Small Business Chatbot Evaluator

About OpenTrain

OpenTrain is the #1 platform for building careers in AI training and data labeling. We connect people with project-based work that helps shape how AI systems behave and grow a durable freelance portfolio under one account.

As the hiring and contracting organization for this role, OpenTrain AI runs projects that are remote, flexible, and designed for contributors who want hands-on experience training generative models.

About AI training work

AI training (data labeling/annotation and human feedback) is the human layer that teaches models to answer helpfully and reliably. Tasks include writing prompts, holding short conversations, judging model outputs, and producing structured feedback.

This role focuses on RLHF-style evaluation and comparative rating: you will run conversations, judge responses for clarity and usefulness, and submit transcripts and ratings that directly influence model behavior.

The role

OpenTrain AI is recruiting a Small Business AI Chatbot Evaluator to review and compare chatbot outputs across realistic small business scenarios. Work is project-based and centered on judgment, accuracy, and clear critique.

This is an entry-level, contractor, part-time role that requires a minimum commitment of 20+ hours per week, fluency in English, and the ability to follow structured evaluation guidelines. This work is open worldwide.

• Label types: RLHF and evaluation rating (comparative judgments).
• Data type: text; you will work with spreadsheets, PDFs, images, and business materials supplied per task.

What you'll do

You will create realistic business prompts, run short multi-turn chatbot conversations, and compare responses from multiple models. Each task includes clear instructions and a template for submitting transcripts and ratings.

• Design realistic prompts that reflect defined small business goals and constraints.
• Conduct multi-turn chatbot conversations and capture full transcripts.
• Compare and rate responses for clarity, usefulness, accuracy, and appropriateness.
• Submit structured evaluations with comparative feedback and supporting materials.
• Work with business documents such as spreadsheets, invoices, PDFs, and images when scenarios require them.

Requirements

Candidates must demonstrate a strong understanding of small business operations and the ability to follow evaluation guidelines closely. You do not need prior AI training experience, but you must be comfortable using AI tools in a structured workflow.

• Strong understanding of small business operations and common workflows.
• Ability to create realistic, goal-driven business prompts.
• Comfort evaluating chatbot responses for clarity, usefulness, and accuracy.
• Strong analytical and critical thinking skills.
• Ability to follow structured evaluation instructions and submit clear transcripts and ratings.
• Fluency in English (all project materials and submissions are in English).

Who should apply

This role is a good fit for people with hands-on small business experience, business analysts, operators, customer support leads, or anyone who understands how small businesses make decisions and use tools in practice.

• Current or former small business owners or operators.
• People with backgrounds in accounting, finance, marketing, or customer operations.
• Analytical thinkers who enjoy making clear, evidence-based judgments.
• Workers seeking flexible, remote, part-time contract work that builds AI training experience.

How it works

You will apply and work through your OpenTrain account. Tasks are assigned as projects and include detailed instructions, example prompts, and templates for transcripts and ratings. Expect to review multiple chatbot responses per task and submit structured comparative feedback.

This is contractor, part-time work requiring 20+ hours per week. OpenTrain handles onboarding and project details; payment and task-specific compensation are provided through the platform during the application/onboarding process.

• Worldwide applicants accepted; project language and deliverables are in English.
• Contractor role with flexible scheduling—fit work around other commitments.
• Onboarding includes training on evaluation guidelines and examples.