Chief Underwriting Officer

DataAnnotation is committed to creating high-quality AI. We are looking for a Chief Underwriting Officer to join our team to help train the next generation of AI while enjoying the flexibility of remote work and the freedom to set your own schedule. This role is designed to fit a variety of lifestyles — whether you’re looking to contribute part-time alongside a current position, pursue it full-time, or engage periodically as a flexible professional opportunity.

Role

• Review and improve AI Assistant answers to questions about macro trends, corporate finance, and capital markets
• Leverage your education and work experience to check the reasoning and accuracy of an AI Assistant's work
• Push the models with complex, real-world scenarios and edge cases to see where their reasoning holds up – and where it doesn’t.
• Share clear, structured feedback to help make each new version of the AI smarter and more reliable.

To succeed in this position, you should have expert-level financial reasoning and formal training in a finance-related discipline. A Master’s or PhD (completed or in progress) is strongly preferred. Relevant backgrounds include Financial Accounting, Investment Banking, Corporate Development, Wealth Management, and Insurance Planning.

Benefits

• This is a full-time or part-time REMOTE position
• You’ll be able to choose which projects you want to work on
• You can work on your own schedule
• Projects are paid hourly starting at USD $50-$60 per hour, with bonuses on high-quality and high-volume work

Responsibilities

• Give AI chatbots diverse and complex problems and evaluate their outputs
• Evaluate the quality produced by AI models for correctness and performance

Qualifications

• Fluency in English (native or bilingual level)
• Detail-oriented
• Proficient in financial analysis, financial modeling, data analysis, and other reasoning exercises related to finance management
• A current, in progress, or completed Masters and/or PhD is preferred but not required

Note: Payment is made via PayPal. We will never ask for any money from you. PayPal will handle any currency conversions from USD. Only applicants in United States will be considered for this role. This is an independent contract position.