Cybersecurity Expert — Earn $100/hr Training AI

Offensive Cybersecurity Expertise Sought for AI Training Earn up to $100/hr training AI with your offensive security expertise. OSCP-level pros needed for red team, pentest & IaC work at Outlier AI. Apply now. Cybersecurity Expert — Earn $100/hr Training AI | Outlier Apply Now Apply in minutes, work remotely on your own schedule, and earn up to $100/hr putting your offensive security expertise to work shaping AI See Common Tasks Work Remotely Up to $100 USD/hr Contribute to real AI research PhD PAY RATE LOCATION United States DEGREE REQ. Masters Earn Up to $100 USD/hr - Plus additional incentives Rates vary based on expertise and project requirements. Paid via PayPal and AirTM Remote - United States Choose your own schedule. Most experts spend 5-10 hrs/week, up to 40 hours Use GPT, Claude, and more — completely free Over $200/month in AI access, included at no extra cost. About the Role Responsibilities Ideal Qualification Compensation Application Process FAQs Outlier is the world's leading expert platform, connecting an elite network of contributors to train AI for OpenAI, Meta, and Microsoft — ensuring the AI shaping medicine is built by the people who understand it best. 900K+ Outlier Experts $600M+ Paid Out Countries Responsibilites Designing Capture-the-Flag-style attack environments spanning network, web-app, cloud, and Active Directory attack surfaces Deploying and automating those environments as infrastructure-as-code using Terraform and Ansible, so each scenario is reproducible and version-controlled Crafting realistic attack chains (initial access, privilege escalation, lateral movement, exfiltration) and evaluating AI-generated attempts to exploit them Authoring rubrics that distinguish authentic offensive-security judgment from tool-output or certification-exam-level recall Common Tasks Write a prompt Write simple prompts that will act as a starting point for AI models Edit Preview Correct AI-models chain of thought Review, analyze, and rank AI-models chains of thought for correctness and approach Step 1 Response Step 2 Response Improve Approve Step 3 Response 4+ years of hands-on professional experience in penetration testing, red teaming, or offensive security OSCP strongly preferred; other OSCP-class certifications also count (OSEP/OSWE, GPEN/GXPN, PNPT, CRTO, eCPPT, HTB CPTS) Hands-on infrastructure-as-code experience with Terraform and/or Ansible Ability to write clearly about offensive-security concepts in fluent English Currently accepting applicants from: Australia Canada New Zealand United Kingdom On average, contributors earn an additional 7.5% through Missions — Outlier's version of surge pricing. The top quartile boosts their earnings by an average of 11%. ** Join a Network of Elite Medical Professionals Work flexibly from anywhere, anytime - no minimum hours Free access to leading LLMs — worth $200+/month Create an account on Outlier Upload your resume and tell us about your background Upload your valid ID and add your phone number Start earning by completing tasks Frequently Asked Questions (FAQs) What is Outlier? How is it related to Scale AI? What's the expected time commitment for participants? When and how will I be paid? How can I get support? Who do I contact with questions as I onboard? What do I need to sign up for this opportunity? Will I be an Outlier employee? Who else will be a part of the program? Have more questions? View more FAQs here ** Rates vary based on expertise, skills assessment, location, project need, and other factors. For example, higher rates may be offered to PhDs. For non-core work, such as during initial project onboarding or project overtime phases, lower rates apply. Additional incentives data is based on payments made in the past six months and is updated quarterly. Certain projects offer incentive payments. Please review the payment terms for each project. PLEASE NOTE: We collect, retain and use personal data for our professional business purposes, including notifying you of opportunities that may be of interest and sharing with our affiliates. We limit the personal data we collect to that which we believe is appropriate and necessary to manage applicants’ needs, provide our services, and comply with applicable laws. Any information we collect in connection with your application will be treated in accordance with the Outlier Privacy Policy and our internal policies and programs designed to protect personal data. This is a 1099 contract opportunity on the Outlier.ai platform. Because this is a freelance opportunity, we do not offer internships, sponsorship, or employment. You must be authorized to work in your country of residence. If you are an international student, you may be able to sign up for Outlier if you are on a visa. You should contact your tax and/or immigration advisor with specific questions regarding your circumstances. Ready to use your brilliance to outsmart AI? in collaboration with Scale AI © 2026 Outlier. All rights reserved.