Job Overview
Location
Pittsburgh
Job Type
Full-time
Category
Sales
Date Posted
March 21, 2026
Full Job Description
📋 Description
- • As an Enterprise Account Executive at Gray Swan AI, you will own end-to-end enterprise sales cycles for a cutting-edge AI safety and security platform, engaging technical and executive stakeholders in high-stakes industries such as financial services, healthcare, and insurance to drive paid pilots and long-term production deployments.
- • You will build credibility with AI, security, and engineering teams by learning and communicating complex technical concepts clearly, collaborating closely with founders, product, and engineering to shape customer solutions and provide field feedback that influences product direction and go-to-market strategy.
- • Gray Swan AI is a well-funded, fast-growing team of ~25 people protecting organizations from emerging AI security threats through real-time threat detection, automated validation, and adaptive defenses, offering meaningful equity and real responsibility from day one in a mission-driven environment focused on practical AI safety impact.
- • You will generate pipeline through inbound leads, conference networking, referrals, and outbound efforts, partnering with the SDR team to convert interest into qualified opportunities while maintaining momentum through long, multi-stakeholder sales processes and owning outcomes with high autonomy and initiative.
- • This role offers the opportunity to help define how enterprise AI safety and security software is sold, work on hard problems in a new and rapidly evolving market, and close meaningful six-figure deals with significant upside, all while being motivated by ownership, accountability, and the chance to contribute beyond a narrowly defined sales role in an early-stage startup.
🎯 Requirements
- • 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 without an engineering background.
- • 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 in early-stage startup environments.
- • Highly motivated, disciplined, and willing to work hard to build something meaningful with presence, credibility, and sound judgment in customer interactions.
🏖️ Benefits
- • Competitive base salary targeted at $90,000-$140,000 + commissions ($190-240K OTE)
- • Meaningful equity participation
- • 401k with up to 4% matching
- • 28 days annual leave (vacation + holidays)
- • Health, dental, and vision coverage
- • Catered lunches (Pittsburgh office)
- • Flexible work arrangements (office or remote)
Skills & Technologies
About Gray Swan AI
Gray Swan AI is a technology company focused on developing and deploying artificial intelligence solutions. They specialize in creating AI-powered tools and platforms designed to address complex challenges across various industries. Their offerings often involve advanced machine learning, natural language processing, and data analytics to provide actionable insights and automate processes. Gray Swan AI aims to help organizations leverage the power of AI to improve efficiency, drive innovation, and gain a competitive edge. The company's approach typically involves a deep understanding of client needs to deliver tailored AI strategies and implementations that yield measurable results and foster long-term growth.
Subscribe to the weekly newsletter for similar remote roles and curated hiring updates.
Newsletter
Weekly remote jobs and featured talent.
No spam. Only curated remote roles and product updates. You can unsubscribe anytime.
