Note: The job is a remote job and is open to candidates in USA. Handshake is a career and AI data company that supports job seekers, employers, educational institutions, and frontier AI labs. The Cybersecurity Red Teamer will evaluate whether AI models can generate functional malware, exploit code, attack tooling, or operational cyberattack guidance by designing adversarial tests, assessing model outputs, and documenting real-world exploitability. The role also contributes to cybersecurity evaluation frameworks and collaborates with red teamers, AI researchers, and policy teams to improve model safety.
Responsibilities
- Design technically grounded adversarial prompts that test whether models provide meaningful assistance across the cyber kill chain, from reconnaissance through exfiltration and impact
- Evaluate model-generated code and technical output for functional correctness, determining whether outputs represent real exploits, plausible attack tooling, or nonfunctional noise
- Test model behavior across offensive categories, including malware generation, vulnerability exploitation, social engineering, credential harvesting, privilege escalation, command-and-control infrastructure, and data exfiltration
- Probe dual-use boundaries by testing how models respond to queries that combine legitimate security research, penetration testing, and defensive operations with offensive applications
- Simulate attacker personas at varying skill levels, including opportunistic, intermediate, and advanced or APT-level actors
- Test multi-step and multi-turn attack chains, including scenarios in which early turns establish benign context before pivoting to malicious requests
- Score model responses using structured harm taxonomies and severity rubrics calibrated to real-world exploitability
- Document findings with clear technical reasoning, including what a response gets right, what it gets wrong, and what level of attacker it could realistically assist
- Contribute to the development and refinement of cybersecurity-specific evaluation frameworks and threat models
- Collaborate with red teamers, AI researchers, and policy teams to translate findings into actionable model improvements
- Stay current on evolving tactics, techniques, and procedures, CVEs, jailbreak techniques, and the intersection of AI and offensive security
Skills
- • Professional experience in offensive security, penetration testing, red teaming, vulnerability research, malware analysis, threat intelligence, or incident response
- • Ability to read, write, and evaluate code in languages commonly used for offensive tooling, such as Python, PowerShell, Bash, C/C++, or JavaScript
- • Understanding of common attack frameworks, techniques, and procedures, including MITRE ATT&CK and OWASP
- • Ability to assess the functional correctness and real-world exploitability of model-generated technical output
- • Strong hands-on experience using multiple LLMs, such as ChatGPT, Claude, Gemini, or open-source models
- • Creative and adversarial problem-solving skills
- • Clear and precise written communication, including the ability to explain technical risk to nonspecialist audiences
- • Strong ethical judgment and the ability to separate adversarial thinking from personal values
- • Ability to work independently while collaborating effectively in a feedback-heavy, distributed environment
- • You have spent years breaking into systems and want to apply that mindset to testing AI models
- • You can examine a model-generated reverse shell, phishing template, or privilege-escalation script and quickly determine whether it would work in a real environment
- • You think in kill chains and attack graphs, not just individual prompts
- • You understand that the difference between a useful coding assistant and a dangerous one often comes down to context, specificity, and operational detail
- • You closely follow the offensive-security community and stay current when new techniques emerge
- • You care about AI safety because you understand what can happen when powerful tools are used irresponsibly
- • You can collaborate effectively with a team whether you are working from Seattle or remotely
- Candidates must be able to engage with this material professionally, responsibly, and sustainably
- • Relevant certifications, such as OSCP, OSCE, GPEN, GXPN, CRTO, CRTL, CEH, or similar
- • Active or previous security clearance
- • Experience with exploit development, reverse engineering, or binary analysis
- • Background in cloud security, container security, or infrastructure-as-code attack surfaces
- • Familiarity with AI and machine-learning attack surfaces, including prompt injection, model extraction, training-data poisoning, and adversarial examples
- • Experience building or operating command-and-control frameworks, custom implants, or offensive tooling
- • A bug-bounty track record or published CVEs
- • Previous work in trust and safety, content moderation, or AI evaluation
- • Familiarity with LLM APIs or evaluation tooling
Benefits
- Work from Seattle or remotely from anywhere within the United States
- Flexible work arrangement, including part-time availability
Company Overview