Chief Executive Specialist – AI Trainer

Greenhouse

Salary range

$8–$65/year

Benefits

Job Description

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. 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. 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.
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