Introducing the Gray Swan AI Proving Ground: The Fastest Path to AI Red Teaming Careers

Introducing the Gray Swan AI Proving Ground: The Fastest Path to AI Red Teaming Careers

Gray Swan
June 24, 2025

Starting June 25th, Gray Swan is launching Proving Ground: a new system of weekly AI red teaming challenges designed to help participants build skills, demonstrate expertise, and open real career doors.

Over the past year, Gray Swan Arena has become one of the leading proving grounds for AI red teaming talent:

• 10+ contractors hired directly from Arena participants
• Multiple full-time hires
• Interns brought into our internal research teams
• Over $370K paid out to red-teamers across global challenges

Proving Ground expands this pipeline.

Every week, participants will tackle expert-designed challenges across:
• Jailbreaking & prompt injection
• Multimodal vision exploits
• Agent manipulation & tool abuse
• Dangerous reasoning & chain-of-thought attacks

Why it matters:

Proving Ground isn’t a course or a certification. It’s real, applied attack simulation on the types of failure modes frontier AI labs need to understand today. Each successful break contributes to your personal profile with verifiable metrics, sharable achievements, and expert-backed credibility that leading AI companies are already paying attention to.

At Gray Swan, we’ve already hired directly from our Arena. Our sponsors, partners, and research labs are actively watching these results. Proving Ground gives participants a way to build not just skills, but visibility.

New challenges drop every Wednesday, starting June 25.

Whether you're an AI researcher, cybersecurity professional, student, or curious newcomer this is where you build experience that matters.