Small Business Owner - AI Evaluation Specialist (Remote, $17/hr)

Small Business Owner – AI Evaluation Specialist (Remote, $17/hr)

Remote – U.S. Only | 40 Hours/Week | $17/hour | 16-Week Contract

Job Overview:

We are hiring Small Business Owners and experienced small business professionals to work as AI Evaluation Specialists on a 16-week remote project.

In this role, you will use your real-world business knowledge to evaluate and compare responses from multiple AI chatbots across everyday small-business scenarios. You will create realistic business prompts, interact with AI tools, and provide structured feedback on the quality, accuracy, usefulness, and clarity of AI-generated responses.

This is an excellent opportunity for business owners, entrepreneurs, operators, and professionals with strong small-business experience who are comfortable working with AI tools and business documents.

Position Details

• Job Title: Small Business Owner – AI Evaluation Specialist
• Employment Type: Contractor Assignment
• Location: Remote – U.S. only
• Pay: $17/hour
• Schedule: Full-time, 40 hours per week
• Contract Length: 16 weeks
• Required Availability: At least 4 hours of PST overlap during the workday

We are looking for candidates who are:

• Current or former small business owners, entrepreneurs, or professionals with strong knowledge of small-business operations
• Native English speakers
• Located in one of the eligible U.S. states/territories listed below
• Able to commit to 40 hours per week for 16 weeks
• Strong in analytical and critical thinking
• Comfortable using AI chatbots and other digital tools
• Able to follow detailed evaluation guidelines consistently
• Comfortable working with PDFs, spreadsheets, images, business documents, and other files
• Able to provide realistic business scenarios based on their experience

Key Responsibilities

You will:

• Create realistic business-related prompts based on defined user goals
• Interact with multiple AI chatbots, with conversations of up to 5 turns
• Compare AI-generated responses across different models
• Evaluate responses for accuracy, clarity, usefulness, and relevance
• Provide structured feedback and comparative evaluations
• Submit conversation transcripts and evaluation results
• Use business documents, spreadsheets, PDFs, and images as part of your workflow
• Evaluate how effectively AI handles real-world small-business situations

Areas You May Evaluate

1. Marketing & Visual Content

Evaluate AI use cases involving:

• Business logos and product images
• Marketing campaigns
• Flyers and promotional materials
• Product catalogs
• Visual designs and artwork
• Creating or modifying business-related visual content

Important: At least 30% of conversations may require candidates to provide their own business logo, product images, or other relevant visual assets.

2. Daily Operations & Customer Management

Evaluate AI use cases involving:

• Daily business workflows
• Inventory and logistics
• Employee/team scheduling
• Customer interactions
• CRM-related tasks
• Administrative workflows
• Organizing business operations

Important: At least 50% of conversations may require candidates to provide file inputs, such as spreadsheets, PDFs, documents, or images.

3. Market Intelligence & Business Ideation

Evaluate AI responses related to:

• Competitor research
• Target audience analysis
• Ideal Customer Profiles (ICPs)
• Market opportunities and saturation
• Customer needs
• Marketing strategies
• SEO and growth ideas
• Launching, growing, or monetizing a business

4. Data Analysis & Financial Planning

Evaluate AI use cases involving:

• Business budgets
• Cash-flow tracking
• Bookkeeping workflows
• Pricing and quoting
• Profitability analysis
• Financial planning
• Business data analysis

Important: At least 80% of conversations in this area may require candidates to provide file inputs such as spreadsheets, PDFs, financial records, or other business documents.

Required Business Portfolio

Note: Candidates MUST have a business portfolio in English available for submission.

This is a remote position, but candidates must be physically located in one of the following U.S. locations:

• Alaska
• Arkansas
• Delaware
• Georgia
• Hawaii
• Illinois
• Indiana
• Kansas
• Louisiana
• Maine
• Maryland
• Nebraska
• Nevada
• New Hampshire
• New Mexico
• Ohio
• Oregon
• Puerto Rico
• Rhode Island
• Tennessee
• Utah
• Washington
• Washington, D.C.
• West Virginia

Candidates located outside the eligible locations will not be considered.

Why Join?

• 100% remote
• $17/hour
• Full-time, 40 hours/week
• 16-week contract
• Opportunity to work on real-world AI evaluation
• Use your existing business knowledge and experience
• Work with multiple AI technologies
• No specific industry background required

How to Apply

If you are a small business owner or have strong hands-on experience running or managing a small business, we encourage you to apply.

Please be prepared to submit your English-language business portfolio as part of the application process.

Candidates who meet the location, English-language, availability, and business-experience requirements will be contacted for the next steps.

Apply now!