Open AI training and model evaluation roles that call for Vulnerability Assessment expertise, gathered from 4 platforms. Part of Data & Machine Learning.
Pay figures cover the 66 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 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.
An AI Red Team Analyst probes and stress-tests AI systems to identify security vulnerabilities, craft adversarial prompts, and evaluate model safety before bad actors can exploit them. This remote contract role suits security-minded professionals who combine cybersecurity expertise with hands-on experience testing large language models and AI systems.
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 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 security testing and red-teaming exercises on AI systems to identify vulnerabilities, weaknesses, and failure modes. The position is designed for security professionals who can think like attackers and use creative methods to stress-test AI models and evaluate their safety, bias, and policy compliance.
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 data security and Data Loss Prevention scenarios to help train AI models that understand real-world data risk. You will classify sensitive information, evaluate security strategies, and create labeled datasets for AI model development based on your hands-on security expertise.
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.
This fully remote freelance contract involves simulating attacks against web applications, internal and external networks, and cloud environments to find weaknesses before real adversaries do. It is aimed at experienced offensive security professionals who can manage engagements independently and explain their findings clearly to non-technical stakeholders. The role also includes recurring red-team and purple-team support alongside security operations teams.
This remote contract role asks analysts to bring offensive security knowledge to AI development without writing exploits or taking part in live intrusions. The work centers on analyzing attack paths and adversary behavior in structured scenarios, then producing labeled reasoning data and written assessments that help AI systems reason about cybersecurity. It suits experienced security professionals who can explain how real attacks unfold in production environments.
This contract role asks security-minded people to probe AI systems built on the OpenClaw platform by running red-teaming exercises and writing adversarial prompts. The work suits cybersecurity practitioners who enjoy finding weaknesses and who can document their findings clearly for technical and non-technical readers.
This contract role asks a senior cloud security expert to assess cloud architectures on AWS, Azure, and GCP for design weaknesses, IAM risks, and misconfigurations before they lead to breaches. The work is remote and hourly, with recurring assessments and reports that turn technical findings into prioritized mitigation guidance. It is aimed at experienced cloud security architects who can work on complex, large-scale environments.
This remote contract role asks security practitioners to assess and improve AI systems on cybersecurity reasoning. The work centers on judging vulnerability scenarios, severity and remediation choices so the AI reflects how security teams actually operate. It suits people with hands-on vulnerability management experience who can explain security decisions clearly in writing.
As an Application Security Engineer, you will evaluate how AI models reason about secure design and identify security vulnerabilities they miss, including architectural flaws, unsafe deserialization, and overly permissive access controls. You will threat-model systems, conduct security code reviews, and write clear guidance on secure design and vulnerability fixes.
Add your resume once. Every open job is scored against your profile, and we email you only when a strong match appears. Free.
FAQ
66 Vulnerability Assessment 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 66 open roles that publish an hourly rate in USD, pay runs from $15 to $250 per hour, with a median of $63. These are the rates the platforms publish, not a guarantee of income or hours.
Mercor (42), Alignerr (19), DataAnnotation (3) and micro1 (2). You apply on the platform itself, which handles screening, contracts and payment.
The most requested areas of expertise on these listings are Vulnerability Assessment, AI Evaluation, Red Teaming, Adversarial Testing, AI Safety. 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.
