Chief Information Officer - AI Trainer

DataAnnotation is committed to creating high-quality AI. We are looking for a CIO 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. We’re currently expanding into an exciting new area – teaching AI Assistant models to be a more useful tool for finance professionals. We’re seeking experienced finance professionals with advanced degrees (MBA+) and professional experience to use their expertise to help shape how AI understands financial principles and decision-making. You Might 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. 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-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 the United States will be considered for this role. This is an independent contract position. #J-18808-Ljbffr