Application Guide

How to Apply for Head of AI Red Teaming

at Trajectory Labs, PBC

🏢 About Trajectory Labs, PBC

Trajectory Labs is a public benefit corporation building RL environments for frontier AI labs to train robust, secure, and reliable models. As a small startup, you'd work directly on the cutting edge of AI safety, with your red-teaming work directly shaping how the most advanced models are trained and deployed. The remote-first culture and focus on automating safety evaluations mean you'll have high autonomy and visible impact from day one.

About This Role

As Head of AI Red Teaming, you'll lead a team responsible for finding and exploiting vulnerabilities in frontier AI models, with a particular focus on prompt injection. You'll also own the automation of red-teaming workflows using coding agents, aiming for 10x efficiency gains, and work directly with frontier lab customers to scope needs, deliver results, and shape pricing and product strategy. This is a hands-on leadership role where you'll balance people management, technical innovation, and customer-facing work.

💡 A Day in the Life

You might start your day with a stand-up with your red team, reviewing progress on ongoing evaluations and prioritizing new attack vectors. Later, you'll dive into code to prototype an automation script for a repetitive red-teaming task, then meet with a frontier lab customer to scope a new project and discuss pricing. You'll end the day reviewing a report on prompt injection vulnerabilities and planning how to scale your team's impact.

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🎯 Who Trajectory Labs, PBC Is Looking For

  • Proven experience managing and growing technical teams, ideally in red-teaming, security, or AI safety, with a track record of setting quality standards and scaling operations.
  • Strong technical fluency in code and LLMs, including hands-on experience with prompt injection attacks, evaluation methodologies, and using coding agents to automate workflows.
  • Background in cybersecurity, software engineering, or AI safety research, with a deep understanding of adversarial techniques against AI systems.
  • Entrepreneurial ownership mindset, comfortable scoping customer needs, making pricing decisions, and driving product strategy in a fast-paced startup environment.

📝 Tips for Applying to Trajectory Labs, PBC

1

Highlight any experience you have with prompt injection specifically—this is a core focus of the role—and quantify your impact (e.g., number of vulnerabilities found, efficiency improvements).

2

Demonstrate your ability to automate workflows using coding agents; provide concrete examples of how you've used tools like GPT-4, Claude, or custom agents to scale red-teaming or security testing.

3

Emphasize your experience working with frontier AI labs or similar high-stakes customers, and show you understand their unique needs and constraints.

4

Show evidence of building and managing red teams, including how you've expanded teams, set quality standards, and mentored team members.

5

Tailor your application to Trajectory Labs' mission as a PBC—express genuine interest in AI safety and reliability, and connect your work to their goal of training robust models.

✉️ What to Emphasize in Your Cover Letter

['Your specific experience leading red-teaming operations for large language models, including managing teams and developing evaluation methodologies.', 'Concrete examples of automating manual red-teaming tasks using coding agents, with metrics showing efficiency gains (e.g., 10x speedup).', 'Your ability to interface with customers, scope their needs, and translate them into product and pricing strategies.', "Your passion for AI safety and alignment with Trajectory Labs' mission as a public benefit corporation."]

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Explore Trajectory Labs' website and any public materials to understand their specific approach to building RL environments and their current customers or partners.
  • → Research recent advancements in prompt injection attacks and defenses, as well as common red-teaming methodologies for LLMs (e.g., OWASP Top 10 for LLMs).
  • → Look into the founders and team backgrounds to understand their technical expertise and vision for the company.
  • → Familiarize yourself with the competitive landscape of AI red-teaming and safety evaluation startups, and how Trajectory Labs differentiates itself.
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 How would you design and scale a red-teaming program for a new frontier model, from team structure to evaluation metrics?
2 Describe a time you automated a manual security or red-teaming workflow using coding agents. What tools did you use and what was the impact?
3 How do you prioritize which vulnerabilities or attack vectors to focus on when red-teaming an LLM, especially for prompt injection?
4 Tell us about your experience managing a red team: how do you hire, train, and retain top talent while maintaining quality standards?
5 How would you approach pricing and product strategy for red-teaming services sold to frontier AI labs?
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⚠️ Common Mistakes to Avoid

  • Focusing only on traditional cybersecurity without connecting it to AI/LLM-specific threats like prompt injection—this role requires AI fluency.
  • Downplaying the importance of automation; candidates who don't show enthusiasm for using coding agents to scale workflows may seem out of touch with the role's core challenge.
  • Neglecting to demonstrate customer-facing or product strategy experience; this is not just a technical role, it requires business acumen and ownership.

📅 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, PBC!

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