AI Product Operations Specialist - Freelance, Remote

About this role

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 structured, actionable feedback to the Head of Engineering and product/engineering teams Collect and synthesize feedback from other assistants/users; turn insights into prioritized improvements Critique internal software and propose data-backed enhancements to workflows and UX Technical Troubleshooting QA Triage broken workflows, diagnose likely failure points, and collaborate with engineers on root causes Consolidate deployment updates and confirm changes behave as expected in production Design lightweight test plans for ambiguous features; track outcomes and follow through to resolution Operational Support to the Head of Engineering Manage and organize the Head of Engineering’s to-do list; drive proactive follow-through across a 30+ person team Maintain and optimize work queues; ensure the right priorities are surfaced at the right time Handle calendar management via AI tools; coordinate with stakeholders as needed Systems Process Optimization Build simple, scalable processes in ambiguous environments; streamline task flows and handoffs Propose and implement improvements to reduce repeated failure modes and increase throughput Leverage AI productivity tools to automate routine steps and create operational leverage Skills, Knowledge and Expertise Required: Demonstrated technical mindset with strong AI tool fluency (e.g., ChatGPT, LLM workflows) or a programming background Proven experience in product operations, QA/Testing, technical support, or similar role working closely with engineers Exceptional written communication for clear, structured bug reports and product feedback Comfortable operating independently in ambiguous, fast-paced environments with minimal SOPs Availability to work 40 hours/week, Monday–Friday, 9:00 am–5:00 pm Eastern Time (may shift slightly earlier after 3–4 weeks) WFH Set-Up: Computer with at least 8GB RAM, an Intel i5 core processor/AMD Ryzen 5 Processor and up.