AI Product Operations Specialist - Freelance, Remote

About the ClientThe hiring manager is the Head of Engineering, who partners closely with product team and iterate quickly on emerging LLM workflows. The culture values autonomy, candor, and high standards in a startup-paced environment. Why does this role exist? This role exists to serve as a highly autonomous right hand to the Head of Engineering, operating and stress-testing experimental AI tools while closing the feedback loop between users and the engineering/product teams. By proactively finding breakages, documenting issues, and prioritizing work across a 30+ person team, this role accelerates engineering velocity and product quality. It ensures the organization can scale experimentation, reduce failures in production, and maintain tight operational rhythms without relying on rigid SOPs. The Impact you’ll make AI Tool Operations Testing Operate, stress-test, and quality-check cutting-edge AI tools and LLM-based systems that may frequently break Reproduce edge cases, capture logs/screens, and write clear repro steps; file/track tickets in Shortcut (Clubhouse) Validate fixes and run smoke/regression tests before and after deployments Product Feedback Collaboration Provide stru…