Red Team Lead for Offensive Cybersecurity AI Training

Lead the design and validation of offensive security evaluation frameworks, taxonomies, and benchmarks that train and evaluate next generation AI systems using real world red team expertise. This contractor role is remote and focuses on translating hands on offensive cybersecurity knowledge into rigorous, well documented evaluation tasks and scoring rubrics while maintaining strict ethical boundaries.

• Develop comprehensive taxonomies for cyber capability tasks and attack stages relevant to modern threat landscapes.
• Design and validate evaluation frameworks for offensive security, emphasizing real world scenarios involving exploit chains, malware, cloud and application security, and social engineering.
• Create safe and effective proxy tasks that simulate advanced attack vectors while enforcing ethical and operational boundaries.
• Formulate robust scoring rubrics to assess attack sophistication, coverage, and impact across diverse domains.
• Review, critique, and improve benchmarks for red team operations to ensure alignment with evolving security risks and industry best practices.
• Produce clear, well documented methodologies and technical write ups that communicate complex security concepts to technical and non technical audiences.
• Collaborate asynchronously with project stakeholders to iterate on frameworks and incorporate feedback into deliverables.
• Apply your domain expertise to help train next generation AI systems, no prior AI experience required.

• Required skills: cyber security, exploit chains, cloud and application security, malware, social engineering, and maintaining ethical boundaries in offensive assessments.
• Minimum 5 years of hands on experience in offensive cybersecurity, red teaming, exploit development, or vulnerability research, with 8 to 20 years preferred for senior contributors.
• Proven track record in roles such as principal security engineer, exploit developer, cloud red team lead, malware reverse engineer, or security researcher focused on attack chains or social engineering.
• Deep technical expertise in cyber attack methodologies, exploit chains, and cloud or application security assessments.
• Strong background in malware analysis, reverse engineering, or social engineering tactics and defenses is highly valued.
• Demonstrated ability to produce clear, actionable written and verbal communication for varied audiences.
• Advanced degree, professional security certifications, or equivalent operational experience are highly valued.
• Experience building benchmarking or evaluation frameworks in cybersecurity is a plus.

• Engagement type: Contractor.
• Location: Remote.
• Role contributes to a customer s critical cybersecurity project and to training AI systems with domain expert input.

• Pay rate: $50.00 to $90.00 per hour.

• Must be able to engage as an independent contractor under the applicable laws and agreements for this remote role.
• No prior experience in AI is required; domain expertise in offensive cybersecurity is the primary qualification.

Interested?