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Salary: USD 230,000 - 280,000 / annual
Gray Swan is building AI safety and security infrastructure for frontier AI labs. The company evaluates AI models for offensive cyber capabilities and develops real-time threat detection and adversarial red-teaming agents. With ~50 employees and strong funding, Gray Swan directly influences how the world deploys AI systems at scale.
As Head of Cyber Safety, you will build and lead Gray Swan's cyber safety capability from the ground up, serving as the technical authority on AI-enabled cyber risk. You'll design and lead adversarial evaluations of frontier LLMs for offensive cyber capabilities, including vulnerability discovery, exploit development, malware generation, privilege escalation, social engineering, persistence, and autonomous cyber operations across text, agentic, and multimodal systems.
Key responsibilities include:
- Design and lead adversarial evaluations of frontier LLMs for offensive cyber capabilities
- Partner with machine learning engineers to translate cybersecurity expertise into scalable benchmarks, classifiers, guardrails, and automated detection systems
- Develop and maintain Gray Swan's catastrophic cyber harm taxonomy and evolve cyber evaluation frameworks
- Produce technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, and internal stakeholders
- Build, mentor, and lead a world-class team of cybersecurity subject matter experts
- Represent Gray Swan as the company's cybersecurity authority, collaborating with frontier AI labs, security researchers, government partners, and the broader AI safety community
This role sits at the intersection of offensive security, AI safety, and machine learning. You'll transform deep cybersecurity expertise into scalable evaluation methodologies and safety infrastructure that help establish industry standards for frontier model security.
REQUIREMENTS:
- Deep technical expertise in offensive cybersecurity, vulnerability research, exploit development, penetration testing, malware analysis, reverse engineering, or closely related field through industry, research, or equivalent experience
- Significant experience assessing advanced cyber threats, offensive tooling, or AI-enabled cyber capabilities, especially in critical infrastructure domains
- Hands-on experience conducting adversarial evaluations, AI red-teaming, LLM security research, or building evaluation datasets for frontier AI systems
- Comfortable operating at the intersection of cybersecurity research, AI safety, and machine learning engineering
- Ability to thrive in highly ambiguous, fast-moving environments where you'll define strategy while building entirely new capabilities
- Demonstrated ability to build teams, infrastructure, and evaluation systems from scratch
BONUS QUALIFICATIONS:
- Experience developing machine learning models, AI security classifiers, or automated cyber detection systems
- Hands-on experience red-teaming frontier language models, jailbreaking, prompt injection research, or agentic AI evaluations
- Experience working with frontier AI labs, national security organizations, or leading cybersecurity research teams
- Background in threat intelligence, autonomous cyber operations, AI agent security, or AI governance
- Strong software engineering experience in Python, Go, Rust, or other systems programming languages
