Executive AI Trainer for Startup Leadership (Remote)

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

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.