Where
Australia, Canada, New Zealand, the United Kingdom and the United States, as named on the Outlier page.
Screening
Create an Outlier account, upload a résumé and a valid ID. The page looks for four or more years of hands-on penetration testing, red-teaming or offensive security, with OSCP strongly preferred, and infrastructure-as-code experience with Terraform and/or Ansible.
Role details
Outlier is seeking offensive cybersecurity experts to design realistic attack environments, evaluate AI-generated attempts, and tell authentic security reasoning apart from superficial recall. The listed pay is up to $70 USD an hour, plus additional incentives the page describes. Work is remote, with no minimum hours stated.
Responsibilities listed on the page include designing capture-the-flag-style environments across network, web, cloud and Active Directory surfaces; deploying them as infrastructure-as-code with Terraform and Ansible; crafting realistic attack chains; and writing rubrics that distinguish real offensive-security judgment from exam-level recall.
Who it is for
The page looks for four or more years of hands-on penetration testing, red-teaming or offensive security, with OSCP strongly preferred (other OSCP-class certifications are also listed), infrastructure-as-code experience, and fluent written English. It says it is currently accepting applicants from Australia, Canada, New Zealand, the United Kingdom and the United States.
Applying on Outlier
What happens after you click
- The link opens this opportunity on Outlier. Create an account there.
- Upload a résumé and a valid ID, then complete any skill screening the project asks for.
- If accepted, the page describes freelance contract work, remote, with no minimum hours stated. Pay is weekly, and rates can vary by project.
Ad If you apply through this link, are hired and complete the platform’s qualifying work, the platform may pay this site a referral fee. That fee does not change your pay or your chances of being hired. Applying on the platform directly is fine.
TrainAI UK is independently operated. We are not affiliated with, endorsed by, or acting for Outlier in any way, and we do not recruit on its behalf.
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We read and checked this listing on Outlier on 14 November 2026, Europe/London. We summarise for readability and do not copy the posting in full. View on Outlier.