Job Title
Red Team Lead (Offensive Cybersecurity) – AI Trainer
Job Type
Contractor
Compensation Structure
Hourly contract position. Compensation is paid based on hours worked and approved project time.
Location
Remote
Job Summary
We are looking for experienced Red Team Leads and Offensive Cybersecurity Experts to support AI training and evaluation by contributing real-world expertise in offensive security, adversarial testing, and cybersecurity assessment. In this role, you will help improve next-generation AI systems by applying your knowledge of attack methodologies, exploit development, cloud security, application security, malware analysis, and security evaluation frameworks.
This is an hourly-paid contract opportunity, not a traditional penetration testing or security operations role. Contributors will complete project-based AI training and evaluation tasks that help AI models better understand cybersecurity concepts, offensive security methodologies, risk assessment, and responsible security reasoning.
No prior AI experience is required. What matters most is your cybersecurity expertise, technical judgment, and ability to communicate complex security concepts clearly.
Key Responsibilities
- Contribute to AI training, benchmarking, and evaluation projects involving offensive cybersecurity and red team scenarios.
- Develop taxonomies covering modern cyber capabilities, attack stages, adversary techniques, and offensive security workflows.
- Design and validate evaluation frameworks based on realistic offensive security scenarios involving exploit chains, cloud security, application security, malware, and social engineering.
- Develop safe proxy evaluation tasks that simulate real-world attack scenarios while maintaining appropriate ethical and security boundaries.
- Create scoring rubrics to assess attack sophistication, coverage, effectiveness, and defensive resilience.
- Review AI-generated security analyses, benchmarks, and technical content for accuracy, consistency, and real-world applicability.
- Produce clear technical documentation, methodologies, and written evaluations for both technical and non-technical audiences.
- Collaborate with multidisciplinary teams to continuously improve cybersecurity evaluation frameworks and AI model performance.
Required Skills and Qualifications
- 5+ years of professional experience in offensive cybersecurity, red teaming, exploit development, vulnerability research, or a closely related field.
- Deep understanding of offensive security methodologies, exploit chains, application security, cloud security, and adversarial techniques.
- Experience with malware analysis, reverse engineering, vulnerability assessment, penetration testing, or social engineering methodologies.
- Strong analytical and technical problem-solving skills with exceptional attention to detail.
- Excellent written and verbal communication skills with the ability to explain complex cybersecurity concepts clearly.
- Ability to work independently in a remote, collaborative environment.
Preferred Qualifications
- 8–20 years of experience in offensive security, red teaming, security research, or cybersecurity leadership roles.
- Experience as a Principal Security Engineer, Red Team Lead, Exploit Developer, Security Researcher, Malware Reverse Engineer, or Cloud Security Specialist.
- Advanced degree, industry-recognized cybersecurity certifications, or equivalent operational experience.
- Experience developing cybersecurity benchmarks, evaluation frameworks, or security assessment methodologies.
- Interest in applying offensive security expertise to AI training, evaluation, and emerging cybersecurity technologies.
Additional Information
This opportunity is ideal for experienced offensive cybersecurity professionals who want to apply their expertise to the development of responsible AI systems. Your contributions will directly improve how next-generation AI models reason about offensive security, adversarial techniques, vulnerability assessment, cloud security, malware analysis, and cybersecurity best practices while helping establish robust security evaluation standards.
Job Type: Contract
Pay: $50.00 - $90.00 per hour
Benefits:
Work Location: Remote
