Remote AI Evaluation Analyst - Small Business Ops

Crossing Hurdles; United States; On-site; USD 35,817,600 - 39,950,400; Full time

Job summary

Crossing Hurdles is seeking a Small Business Owners AI (English - US) contractor to help evaluate AI prompts across real-world small business scenarios. This remote, 16-week assignment requires up to 40 hours per week with a 4-hour overlap with PST.

You will interact with multiple AI chatbots, rate outputs for accuracy, clarity, relevance, and usefulness, and provide structured feedback using business documents, spreadsheets, PDFs, and images. Prior small business ownership is essential.

Qualifications

• Experience as a small business owner or in managing business operations.
• Strong understanding of day-to-day business workflows, customer management, and financial planning.
• English-language business documents for evaluation tasks.
• Strong analytical, critical thinking, and written communication skills.
• Comfortable with AI tools and following evaluation guidelines.
• Available to work up to 40 hours per week with 4-hour overlap with PST.

Responsibilities

• Create realistic prompts based on day-to-day small business scenarios.
• Interact with multiple AI chatbots and evaluate their responses.
• Compare AI outputs for accuracy, clarity, relevance, and usefulness.
• Provide structured feedback and submit evaluation results.
• Use business documents, spreadsheets, PDFs, images, and other files during evaluations.
• Complete assigned project tasks while following evaluation guidelines.

Skills

Analytical

Critical thinking

Written communication

AI tool familiarity

Tools

AI tools

Job description

Crossing Hurdles is seeking a Small Business Owners AI (English - US) contractor to help evaluate AI prompts across real-world small business scenarios. This remote, 16-week assignment requires up to 40 hours per week with a 4-hour overlap with PST.

You will interact with multiple AI chatbots, rate outputs for accuracy, clarity, relevance, and usefulness, and provide structured feedback using business documents, spreadsheets, PDFs, and images. Prior small business ownership is essential.