How to apply for Senior Forward Deployed Engineer – Enterprise

About Gray Swan

Gray Swan builds tools that automatically assess the risk of AI models. They evaluate AI models for frontier labs and build real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI. The company is about 50 people, well-funded, and growing quickly.

About the role

This is a forward deployed engineering role. You design, build, and deploy enterprise-grade software inside customer environments, integrating Gray Swan's AI security platform into complex production systems. You work at the intersection of software engineering, systems integration, and customer delivery, owning outcomes end-to-end with customers, sales, product, and core engineering.

A typical day

A typical day could involve meeting with a customer's engineering and security teams to map their system architecture, then writing and testing integration code inside their environment. You might also coordinate with Gray Swan's product and core engineering teams on what the customer needs and how to deliver it. The role is customer-facing and delivery-focused, so expect context switching between customer calls and hands-on implementation.

Who Gray Swan is looking for

• Has experience integrating software into customer production systems, not just building internal features.
• Can translate ambiguous, high-stakes requirements into reliable, scalable deployments.
• Is comfortable working directly with customer engineering, security, and platform teams to understand system architectures and constraints.
• Does not want to work on the same narrow surface area every day and can operate in fast-moving, customer-facing environments where reliability, security, and trust matter.

Tips for this application

• Show concrete examples of integrations you built inside customer environments, including the constraints you worked around.
• Name the specific systems you have integrated with (e.g., cloud platforms, identity providers, data pipelines, security tooling) and how you handled reliability and security.
• Explain how you have handled ambiguous requirements from customers and turned them into deployed software.
• Reference Gray Swan's actual work: evaluating AI models for frontier labs and building real-time threat detection and adaptive adversarial red teaming agents.
• Keep the application focused on delivery and integration outcomes, not just coding volume.

What to cover in your cover letter

['Your experience deploying software directly into customer production environments and the outcomes you owned.', 'How you handle ambiguous, high-stakes requirements and translate them into reliable, scalable systems.', 'Your ability to work across customer teams and internal teams (sales, product, core engineering) to deliver.', "Why AI security and Gray Swan's specific work (model risk assessment, threat detection, adversarial red teaming) interests you."]

Research before applying

• Read Gray Swan's website and any public material on how they evaluate AI models and build red teaming agents.
• Look up the backgrounds of the team and any public writing from the company on AI security.
• Understand what 'forward deployed engineer' means in practice at enterprise software companies and how it differs from a core engineering role.
• Find out who Gray Swan's customers are (frontier labs, teams deploying AI) and what their production environments likely look like.

Likely interview topics

Based on the job description, expect questions about:

• Walk through a time you integrated a platform into a customer's production system. What constraints did you face and how did you handle them?
• How do you approach an ambiguous customer requirement with high stakes? Give a specific example.
• How would you design an integration between Gray Swan's platform and a customer's existing security and platform tooling?
• What do you know about AI model risk assessment, threat detection, or adversarial red teaming, and how would you explain Gray Swan's value to a customer engineer?
• How do you balance customer-facing delivery work with coordination across sales, product, and core engineering?

Common mistakes to avoid

• Applying with only internal product engineering experience and no examples of customer-facing integration or deployment.
• Describing technical work without mentioning reliability, security, or production constraints.
• Showing no familiarity with AI security, model risk, or Gray Swan's specific products.