Senior Account Executive – AI Security

OpenKrill; United States; On-site; USD 157,000 - 192,000; Full time

Benefits offered by this job

401k matching

Vacation + holidays

Health/dental/vision

Catered lunches

Flexible work arrangements

Equity participation

Job summary

Gray Swan AI is seeking an Account Executive to own enterprise sales cycles end-to-end for a technical AI safety and security platform. You will work with founders, engineering, and product to convert inbound interest into pilots and production deployments.

Ideal candidates will credibly engage with technical buyers, learn complex products quickly, and thrive in a fast-moving startup where ownership and initiative matter. Remuneration includes base salary with commissions and equity.

Qualifications

• Proven experience selling enterprise software or platforms.
• Comfort learning technical material and engaging with technical buyers.
• Experience selling into AI, security, financial services, healthcare, or insurance.
• Ability to generate pipeline and own outcomes end-to-end.

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.
• Learn and communicate technical concepts clearly to customers.
• Engage buyers in regulated industries such as financial services, healthcare, and insurance.
• Generate pipeline through inbound leads, conference networking, referrals, and outbound efforts.
• Maintain momentum through long, multi-stakeholder sales processes.
• Shape pilots and deployments with product and engineering feedback.

Skills

Enterprise software sales

AI security domain

Technical buyer engagement

Pipeline generation

Startup environment

Independent worker

Executive stakeholder engagement

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 https://www.grayswan.ai/about.

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

TYPICAL INTERVIEW PROCESS

• Application review. We read everything; we’ll respond within 10 days.
• Recruiter Screen. We learn about you; you learn about us.
• Technical interview or Hiring Manager Interview.
• Role related assessment
• Experience & culture interview
• Reference checks. We’ll reach out to 3-5 references that you provide.
• Offer. If it’s mutual, we move fast.