Senior Account Executive – AI Security

The Role

As an Account Executive at Gray Swan AI, you’ll own enterprise sales cycles end-to-end for a highly technical AI safety and security platform. This is not a replacement-level software sales role. We’re looking for someone who can operate credibly with technical buyers, learn complex products quickly, and thrive in a fast-moving startup environment where ownership and initiative matter.

You’ll work closely with founders, engineering, and product to turn inbound interest into paid pilots and long-term production deployments. This role blends enterprise selling, technical curiosity, and startup hustle, with significant autonomy and upside.

What You’ll Do

• Own the full sales cycle from first conversation through close, often starting with paid pilots and expanding to production deployments.
• Sell a complete AI safety and security platform, including automated adversarial testing/red teaming and runtime defensive solutions for AI systems.
• Build credibility with technical and executive stakeholders across AI, security, and engineering teams.
• Learn and communicate technical concepts clearly, working closely with internal technical teams to scope solutions and answer customer questions.
• Engage buyers in regulated and high-stakes industries such as financial services, healthcare, and insurance.
• Generate pipeline through a mix of inbound leads, conference networking, referrals, and outbound efforts.
• Maintain strong momentum through long, multi-stakeholder sales processes.
• Work directly with founders, product, and engineering to shape customer pilots and deployments.
• Provide feedback from the field to influence product direction, positioning, and go-to-market strategy.

What You Bring

• Proven experience selling enterprise software or platforms, ideally in AI, security, or adjacent technical domains.
• Comfort learning technical material and engaging with technical buyers, even if you are not an engineer by training.
• Experience selling into or having strong relationships within AI, security, financial services, healthcare, or insurance organizations.
• Ability to operate independently, generate pipeline, and own outcomes end-to-end.
• Ability to thrive in early-stage startup environments, comfortable wearing multiple hats, and contributing beyond a narrowly defined sales role.
• Highly motivated, disciplined, and willing to work hard to build something meaningful.
• Presence, credibility, and sound judgment to customer interactions.

Bonus Points

• Prior experience selling highly technical or emerging technology products.
• Existing relationships with AI labs, security teams, or enterprise engineering organizations.
• Experience closing six-figure enterprise deals with long, consultative sales cycles.
• Familiarity with AI safety, security, testing, or infrastructure-level software.

If You Thrive Here

• Want to help define how enterprise AI safety and security software is sold.
• Enjoy learning complex products and explaining them clearly to customers.
• Are motivated by ownership, accountability, and upside rather than rigid structure.
• Are excited by Gray Swan’s mission to help organizations deploy AI safely and securely.

What we offer

• A competitive compensation package designed to reward impact and incentivize growth.
• Our compensation philosophy is informed by our current valuation and recent industry data. Base salary is targeted to $157k-$192k + commission ($314-$384k OTE)
• Meaningful equity participation
• Work from our office in Pittsburgh, or remotely
• Opportunity for outsized earnings driven by high inbound interest and large deal sizes
• Benefits:
• 401k with up to 4% matching
• 28 days annual leave (vacation + holidays)
• Health, dental, and vision coverage
• Catered lunches (Pittsburgh office)
• Flexible work arrangements