> Markdown version of [/jobs/ext/1486486-penetration-testing-ai-evaluator](https://www.wearedevelopers.com/jobs/ext/1486486-penetration-testing-ai-evaluator). Every page supports `.md` or `Accept: text/markdown`. Links point to the HTML versions so they work for humans too. Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Penetration Testing AI Evaluator - **Company:** Human Union Data, Inc. - **Location:** United States (Remote available) - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Software System Penetration Testing, Cyber Security - **Published:** July 29, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=d58e5bb43c4f95ab ## About the Role * Prior evaluation, annotation, or human-rater experience on penetration testing ai evaluation or adjacent content for Penetration Testing AI Evaluator work. * Comfort applying multi-page rubrics consistently across long batches. * Clear written reasoning that names the issue and the rubric clause being applied. * Strong attention to detail and the ability to flag when a prompt itself is the problem. * Reliable async availability for at least 10 hours per week., * Background in linguistics, content moderation, or trust & safety review. * Experience with inter-rater agreement metrics and calibration cycles. * Domain expertise that lets you spot subject-matter errors automated checks miss., * Model output evaluation * Rubric-based annotation * Severity tagging * Inter-rater calibration * Penetration Testing AI evaluation * Cybersecurity * AI evaluation * Rubric writing * Expert review Work model Remote - US-eligible. Remote ยท Independent specialist contractor. Employment type: CONTRACTOR. Applicants must be authorized to work from US. ## Description Penetration Testing AI Evaluator is a remote evaluation track for reviewing penetration testing ai evaluation prompts and responses against AuraOne's quality rubric. Reviewers compare paired outputs, label edge cases, and write the kind of structured feedback the modeling team can use to retrain. Why this role matters AI data reviewers help turn penetration testing ai evaluation outputs into auditable labels, rationales, and regression cases for AuraOne Human Data., * Evaluate penetration testing ai evaluation model outputs against a versioned rubric and assign severity tags for Penetration Testing AI Evaluator assignments. * Compare paired responses and pick the stronger answer with a written rationale. * Label hallucinations, instruction-following failures, and unsafe content with structured tags. * Capture ambiguous prompts and route them back to the program team for rubric updates. * Maintain reviewer-quality scores by calibrating against gold-standard examples each week. * Document recurring failure modes so the modeling team can target them in the next training run., * Tag an unsafe response with the correct policy category and severity. * Audit a 50-row batch for rubric consistency and report drift to the program lead. * Propose a rubric clarification after spotting a recurring failure mode. ## Related Videos - [Thinking Differently - How to Make Money from Cyber Attacks & Cheats](https://www.wearedevelopers.com/videos/745-thinking-differently-how-to-make-money-from-cyber-attacks-cheats) - [Edit Your Future: Queerverse Radical AI](https://www.wearedevelopers.com/videos/909-edit-your-future-queerverse-radical-ai) - [Hacking Kubernetes: Live Demo Marathon](https://www.wearedevelopers.com/videos/488-hacking-kubernetes-live-demo-marathon) - [How to Assess and Hire Talent: The Skills-Based Hiring Playbook for the AI Age](https://www.wearedevelopers.com/videos/1488-how-to-assess-and-hire-talent-the-skills-based-hiring-playbook-for-the-ai-age) - [Building Trustworthy AI in Industry: Beyond Traditional Cybersecurity](https://www.wearedevelopers.com/videos/1948-building-trustworthy-ai-in-industry-beyond-traditional-cybersecurity) - [Cyber Security: Small, and Large!](https://www.wearedevelopers.com/videos/259-cyber-security-small-and-large) ## Related Articles - [Dev Digest 134 - Where pixels sing?](https://www.wearedevelopers.com/magazine/477-dev-digest-134-where-pixels-sing) - [13 AI Tools You Have to Try](https://www.wearedevelopers.com/magazine/219-13-ai-tools-you-have-to-try) - [Dev Digest 121 - AI goes offline](https://www.wearedevelopers.com/magazine/456-dev-digest-121-ai-goes-offline) - [13 AI Tools for Developers](https://www.wearedevelopers.com/magazine/302-13-ai-tools-for-developers) - [Dev Digest 137 - AI'm not sure about this](https://www.wearedevelopers.com/magazine/485-dev-digest-137-ai-m-not-sure-about-this) - [Prompt Engineering is a Job of the Past](https://www.wearedevelopers.com/magazine/342-prompt-engineering-is-a-job-of-the-past)