Remote Personalized Assistant Expert - AI Trainer

About the Opportunity

A leading AI research organization is seeking advanced LLM power users to evaluate how well AI systems handle personalized, real‑world life tasks. This role is for people who use AI tools heavily in their personal lives and can clearly judge whether an AI response is useful, personalized, realistic, and successful.

• Create written responses and explanations for complex personal tasks
• Judge whether outputs are practical, well‑reasoned, and appropriately personalized
• Identify where the AI succeeds, fails, overreaches, or misses important context
• Apply structured rubrics and quality criteria to assess model performance
• Use your own LLM experience to evaluate real‑world usefulness

• Heavy personal usage of LLM products
• Experience using AI for multi‑step tasks, planning, research, decision‑making, or personal workflows
• Familiarity with tools such as ChatGPT, Claude, Gemini, Perplexity, Cursor, Windsurf, Codex, or other AI agents
• Ability to explain what makes an AI output good, bad, incomplete, unsafe, or unrealistic
• Strong written judgment and attention to detail
• Experience writing and evaluating against rubrics is extremely critical
• Extensive rubric experience, including 100+ hours on prior rubric projects involving rubric design, evaluation, and quality assessment

Finding restaurants, booking tables, choosing delivery options, comparing menus, and accounting for dietary preferences, budget, location, occasion, timing, and group needs.

Reasoning through personal health questions, reviewing Apple Health or wearable data, identifying trends in sleep, activity, heart rate, or blood pressure, and knowing when medical guidance is needed.

Managing life admin, personal projects, errands, reminders, household tasks, calendars, follow‑ups, and personal CRM systems.

Finding and applying to jobs, editing resumes or Linked In profiles, preparing outreach, networking, using Linked In for advancement, and planning career moves.

Creating study plans, learning roadmaps, accountability systems, skill‑building plans, and personalized development goals.

LLMs are quickly becoming personal assistants for everyday decisions, but truly useful AI needs to do more than produce generic advice. It needs to understand context, preferences, constraints, tradeoffs, and what success looks like in real life. Your evaluations will help improve how AI systems support people with practical, high‑context tasks across food, health, productivity, careers, and learning. This work directly contributes to making AI assistants more personalized, trustworthy, and useful for real‑world personal workflows.

Expected commitment: 15–40 hours/week.

Work Trial:
Participants will be asked to complete a paid work trial as part of the onboarding process for this project. The work trial pays $30 after completion and is designed to help assess each participant’s fit for the role based on LLM experience and domain expertise. We recommend putting thoughtful effort into the assessment, as it will play a significant role in the selection process.
Please note that the project is still in its early stages, and so please expect an initial delay in getting started or tasking.

Participants will write clear, realistic prompts for complex personal‑life tasks, execute those tasks while recording their screens, and create detailed evaluation rubrics to assess how well AI systems perform. This work requires both strong ChatGPT power‑user experience and firsthand expertise completing challenging, research‑intensive personal workflows end‑to‑end.

You should be able to turn around tasks within 24 hours.

A desktop or laptop computer is required (Chromebooks are not supported).