Remote Personalized AI Assistant Evaluator

OpenTrain AI; Northern (KY); Hybrid; USD 69,000 - 276,000; Part time

Benefits offered by this job

Remote contract

Flexible schedule

20–40 hours per week

Job summary

OpenTrain AI is recruiting a Personalized AI Assistant Evaluation Expert to assess how well AI systems handle practical, high-context personal tasks. You will review responses involving food, health, productivity, careers, and learning, then determine whether each output is useful, realistic, trustworthy, and successful for the situation.

The role is remote contract work in the United States with a 20–40 hours per week commitment, a flexible schedule, and compensation between $50 and $200 per

Qualifications

• This is an entry-level opportunity for candidates with substantial hands-on experience using modern AI products.
• Ability to reason about context, preferences, constraints, tradeoffs, and intended outcomes, then defend nuanced judgments in clear written explanations.
• Strong written reasoning about context, preferences, constraints, tradeoffs, and intended outcomes.
• Heavy personal use of large language model products and AI agents.
• Experience using AI for multi-step planning, research, decision-making, or personal workflows.
• Ability to assess whether responses are useful, realistic, complete, safe, and personalized.

Responsibilities

• Evaluate responses to multi-step tasks, planning requests, research questions, decisions, and personal workflows.
• Judge whether answers are accurate in context, complete, safe, realistic, and appropriately personalized.
• Explain what makes an AI output effective, incomplete, unsafe, generic, or impractical.
• Compare response quality and identify important gaps.
• Provide practical feedback that supports more useful and dependable personal AI assistance.

Skills

Heavy personal use of AI products

Experience with multi-step planning

Strong written reasoning

Attention to detail

Tools

ChatGPT

Claude

Gemini

Perplexity

Cursor

Windsurf

Codex

Job description

OpenTrain AI is recruiting a Personalized AI Assistant Evaluation Expert to assess how well AI systems handle practical, high-context personal tasks. You will review responses involving food, health, productivity, careers, and learning, then determine whether each output is useful, realistic, trustworthy, and successful for the situation.

The role is remote contract work in the United States with a 20–40 hours per week commitment, a flexible schedule, and compensation between $50 and $200 per