Chief AI Cyber Safety Architect

Madrona Venture Labs; United States; On-site; USD 230,000 - 280,000; Full time

Benefits offered by this job

401k with up to 4% matching

28 days annual leave

Health, dental, and vision coverage

Catered lunches (Pittsburgh office)

Flexible work arrangements

Visa sponsorship available for rare/ep

Job summary

Gray Swan is seeking a seasoned cybersecurity leader in the United States to serve as the technical authority on AI-enabled cyber risk. You will design adversarial evaluations of frontier LLMs, translate cybersecurity expertise into scalable benchmarks, and drive safety standards across red-teaming, evaluation, and defenses.

You will mentor a world-class team and collaborate with AI labs and researchers to reduce catastrophic cyber risks from advanced AI systems.

Qualifications

• Deep technical expertise in offensive cybersecurity, vulnerability research, exploit development, penetration testing, malware analysis, reverse engineering, or a closely related field.
• 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.
• Thrive in highly ambiguous, fast-moving environments where you'll define strategy while building entirely new capabilities.
• A builder who enjoys creating teams, infrastructure, and evaluation systems from scratch.

Responsibilities

• 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.
• Partner closely with machine learning engineers to translate cybersecurity expertise into scalable benchmarks, classifiers, guardrails, automated detection systems, and evaluation infrastructure for both internal products and frontier AI lab deployments.
• Develop and maintain Gray Swan’s catastrophic cyber harm taxonomy, continuously evolving cyber evaluation frameworks as frontier model capabilities rapidly advance.
• Produce technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, and internal stakeholders, helping guide responsible model deployment and security mitigations.
• Build, mentor, and lead a world-class team of cybersecurity subject matter experts while establishing scalable evaluation processes, quality standards, and technical infrastructure.
• Represent Gray Swan as the company's cybersecurity authority, collaborating with frontier AI labs, security researchers, government partners, and the broader AI safety and cybersecurity communities.

Skills

Offensive cybersecurity

Vulnerability research

Adversarial AI security

AI red-teaming

LLM security research

ML/AI engineering collaboration

Python

Go

Rust

Tools

Python

Go

Rust

Job description

Gray Swan is seeking a seasoned cybersecurity leader in the United States to serve as the technical authority on AI-enabled cyber risk. You will design adversarial evaluations of frontier LLMs, translate cybersecurity expertise into scalable benchmarks, and drive safety standards across red-teaming, evaluation, and defenses.

You will mentor a world-class team and collaborate with AI labs and researchers to reduce catastrophic cyber risks from advanced AI systems.