Gray Swan, a Pittsburgh-based AI security startup and Carnegie Mellon spinout, announced a $40 million Series A led by Wing Venture Capital and Madrona, with participation from Snowflake Ventures, Hudson River Trading, Samsung Next and Magarac Venture Partners.

As AI agents become more capable and tools and data expand, the surface for attacks grows, prompting proactive red-teaming and continuous testing as core defenses.

Bettridge, a Blizzard Entertainment security engineer, has competed in more than 1,000 challenges through Arena in the past year, highlighting growing professional engagement in AI safety testing.

CEO and cofounder Matt Fredrikson says the mission is to enable safe and secure AI deployment at scale.

OpenAI was an early customer testing jailbreaks on its o1 models; Kolter sits on the OpenAI Foundation board, underscoring Gray Swan’s deep ties to major AI labs and emphasis on safety and governance.

New funding will accelerate go-to-market efforts, deepen partnerships with frontier labs, and scale the team.

Gray Swan counts over 20 customers across frontier labs and global enterprises, including Snowflake, among its clients.

Founded in 2023 by CMU professors Matt Fredrikson and Zico Kolter, Gray Swan has become a key security provider for leading labs and contributes to frontier model risk assessments used in system cards for models like GPT-5 and Mythos.

Products include Shade, an AI agent that actively probes vulnerabilities, and Cygnal, a real-time monitoring tool that blocks harmful prompts and tool access, leveraging human red-team data to bolster defenses.

The platform also encompasses Arena, a network of more than 15,000 ethical hackers providing ongoing threat intelligence.

The company is based in Pittsburgh’s Shadyside, actively hiring across engineering, sales, and marketing, with salaries up to $260,000.

Technical.ly named Gray Swan the top startup on its 2026 RealLIST Pittsburgh.