Application Guide

How to Apply for AI Red Teamer

at Trajectory Labs

🏢 About Trajectory Labs

Trajectory Labs is a specialized startup building reinforcement learning environments specifically for frontier AI labs, focusing on training models to be robust, secure, and reliable. What makes them unique is their targeted approach to AI safety infrastructure, working directly with labs developing the most advanced models. Someone might want to work there to be at the cutting edge of AI security research with direct impact on how frontier models are deployed.

About This Role

As an AI Red Teamer at Trajectory Labs, you'll be systematically testing security vulnerabilities in frontier AI models like GPT-5, Claude, and Gemini before they're deployed. This role involves developing Python scripts to automate jailbreak attempts and identify failure modes in advanced AI systems. Your work directly contributes to making AI systems safer and more reliable for real-world deployment.

💡 A Day in the Life

A typical day involves designing and running jailbreak attempts on frontier AI models, analyzing the results to identify security patterns, and developing Python scripts to automate testing procedures. You'll document vulnerabilities and failure modes, then iterate on testing approaches based on your findings, all while working independently with occasional check-ins on progress.

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Interview Prep

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🎯 Who Trajectory Labs Is Looking For

  • Has hands-on experience with adversarial testing of large language models, not just theoretical knowledge of AI security
  • Can demonstrate Python proficiency through actual scripts they've written for testing or security assessment purposes
  • Shows evidence of working independently on complex technical problems with minimal supervision
  • Has a systematic approach to documenting AI failure modes and security vulnerabilities

📝 Tips for Applying to Trajectory Labs

1

Include specific examples of AI model testing you've done - mention particular models you've worked with and what vulnerabilities you identified

2

Showcase Python scripts you've developed for testing or security purposes in your portfolio or GitHub (include links)

3

Demonstrate your understanding of frontier AI models by mentioning specific jailbreak techniques or vulnerabilities you're familiar with

4

Highlight any experience with RL environments or AI safety testing frameworks

5

Emphasize your ability to work independently by describing projects you initiated and completed without close supervision

✉️ What to Emphasize in Your Cover Letter

["Your direct experience with testing advanced AI models and specific vulnerabilities you've identified", "Examples of Python scripts you've developed for security testing or automation", 'How you approach systematic testing and documentation of AI failure modes', "Why you're specifically interested in working on frontier AI models at Trajectory Labs rather than general AI security"]

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Explore Trajectory Labs' website and understand their specific RL environment products
  • → Research the frontier AI labs they likely work with (like Anthropic, OpenAI, Google DeepMind)
  • → Look into current jailbreak techniques and vulnerabilities in models like GPT-4, Claude, and Gemini
  • → Understand the difference between traditional cybersecurity red teaming and AI-specific red teaming
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Walk me through a specific jailbreak or vulnerability you discovered in an advanced AI model
2 Show me a Python script you've written for testing AI security and explain your approach
3 How would you systematically test GPT-5 for security vulnerabilities given limited access?
4 Describe a time you worked independently on a complex technical problem with minimal guidance
5 What do you know about Trajectory Labs' RL environments and how they relate to AI security testing?
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⚠️ Common Mistakes to Avoid

  • Only having theoretical knowledge of AI security without hands-on testing experience
  • Focusing on general cybersecurity skills without specific AI model testing examples
  • Not being able to demonstrate independent work or initiative in past projects

📅 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 Trajectory Labs!

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