AI Product Operations Specialist - Freelance, Remote

About the role

The Head of Engineering is looking for a highly autonomous AI Product Operations Specialist to operate, stress‑test and improve experimental AI tools. Working remotely, you will act as the right‑hand to the engineering lead, closing the feedback loop between users and the product team.

Key responsibilities

• Operate, stress‑test and quality‑check cutting‑edge AI and LLM‑based systems, reproducing edge cases and filing tickets in Shortcut (Clubhouse).
• Provide structured, actionable feedback to engineering and product teams, turning user insights into prioritized improvements.
• Triage broken workflows, diagnose failure points, run smoke/regression tests and validate fixes before and after deployments.
• Manage the Head of Engineering’s to‑do list, work queues and calendar, ensuring the right priorities surface for a 30‑plus person team.
• Design lightweight test plans, build simple scalable processes and automate routine steps using AI productivity tools.

Required profile

• Enjoy being an early power‑user of new AI tools, love breaking things to make them better, and can translate ambiguous symptoms into clear engineering feedback.
• Thrive in fast‑paced, ambiguous environments with minimal SOPs and take proactive ownership of tasks.
• Communicate crisply in writing, give candid constructive feedback and collaborate closely with engineers and product managers.

Required skills

• Fluency with AI tools such as ChatGPT and LLM workflows.
• Experience in product operations, QA/testing or technical support.
• Familiarity with Shortcut (Clubhouse), GSuite, Slack and internal experimental tools.
• Basic scripting/automation and product analytics literacy are a plus.