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Date Posted:
6/30/2025
Remote Work Level:
100% Remote
Location:
Remote from Anywhere
Job Type:
Freelance
Job Schedule:
Full-Time
Career Level:
Senior Level Manager (Director, Dept Head, VP, General Manager, C-level)
Travel Required:
No specification
Education Level:
Bachelor's/Undergraduate Degree
Salary:
We're sorry, the employer did not include salary information for this job.
Categories:
Business Development, Education & Training, Product Manager, Project Manager, Teaching, Operations
About the Role
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