Senior Account Executive – AI Security

Gray Swan; Boston (MA); On-site; USD 157,000 - 192,000; Full time

Benefits offered by this job

401k with up to 4% matching

28 days annual leave

Health, dental, and vision coverage

Catered lunches

Flexible work arrangements

Job summary

Gray Swan is seeking an Account Executive to own enterprise sales cycles for a cutting-edge AI safety platform. In this role, you will work closely with founders and technical teams to convert inbound interest into paid pilots and secure long-term deployments.

You should have proven experience in enterprise software sales, with the ability to engage technical buyers effectively. Our competitive compensation package includes a base salary of $157k-$192k and meaningful equity opportunities.

Qualifications

• Proven experience selling enterprise software or platforms, ideally in AI or security.
• Experience selling into or strong relationships within financial services, healthcare, or insurance organizations.
• Ability to thrive in early-stage startup environments.

Responsibilities

• Own the full sales cycle from first conversation through close.
• Sell a complete AI safety and security platform.
• Build credibility with technical and executive stakeholders.
• Generate pipeline through a mix of inbound leads, conference networking, referrals, and outbound efforts.
• Work directly with founders to shape customer pilots.

Skills

Proven experience selling enterprise software

Comfort learning technical material

Experience selling into AI or security

Ability to operate independently

Highly motivated and disciplined

Job description

Overview

Gray Swan protects organizations from emerging AI security threats. We build real-time threat detection, automated validation, and adaptive defenses for AI labs and enterprises. We’re a team of ~25 people, well-funded, and growing fast. We have strong traction and globally recognized customers, which means employees here take on real responsibility and meaningful equity from day one. This is a high-ownership environment where you’ll work on hard problems, move quickly, and help shape both the product and the company. Many people join Gray Swan because our mission matters. We’re doing practical, high-impact work in AI safety, that sense of purpose is a core reason why engineers and researchers choose us.

About 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.
• Partner with our SDR to convert inbound interest into qualified opportunities while continuing to source and develop your own leads.
• 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.

Note: 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

Compensation Range: $157K - $192K