Chief Executives - Freelance AI Trainer Project

Job Summary

We're seeking chief executives with expertise in small business leadership, startup growth, and strategic planning to train large-scale language models. Your insights will help democratize world-class leadership and support entrepreneurs.

Responsibilities

• Challenge advanced language models on topics like bootstrapping vs. venture funding, go-to-market strategies, founder equity splits, operational budgeting, early hiring decisions, leadership philosophy, and lean startup methodology.
• Document every failure mode to improve model reasoning.
• 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.

Requirements

• A bachelor’s degree in business, economics, or a related field (though not required).
• Experience founding, co-founding, or leading a small business, nonprofit, or early-stage startup.
• Familiarity with startup accelerators, small business management tools, fundraising decks, and real-world P&L decision-making.
• Clear, metacognitive communication skills.

Qualifications

• Expertise in business, economics, or a related field.
• Experience in leadership roles within small businesses, startups, or nonprofits.

Skills

• Strong verbal and written communication skills.
• Experience with business-building scenarios and theoretical leadership questions.
• Ability to document and explain failure modes.
• Knowledge of startup accelerators, small business management tools, fundraising decks, and P&L decision-making.

Benefits

Pay range: $6-$65 per hour, with final rates determined based on experience, expertise, and location.

Contractor provides their own secure computer and high-speed internet.

No company-sponsored benefits such as health insurance or PTO.

Pay

$6-$65 per hour

Schedule

Remote work

Seniority Level

Mid - Senior Level