Chief Executives - Freelance AI Trainer Project

The role

You will converse with language models on business-building scenarios and theoretical leadership questions. You will verify practical accuracy and strategic reasoning, capture error traces, and suggest improvements to prompt engineering and evaluation metrics.

What you will do

• Converse with the model on business-building scenarios and theoretical leadership questions
• Verify practical accuracy and strategic reasoning
• Capture reproducible error traces
• Suggest improvements to prompt engineering and evaluation metrics
• Challenge advanced language models on topics like bootstrapping vs. venture funding, go-to-market strategies, founder equity splits, operational budgeting, early hiring decisions, leadership philosoph

Required qualifications

• Clear, metacognitive communication

Nice to have

• Bachelor’s degree in business, economics, or a related field
• Experience founding, co-founding, or leading a small business, nonprofit, or early-stage startup
• Experience wearing multiple hats across strategy, finance, hiring, and operations
• Familiarity with startup accelerators, small business management tools, fundraising decks, and real-world P&L decision-making

Before you apply

• As a contractor you’ll supply a secure computer and high-speed internet

About the company

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