Application Guide

How to Apply for Head of Cyber Safety

at Gray Swan

🏢 About Gray Swan

Gray Swan is a cutting-edge AI security company focused on automatically assessing the risks of AI models, particularly frontier LLMs. Working here means being at the forefront of AI safety, collaborating with top talent to ensure AI systems are secure and trustworthy. The remote-first culture and mission-driven environment make it an exciting place for those passionate about AI security.

About This Role

As Head of Cyber Safety, you'll lead the cyber safety capability, acting as the technical authority on AI-enabled cyber risk. You'll design adversarial evaluations of frontier LLMs, translate cybersecurity expertise into scalable benchmarks, and produce risk assessments for top AI labs and enterprises. This role is impactful because your work will directly shape how AI models are secured against offensive cyber capabilities, influencing industry standards.

💡 A Day in the Life

A typical day might involve reviewing latest AI model capabilities, designing new evaluation scenarios for offensive cyber risks, and collaborating with engineers to implement guardrails. You'd also meet with clients to present risk assessments and discuss how to mitigate emerging threats, while mentoring your team on technical challenges.

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🎯 Who Gray Swan Is Looking For

  • Deep expertise in cybersecurity, with a focus on offensive techniques like vulnerability discovery and exploit development.
  • Experience in AI/ML, particularly with LLMs, and understanding of their security implications.
  • Proven ability to design and implement scalable security evaluations, benchmarks, or automated detection systems.
  • Strong leadership skills to guide the cyber safety team and influence external stakeholders.
  • Excellent communication to translate complex technical findings into actionable recommendations for varied audiences.

📝 Tips for Applying to Gray Swan

1

Highlight specific projects where you've applied offensive security techniques to AI systems, such as red-teaming LLMs or developing exploits.

2

Showcase your experience with building scalable security tools or benchmarks, emphasizing measurable impact.

3

Demonstrate thought leadership by sharing relevant publications, talks, or open-source contributions in AI security.

4

Tailor your resume to emphasize both cybersecurity and AI expertise, using keywords from the job description.

5

In your cover letter, propose a concrete idea for an adversarial evaluation you'd like to implement at Gray Swan, showing proactive thinking.

✉️ What to Emphasize in Your Cover Letter

["Your unique blend of cybersecurity and AI expertise, and how it aligns with Gray Swan's mission.", 'Specific examples of past work in assessing AI cyber risks or developing security frameworks.', "Your vision for advancing cyber safety evaluations for frontier models, and how you'd contribute from day one.", 'Your leadership experience and ability to drive a team toward impactful outcomes.']

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Explore Gray Swan's website and blog to understand their products and recent research areas.
  • → Read recent publications or talks from the team to grasp their methodology and current challenges.
  • → Look into the broader AI security landscape, including other companies and academic work, to position your application.
  • → Investigate any recent incidents or debates about AI cyber capabilities to inform your interview talking points.
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 How would you design an adversarial evaluation to test an LLM's ability to discover vulnerabilities in code?
2 Describe a time you had to balance thoroughness with scalability when creating security benchmarks.
3 How do you stay updated on the latest offensive cyber capabilities and apply that to AI risk assessment?
4 What is your approach to developing a cyber harm taxonomy, and how would you keep it current as models evolve?
5 How would you communicate a complex cyber risk assessment to a non-technical executive or client?
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⚠️ Common Mistakes to Avoid

  • Underestimating the importance of AI/ML knowledge; even if you're a cybersecurity expert, you must show fluency in AI concepts.
  • Focusing solely on defensive security; this role is about adversarial evaluations, so highlight offensive skills.
  • Being too theoretical without practical examples; ensure you mention concrete tools, frameworks, or projects you've built.

📅 Application Timeline

This position is open until filled. However, we recommend applying as soon as possible as roles at mission-driven organizations tend to fill quickly.

Typical hiring timeline:

1

Application Review

1-2 weeks

2

Initial Screening

Phone call or written assessment

3

Interviews

1-2 rounds, usually virtual

✓

Offer

Congratulations!

Ready to Apply?

Good luck with your application to Gray Swan!

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