Chief Executives

Title: Chief Executives - AI Trainer

Location: World Wide - Remote

Job Description:

 

Are you a chief executive expert eager to shape the future of AI? Large-scale language models are evolving from clever chatbots into powerful engines of strategic and organizational insight. With high-quality training data, tomorrow's AI can democratize world-class leadership, scale sound business judgment, and support entrepreneurs and founders in building successful ventures. That training data begins with you-we need your expertise to help power the next generation of AI.

 

We're looking for chief executive specialists who live and breathe small business leadership, early-stage startup growth, product-market fit discovery, strategic planning, financial oversight, team building, and founder decision-making. You'll 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-documenting every failure mode so we can harden model reasoning.

 

On a typical day, you will converse with the model on business-building scenarios and theoretical leadership questions, verify practical accuracy and strategic reasoning, capture reproducible error traces, and suggest improvements to our prompt engineering and evaluation metrics.

 

A bachelor's degree in business, economics, or a related field is a strong signal, though not required. Ideal candidates have experience founding, co-founding, or leading a small business, nonprofit, or early-stage startup-especially where you've worn 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 are all strong indicators of fit. Clear, metacognitive communication-"showing your work"-is essential.

 

Ready to turn your leadership experience into the knowledge base for tomorrow's AI? Apply today and start teaching the model that will teach the world.

 

We offer a pay range of $8-to-?$65 per hour, with the exact rate determined after evaluating your experience, expertise, and geographic location. Final offer amounts may vary from the pay range listed above. As a contractor you'll supply a secure computer and high-speed internet; company-sponsored benefits such as health insurance and PTO do not apply.

 

Job title: Chief Executive Specialist - AI Trainer
Employment type: Contract
Workplace type: Remote
Seniority level: Mid - Senior Level