How to apply for Senior Account Executive – AI Security

About Gray Swan

Gray Swan is an AI security company that builds tools to automatically assess risks in AI models. They work with leading frontier labs and help teams deploying AI detect threats and run adversarial red teaming. The company is around 50 people, well-funded, and growing quickly.

About the role

This is a full-cycle enterprise sales role for a highly technical AI safety and security platform. You will work with founders, engineering, and product to turn inbound interest into paid pilots and long-term production deployments. The job description states this is not a replacement-level software sales role.

A typical day

A typical day might include calls with inbound leads, working with engineering or product to answer technical questions, and moving a paid pilot toward a production deployment. You would likely spend time learning about AI security threats and how Gray Swan's tools address them. The job description does not specify daily routines, so ask about team structure and sales process in interviews.

Who Gray Swan is looking for

• Can operate credibly with technical buyers and learn complex products quickly.
• Has experience owning enterprise sales cycles end-to-end, including paid pilots and expansion to production deployments.
• Is comfortable working closely with founders, engineering, and product in a small startup.
• Can close six-figure deals in a new and rapidly evolving market.

Tips for this application

• Read the Gray Swan website and any linked material about how they work before writing anything. The job description links to 'Learn more about how we work.'
• In your application, give one or two concrete examples of enterprise sales cycles you owned end-to-end, including deal sizes and how you worked with technical buyers.
• Show that you understand the difference between selling AI security tools and selling generic software. Use terms from the job description like adversarial red teaming, threat detection, and AI model evaluation.
• Do not write a generic cover letter. Mention Gray Swan by name and refer to their work with frontier labs or their real-time threat detection products.
• If you have sold to security, AI, or infrastructure teams, state that directly and explain what you had to learn technically to close those deals.

What to cover in your cover letter

['Your experience owning full enterprise sales cycles from first conversation through close, especially starting with paid pilots.', 'How you have worked with technical buyers and learned complex products quickly.', 'Why you want to sell AI security specifically, not just any software.', 'Your ability to operate with autonomy and initiative in a small, fast-moving startup.']

Research before applying

• Read the Gray Swan website, especially any page about how they work and their products for AI model evaluation and threat detection.
• Look up what adversarial red teaming means and why companies deploying AI need it.
• Find out who Gray Swan's customers are, such as frontier labs or teams deploying AI agents.
• Check if Gray Swan has published any blog posts, papers, or talks about AI security.

Likely interview topics

Based on the job description, expect questions about:

• Walk through an enterprise deal you closed end-to-end. What was the deal size, who were the buyers, and how did you start with a pilot?
• How do you learn a technical product well enough to sell it to engineers or security teams?
• What do you know about AI security risks, such as adversarial attacks or model evaluation?
• How would you turn inbound interest into a paid pilot at Gray Swan?
• Describe a time you worked with founders or product teams to close a deal. What was your role?

Common mistakes to avoid

• Writing a cover letter that could be sent to any software company. This role is specifically about AI security and technical buyers.
• Claiming to be technical without giving examples of how you learned a complex product or worked with engineers.
• Focusing only on closing deals and ignoring the pilot-to-production expansion model described in the job description.