Application Guide

How to Apply for Product Designer, Arena, Remote

at Gray Swan

🏢 About Gray Swan

Gray Swan is an AI security company at the forefront of making AI systems safe and trustworthy. Working here means tackling one of the most critical challenges in AI—risk assessment and mitigation—with a small, focused team. The remote culture and mission-driven work offer a unique blend of autonomy and impact.

About This Role

As the Product Designer for Arena, you will design the core UI that security researchers and engineers use to test and secure AI models. Your work directly enables users to navigate complex workflows intuitively, making AI safety more accessible. This role is high-impact because it shapes how professionals interact with cutting-edge AI evaluation tools.

💡 A Day in the Life

Your day might start with a stand-up with product and engineering to align on priorities. You'll spend time sketching new flows for Arena's testing interface, then refine high-fidelity mockups in Figma. Afternoons involve reviewing design system components with engineers and conducting user research sessions with security professionals to validate your designs.

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Interview Prep

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🎯 Who Gray Swan Is Looking For

  • A designer with 3+ years of experience in product design, demonstrated through a portfolio of end-to-end projects (from concept to launch).
  • Strong visual design skills with the ability to create clean, intuitive interfaces for technical users (e.g., developers, security researchers).
  • Proven experience building and maintaining design systems, including reusable components, patterns, and visual standards.
  • Excellent collaboration skills, comfortable working cross-functionally with product managers, engineers, and researchers in a fast-paced startup environment.

📝 Tips for Applying to Gray Swan

1

Tailor your portfolio to highlight projects involving complex workflows or data-heavy interfaces—ideally for technical audiences.

2

In your resume, explicitly mention any experience with design systems, including the tools used (e.g., Figma, Storybook) and scale of the system.

3

Research Gray Swan's Arena product and mention specific UI challenges you see (e.g., balancing simplicity with advanced controls) in your cover letter.

4

Showcase your ability to iterate quickly by including case studies with multiple design iterations and user testing feedback.

5

If you have experience in AI or security domains, highlight it—even if it's from side projects or academic work.

✉️ What to Emphasize in Your Cover Letter

['Emphasize your passion for AI safety and how your design skills can help make complex security tools more accessible.', 'Highlight your end-to-end design process and examples of owning a product from sketches to production.', 'Show your experience in building design systems and maintaining consistency across a product.', 'Mention your comfort working with technical teams and translating their needs into intuitive interfaces.']

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Read Gray Swan's website and blog to understand their mission and current product offerings (e.g., Arena, Red Team).
  • → Explore their GitHub or any public technical documentation to grasp the product's complexity and user base.
  • → Look at competitors in AI security (e.g., Anthropic's evaluation tools, other red-teaming platforms) to understand the landscape.
  • → Check out any talks or articles by Gray Swan's founders or team members on AI safety and design challenges.
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Walk me through your design process for a complex workflow—how did you simplify it for users?
2 How would you approach designing a dashboard for AI model risk assessment? What metrics would you prioritize?
3 Give an example of how you've built or contributed to a design system. What were the challenges?
4 How do you collaborate with engineers to ensure your designs are implemented accurately?
5 Tell us about a time you had to balance user needs with technical constraints. How did you handle it?
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⚠️ Common Mistakes to Avoid

  • Submitting a generic portfolio without case studies relevant to technical or security domains.
  • Ignoring the company's mission—failing to mention AI safety or the product's purpose in your application.
  • Over-emphasizing visual design without demonstrating deep understanding of user flows and interaction design for complex systems.

📅 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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