AI Chatbot Evaluation Specialist for Small Business Scenarios

About the role

We are looking for a freelance specialist to evaluate AI chatbot responses in realistic small‑business scenarios. You will compare multiple AI assistants, judge the quality of their answers, and provide structured feedback that helps improve our AI products.

Key responsibilities

• Create realistic business‑related prompts based on defined user goals.
• Interact with up to five AI chatbots per conversation, limited to five turns each.
• Assess each response for clarity, usefulness and accuracy.
• Submit conversation transcripts, evaluation results and comparative analysis.
• Use supporting files such as spreadsheets, PDFs and images during the evaluation process.

Required profile

• Current or former small‑business owner, or strong understanding of small‑business operations.
• Strong analytical and critical‑thinking abilities.
• Ability to follow detailed evaluation guidelines.
• Comfortable working with AI tools and remote collaboration.

Required skills

• Proficiency with spreadsheet software (e.g., Microsoft Excel).
• Experience handling PDF documents.

What we offer

• Fully remote, flexible schedule.
• Project‑based contract lasting 10 weeks.
• Opportunity to work at the forefront of AI applications in business.