Freelance AI Trainer for Small Business

About the Role: Freelance AI Trainer for Small Business

Are you a current or former small business owner eager to shape the future of AI? Large-scale language models are evolving from simple conversational tools into systems capable of supporting entrepreneurs with operations, strategy, financial planning, and customer engagement. With high-quality training data grounded in real-world business experience, tomorrow’s AI can better serve Very Small Business (VSB) owners navigating limited resources and high-stakes decisions. That training data begins with you—we need your practical expertise to help power the next generation of AI.

We’re looking for current or former owners and co-owners across a range of industries, including retail, e-commerce, professional services such as consulting, legal, and accounting, technology and software, hospitality and food and beverage, healthcare and wellness, creative and media, construction and trades, and other small business sectors. Whether you are a new business owner or have years of operational experience, your insight into day-to-day decision-making is highly valuable.

What You'll Do

• Engage the model with realistic small business scenarios and operational challenges.
• Evaluate outputs related to budgeting, pricing, marketing strategy, hiring decisions, vendor management, customer communications, and basic compliance considerations.
• Assess whether responses are practical and aligned with how Very Small Businesses actually operate.
• Capture reproducible error traces and provide structured feedback to improve prompts, evaluation criteria, and real-world applicability.
• Help identify where models oversimplify trade-offs or misunderstand resource constraints common to VSB environments.

What We're Looking For

• Direct experience owning or co-owning a small business is strongly preferred.
• Experience managing operations, finances, marketing, staffing, or growth strategy is highly relevant.
• Entry-level business owners as well as seasoned entrepreneurs are encouraged to apply.
• Clear, metacognitive communication—explicitly articulating how and why decisions are made in a real business context—is essential.

Ready to turn your small business ownership experience into the knowledge foundation for tomorrow’s AI? Apply today and help train systems that better support entrepreneurs worldwide.

Compensation and Benefits

We offer a pay range of $6 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.

Key skills/competency

• Small Business Operations
• AI Training
• Entrepreneurial Experience
• Strategic Planning
• Financial Management
• Marketing Strategy
• Customer Engagement
• Problem Solving
• Feedback Loop Optimization
• Communication Skills