Personalized Life Assistant

Weekday (YC W21)

. Evaluate how well AI systems handle personalized, real-world life tasks .

Posted 9/18/2026contractRemote • United StatesMid-LevelSenior💰 $50 - $200 per hourWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in evaluating AI systems for personalized real-world tasks, with a focus on improving AI assistants' effectiveness and trustworthiness. Proficient in assessing AI outputs for quality and realism while utilizing various AI tools for multi-step decision-making and workflows.

Highest-signal resume keywords

Heavy Personal Usage Of LLM ProductsExperience Using AI For Multi-Step TasksFamiliarity With Tools Such As ChatGPTStrong Written JudgmentAttention To Detail

ATS Keywords

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Applicant Tracking System Keywords

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Tools & Technologies

ChatGPTClaudeGeminiPerplexityCursorWindsurfCodex

Industry Keywords

AI EvaluationPersonalizationTrustworthinessReal-World WorkflowsDecision-Making

About the role

Key responsibilities & impact

Evaluate how well AI systems handle personalized, real-world life tasks
Judge whether AI responses are useful, personalized, realistic, and successful
Evaluate AI support for practical, high-context tasks across food, health, productivity, careers, and learning
Help improve AI assistants’ personalization, trustworthiness, and usefulness for real-world personal workflows

Requirements

What you’ll need

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
Expected commitment of 20-40 hours/week
We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request