Chief Executive Specialist (AI)

TL;DR

Chief Executive Specialist (AI Trainer): Train advanced language models on small business leadership, early-stage startup growth, product-market fit discovery, and strategic planning with an accent on bootstrapping, venture funding, go-to-market strategies, and founder decision-making. Focus on conversing with models on business scenarios, verifying strategic reasoning accuracy, capturing error traces, and suggesting prompt engineering improvements.

Remote (United States of America)

$8-$65 per hour (varies by experience, expertise, and geographic location)

Company

hirify.global builds high-quality training data to evolve large language models into strategic leadership engines for entrepreneurs and founders.

What you will do

• Converse with AI models on business-building scenarios and theoretical leadership questions.
• Verify practical accuracy and strategic reasoning in model responses.
• Capture reproducible error traces and document failure modes.
• Suggest improvements to prompt engineering and evaluation metrics.

Requirements

• Experience founding, co-founding, or leading a small business, nonprofit, or early-stage startup, wearing multiple hats in strategy, finance, hiring, and operations.
• Strong knowledge of bootstrapping vs. venture funding, go-to-market strategies, founder equity splits, operational budgeting, early hiring, leadership philosophy, and lean startup methodology.
• Bachelor’s degree in business, economics, or related field (strong signal, not required).
• Clear, metacognitive communication skills—showing your work.
• Secure computer and high-speed internet (as contractor).

Nice to have

• Familiarity with startup accelerators, small business management tools, fundraising decks, and real-world P&L decision-making.

Culture & Benefits

• Freelance contractor role with flexible pay based on expertise.
• No company-sponsored benefits like health insurance or PTO.
• Opportunity to shape future AI capabilities in leadership and business judgment.