technical stakeholders

Requirements

Strong experience in AI red-teaming, adversarial testing, cybersecurity, or socio-technical risk analysis
Strong ability to probe systems creatively and systematically to uncover failure modes
Strong experience using structured evaluation frameworks rather than ad-hoc testing
Strong written communication skills with the ability to clearly document risks and findings
Comfort working across sensitive content areas such as bias, misinformation, or harmful behaviors
Ability to work independently in a remote, fast-moving project environment

Application Process (Takes 20 Mins)

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Complete an interview.
Submit a short form.

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