Open AI training and model evaluation roles that call for Cybersecurity expertise, gathered from 4 platforms. Part of Software Engineering.
Pay figures cover the 45 open jobs that publish an hourly rate in USD. They are published rates, not a guarantee of income. Last checked on October 8, 2026.
This role involves analyzing cyber attacks, adversary tactics, and exploitation chains to produce structured assessments that help AI systems understand cybersecurity threats better. It is designed for experienced offensive security professionals who can evaluate threat behaviors and translate complex technical findings into clear documentation.
This role involves analyzing security vulnerabilities and threat scenarios in AI systems and large language models to identify weaknesses and recommend mitigations. Security professionals will conduct adversarial testing, evaluate real-world attack scenarios, and provide structured feedback to improve AI safety and resilience.
An experienced penetration tester will conduct offensive security assessments against AI-powered applications, infrastructure, and machine learning pipelines to identify vulnerabilities including prompt injection, model manipulation, and data poisoning attacks. The role involves simulating real-world attack scenarios, documenting findings with remediation guidance, and evaluating AI-specific security risks in a fully remote, flexible contract engagement.
This role involves conducting penetration tests and security assessments on AI-powered applications, infrastructure, and machine learning pipelines to identify vulnerabilities and weaknesses before malicious actors exploit them. The position suits experienced offensive security professionals who can work independently on contract-based engagements to stress-test AI systems and document findings with clear remediation guidance.
Penetration testing experts are needed to identify security vulnerabilities in AI-powered applications and infrastructure through offensive security testing. This remote contract role combines traditional penetration testing methodologies with emerging AI-specific attack scenarios such as prompt injection and model manipulation.
Join an AI red team as a penetration testing expert to identify vulnerabilities in AI-powered applications and infrastructure through offensive security testing. This remote, flexible role involves conducting penetration tests, simulating attacks, and evaluating AI-specific security risks to help secure AI systems at scale.
This role involves red-teaming and security testing of AI models to identify vulnerabilities and safety issues before deployment. The position is ideal for cybersecurity professionals who want to apply adversarial thinking and penetration testing skills to AI systems used at scale.
This role focuses on stress-testing and securing AI models by identifying vulnerabilities through red-teaming and adversarial testing. The position suits cybersecurity professionals who want to apply penetration testing and ethical hacking expertise to emerging AI security challenges.
This role involves conducting penetration tests and security assessments on AI-powered applications, infrastructure, and ML pipelines to identify vulnerabilities and attack vectors. The position suits experienced offensive security professionals who want to work on cutting-edge AI security challenges while maintaining flexibility as an independent contractor.
This role involves conducting penetration tests and security assessments on AI-powered applications, infrastructure, and machine learning pipelines to identify vulnerabilities and attack vectors. The position is ideal for experienced offensive security professionals who want to apply their hacking expertise to emerging AI security challenges in a fully remote, flexible contract setting.
This role involves conducting security testing and red-teaming exercises on advanced AI models to identify vulnerabilities, design adversarial prompts, and evaluate safety failures. The specialist will document findings and collaborate with engineering teams to strengthen AI system resilience and reliability.
This role involves analyzing real-world application security scenarios and creating training datasets to teach AI models how to assess software vulnerabilities. You will evaluate code, APIs, and system behavior to distinguish genuinely exploitable risks from theoretical findings, providing structured analysis that helps frontier AI systems learn to reason about application security with the nuance of experienced engineers.
This role involves analyzing real-world cloud security scenarios to identify risks, misconfigurations, and failure patterns across AWS, GCP, and Azure. Contractors will evaluate AI-generated security reasoning and help create datasets for training AI models to better understand cloud infrastructure vulnerabilities and incidents.
This role involves evaluating and stress-testing AI-generated cybersecurity content to ensure accuracy and safety. Cybersecurity Defence Analysts review threat analyses, incident response plans, and defensive recommendations while identifying errors and dangerous hallucinations, helping ensure AI systems provide trustworthy security guidance.
This role involves evaluating and stress-testing AI-generated cybersecurity content to ensure accuracy and safety. Cybersecurity Defense Analysts will review threat analyses, incident response plans, and defensive strategies produced by AI systems, identifying errors and dangerous misconceptions while providing detailed feedback to improve AI security guidance.
This role involves evaluating and stress-testing AI-generated cybersecurity content to ensure accuracy and safety. Cybersecurity experts with hands-on defense experience will review threat analyses, incident response plans, and security recommendations, identifying errors and gaps that could lead to real harm in production environments.
This role involves conducting penetration tests and security assessments on AI-powered applications, infrastructure, and machine learning pipelines to identify vulnerabilities and attack vectors. You will probe for weaknesses including prompt injection, model manipulation, and data poisoning, then document findings with remediation guidance for a fully remote contract position.
This remote, freelance role asks compliance and risk specialists to help build and assess AI systems that reason about security governance. The work centers on checking security policies, controls, and audit documentation against established frameworks and writing precise feedback that teaches models the nuances of compliance logic. It suits experienced GRC, compliance, or information security professionals who can work independently on flexible hours.
This remote contract role asks an IAM specialist to review how users prove who they are and what they can access across different organizations. The work covers finding gaps in authentication and privilege setups, then writing clear, structured reports on the results. It suits experienced identity professionals who can work independently and explain complex permission structures in writing.
This remote contract role asks an IAM specialist to help train and evaluate AI systems on identity and access security problems. The work covers reviewing access control scenarios, spotting misconfigurations and attack paths, and writing structured feedback. It suits experienced identity security professionals who can explain how identity failures happen in real enterprise environments.
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FAQ
45 Cybersecurity AI training jobs are open on SideHustler today. Listings are rechecked against the official postings: the latest check on this list was on October 8, 2026.
Among the 45 open roles that publish an hourly rate in USD, pay runs from $15 to $250 per hour, with a median of $60. These are the rates the platforms publish, not a guarantee of income or hours.
Alignerr (31), Mercor (7), DataAnnotation (4) and micro1 (3). You apply on the platform itself, which handles screening, contracts and payment.
The most requested areas of expertise on these listings are Cybersecurity, AI Evaluation, Vulnerability Assessment, Red Teaming, Adversarial Testing. Each listing states its own requirements.
Apply now opens the official posting on the platform, where you complete the application. You need no account on SideHustler. To see which roles fit your background first, add your resume and every open job is scored against your profile.
