Chief Executives - AI Trainer

Remote; San Francisco (CA); Remote; USD 11,000 - 90,000; Full time

Job summary

Remote seeks a Chief Executive Specialist – AI Trainer to help shape the future of AI leadership. You’ll test model reasoning on startup strategy topics, discuss funding, go-to-market plans, and lean operations. A business background is valued, with founder-level experience as a strong signal.

As a contractor, you will work remotely, engaging with the model daily, documenting failures, and proposing improvements to prompts and evaluation metrics based on real-world P&L decisions.

Qualifications

• Experience leading a small business, nonprofit, or early-stage startup.
• Strong strategic planning and financial oversight abilities.
• Clear, metacognitive communication and ability to show reasoning.

Responsibilities

• Advise on business-building scenarios and leadership questions to test model reasoning.
• Verify practical accuracy and document reproducible error traces.
• Suggest improvements to prompt engineering and evaluation metrics.
• Collaborate with AI researchers to refine startup-focused frameworks.

Skills

Leadership in small business/startups

Strategic planning

Financial oversight

Clear communication (metacognitive)

Education

Bachelor's degree in business or economics

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?

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