About the Role
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
52
Countries
Responsibilites
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
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
Ideal Qualification
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
🇺🇸
United States
Compensation
Work flexibly from anywhere, anytime - no minimum hours
Application Process
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?
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What do I need to sign up for this opportunity?
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** 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.
