AI Product Operations Specialist - Freelance, Remote

The Impact you’ll make

• 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

• 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

• 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

• 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

• 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

• 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)

• Computer with at least 8GB RAM, an Intel i5 core processor/AMD Ryzen 5 Processor and up.
• Internet speed of at least 40MBPS
• Headset with an extended mic that has noise cancellation and a webcam
• Back-up computer and internet connection
• Quiet, dedicated workspace at home

• Technical: AI tool proficiency; systems thinking; test design and execution; QA methodologies; debugging mindset; clear documentation; comfort with Shortcut (Clubhouse), GSuite, Slack, and experimental internal tools (e.g., Magic AI); familiarity with messaging tools (e.g., Messenger). Bonus: basic scripting/automation, product analytics literacy.
• Operational: Task prioritization; work queue management; lightweight process design; deployment update consolidation; calendar management via AI.
• Behavioral: Proactive ownership; “figure it out” mentality; high attention to detail; resilience when tools break; curiosity and growth mindset; comfort giving candid, constructive feedback; ability to work independently and collaboratively with engineers.

• You love being an early power user of new AI tools, enjoy breaking things to make them better, and can translate ambiguous symptoms into actionable engineering feedback.
• You thrive in uncertainty, don’t need handholding, and naturally create order and leverage through systems and process improvements.
• You communicate crisply in writing, challenge assumptions respectfully, and partner well with engineers and product managers.
• You want to grow at the intersection of AI operations, product testing, and systems thinking. Bonus: You’re in a LATAM timezone for strong overlap with EST, and/or you have experience in programming, product, or data analytics.

Benefits

Originally posted on Himalayas