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Remote Real Estate Investment Associate - AI Trainer ($50-$60 per hour)
Mundelein, ILMarch 28th, 2026
DataAnnotation is committed to creating high-quality AI. 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.
We're growing a team of finance experts, and as the team grows, so will your opportunities. In this role, 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.
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 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. This is an independent contract position.
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