Gray Swan, the AI security startup headquartered on Ellsworth Avenue in Shadyside, has closed a $40 million Series A, cementing Pittsburgh's growing standing as a hub for responsible artificial intelligence. The round, announced on May 28, was co-led by Wing Venture Capital of California and Madrona of Seattle, with additional backing from Obvious Ventures, Snowflake Ventures, Hudson River Trading, Samsung Next, and Pittsburgh's own Magarac Venture Partners.

The company was founded in 2023 as a spinout from Carnegie Mellon University by CEO Matt Fredrikson and Chief Scientist Zico Kolter, two researchers who spent their careers studying the vulnerabilities that can lurk inside even the most capable AI models. Their thesis: as companies race to deploy AI across critical operations, the question of whether those systems will behave safely and predictably has never been more urgent. Gray Swan was built to answer it.

The company's platform runs on three interconnected tools. Shade tests AI models for weaknesses before they ever go live, probing for the failure modes that standard benchmarks miss. Cygnal monitors and blocks dangerous behavior in real time once a model is deployed. And Arena, the most novel piece of the stack, is a global network of more than 15,000 ethical hackers who continuously probe AI systems for newly discovered vulnerabilities, feeding both tools with up-to-date threat intelligence. Together, the platform gives enterprise customers something that has been in short supply: confidence that their AI infrastructure will perform safely under real-world conditions.

That value proposition has attracted serious attention from the industry's most prominent players. Gray Swan's work has been cited in published reports from Anthropic, OpenAI, and Meta, and the company currently counts more than 20 customers across frontier AI labs and global enterprises. Snowflake, whose venture arm participated in the Series A round, is among them.

Built in Pittsburgh, Cited Worldwide

The raise comes after a measured early journey. Gray Swan had previously secured $5 million in 2024 and another $5 million in 2025, building its platform and customer base before pursuing institutional scale. The $40 million round marks a significant step up, one that Fredrikson says will go toward accelerating go-to-market operations, deepening partnerships with frontier labs, and scaling the team in Shadyside. The company is currently hiring across engineering, sales, and marketing, with roles paying up to $260,000 annually.

"Our mission is to empower the world to use AI safely and securely," Fredrikson said in the announcement, "and this funding lets us pursue the mission on pace with the frontier."

For Pittsburgh, the Gray Swan story is a familiar one told at an unfamiliar scale. The city has been spinning out AI and robotics companies from Carnegie Mellon for decades, but the latest generation of CMU-rooted ventures is raising at figures that would have seemed improbable even five years ago. Earlier this year, Skild AI, another CMU spinout focused on general-purpose robotics, raised $1.4 billion in a single round. Gray Swan's raise, while smaller in absolute terms, is notable for its focus on the AI safety question that is increasingly preoccupying every major technology company in the world.

Technical.ly named Gray Swan the top company on its 2026 RealLIST Startups in Pittsburgh, a recognition that reflects not just the company's funding trajectory but the quality of research underpinning its products. For a city that has long leveraged its university talent into commercial ventures, Gray Swan represents exactly the kind of high-value, knowledge-intensive business Pittsburgh has spent years cultivating in its innovation corridors. With $40 million in fresh capital and a roster of marquee customers, the Shadyside startup is well-positioned to carry that tradition forward on one of technology's defining challenges.