Senior AI Security Enterprise Account Executive

Madrona Venture Labs; San Francisco (CA); Hybrid; USD 157,000 - 192,000; Full time

Benefits offered by this job

401k matching

28 days annual leave

Health, dental, and vision coverage

Catered lunches (Pittsburgh office)

Flexible work arrangements

Job summary

Gray Swan AI is seeking an Account Executive to own enterprise sales cycles end-to-end for a technically advanced AI safety and security platform. This is not a replacement-level role; you must credibly engage with technical buyers and drive paid pilots to production deployments.

You will collaborate with founders, engineering, and product to translate inbound interest into six-figure deals and production deployments, while building pipelines and navigating complex, high-stakes sales in a

Qualifications

• Proven enterprise software or platform sales experience.
• Ability to learn complex AI/security concepts.
• Experience selling to AI, security, or financial services sectors.
• Independent pipeline generation and end-to-end ownership.

Responsibilities

• Own the full sales cycle from first contact to close.
• Sell AI safety and security platform including testing and defense solutions.
• Build credibility with technical and executive stakeholders.
• Collaborate with founders, engineering, and product to shape pilots and deployments.
• Generate pipeline through inbound, conferences, referrals, and outbound efforts.
• Maintain momentum through long, multi-stakeholder sales processes.

Skills

Enterprise sales

Technical selling

Buyer engagement

Hunter mentality

Startup mindset

Job description

Gray Swan AI is seeking an Account Executive to own enterprise sales cycles end-to-end for a technically advanced AI safety and security platform. This is not a replacement-level role; you must credibly engage with technical buyers and drive paid pilots to production deployments.

You will collaborate with founders, engineering, and product to translate inbound interest into six-figure deals and production deployments, while building pipelines and navigating complex, high-stakes sales in a