Senior Sales Engineer (Pittsburgh)

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.

The Role

As a Senior Sales Engineer at Gray Swan, you will lead technical pre-sales for our AI security platform, serving as a trusted technical advisor to enterprise customers evaluating how to secure, govern, and deploy advanced AI systems in production.

You will partner closely with Account Executives on complex, high-value opportunities, owning the technical narrative from first discovery through close. This role requires deep technical credibility, strong commercial instincts, and the ability to translate sophisticated AI security risks into clear, differentiated solutions for both technical and executive audiences.

This is a hands-on, customer-facing role operating in high-stakes, fast-moving environments where buyers are often defining their AI security posture for the first time.

What You’ll Do:

Pre-Sales Technical Leadership

• Serve as the technical lead on enterprise sales opportunities, partnering with Account Executives to shape deal strategy and execution.

• Lead technical discovery with customer security, AI, and platform teams to understand architectures, threat models, and operational constraints.

• Define technical win strategies, including solution design, evaluation plans, and success criteria.

• Act as a trusted technical advisor to senior customer stakeholders throughout the buying process.

AI Security Expertise & Solution Design

• Articulate and demonstrate how the Gray Swan platform identifies vulnerabilities in and protects modern AI systems.

• Design deployment architectures for integrating Gray Swan across development, deployment, and runtime environments.

• Advise customers on best practices for AI security, governance, and operationalization.

Demos, POCs, & Technical Validation

• Design, build, and maintain compelling demo environments tailored to customer use cases.

• Lead proofs of concept and pilots that clearly demonstrate value and differentiation.

• Address deep technical, architectural, and security objections with confidence and authority.

• Support security reviews, threat modeling sessions, and technical due diligence.

Executive & Technical Communication

• Communicate complex AI security concepts clearly to engineers, security leaders, and executives.

• Translate technical capabilities into measurable business impact and risk reduction.

• Support RFPs, security questionnaires, and compliance discussions.

• Represent Gray Swan as a technical authority in customer meetings and select industry forums.

Cross-Functional Collaboration

• Provide structured feedback to Product and Engineering based on real-world customer needs.

• Surface patterns across enterprise buyers to influence roadmap prioritization.

• Contribute to technical sales enablement and internal knowledge sharing.
  

What You Bring:

• 7–12+ years of experience in sales engineering, solutions engineering, security engineering, technical consulting, or related roles.

• Strong understanding of modern AI/ML systems, including LLM-based applications and agentic architectures.

• Solid grounding in security concepts such as threat modeling, monitoring, detection, and response, with the ability to reason about adversarial systems.

• Familiarity with cloud-native architectures (AWS, GCP, Azure), APIs, distributed systems, and enterprise platforms, including on-prem deployments.

• Prior experience supporting or selling security, infrastructure, AI, or developer platforms.

• Proven experience engaging with CISOs, security architects, ML engineers, and platform leaders.

• Track record supporting complex, multi-stakeholder enterprise deals.
  

You’ll Thrive Here If You:

• Have an entrepreneurial mindset and enjoy working at an early-stage, high-growth startup.

• Want to help shape how Gray Swan sells and positions its platform in the enterprise market.

• Enjoy working directly with customers and excel at demos, storytelling, and problem-solving.

• Are motivated by Gray Swan’s mission to make AI systems safer and more trustworthy.

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.

Compensation: $115,000-$135,000 + commissions and a competitive equity package in a startup with real revenue and globally recognized customers

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

• Visa sponsorship available for exceptional candidates