Head of Cyber Safety

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Gray Swan

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2023

🤖 Artificial Intelligence

🔒 Cybersecurity

☁️ SaaS

Artificial Intelligence • Cybersecurity • SaaS

Gray Swan is an AI security company that builds a research-backed platform to protect AI deployments across the entire lifecycle, offering input/output filtering, continuous monitoring, automated vulnerability testing, and enterprise-focused red-teaming services. The company combines frontier research, benchmarks, and large-scale red-team competitions to discover emerging attacks and deliver adaptive, integrable protections for AI agents, models, and connected tools. Gray Swan’s products and services are aimed at enterprises, AI labs, and security researchers seeking pre-deployment assessments, post-deployment monitoring, and compliance-ready defenses.

📋 Description

• 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 with machine learning engineers to translate cybersecurity expertise into scalable benchmarks, classifiers, guardrails, automated detection systems, and evaluation infrastructure. • Develop and maintain Gray Swan’s catastrophic cyber harm taxonomy and evolve cyber evaluation frameworks as frontier model capabilities advance. • Produce technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, and internal stakeholders. • Build, mentor, and lead a cybersecurity subject matter expert team 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 AI safety and cybersecurity communities.

🎯 Requirements

• Deep technical expertise in offensive cybersecurity, vulnerability research, exploit development, penetration testing, malware analysis, reverse engineering, or a 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 operate in highly ambiguous, fast-moving environments while defining strategy and building new capabilities. • Experience developing machine learning models, AI security classifiers, or automated cyber detection systems is a bonus. • Experience red-teaming frontier language models, jailbreaking, prompt injection research, or agentic AI evaluations is a bonus. • Experience with frontier AI labs, national security organizations, or leading cybersecurity research teams is a bonus. • Background in threat intelligence, autonomous cyber operations, AI agent security, or AI governance is a bonus. • Strong software engineering experience in Python, Go, Rust, or other systems programming languages is a bonus. • Must be legally authorized to work in the United States.

🏖️ Benefits

• Performance based bonus • Meaningful equity package • 401k with up to 4% matching • 28 days annual leave (vacation + holidays) • Health, dental, and vision coverage • Catered lunches (Pittsburgh office) • Flexible work arrangements • Visa sponsorship available for exceptional candidates