Senior Account Executive - AI Security

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

About Gray Swan

Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.

We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..

Learn more about how we work.

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.

If you’re energized by building something early, working hard, and closing meaningful six-figure deals in a new and rapidly evolving market, this role is likely a great fit.

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 If You Have:

• 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 don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.

You’ll Thrive Here If You:

• 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