SMB AI Power User – Competitive Evaluations (Remote Contractor)

About the role

We are looking for an experienced SMB AI Power User to conduct competitive evaluations of generative AI assistants in real‑world small‑business scenarios. You will run head‑to‑head tests, document performance gaps, and produce reproducible reports that help shape product strategy.

Key responsibilities

• Design and execute multi‑turn workflows that mimic everyday SMB tasks such as advertising copy creation, content planning, customer communication, pricing analysis, scheduling, and bookkeeping.
• Maintain a curated library of practical test cases covering social media, commerce platforms, and conversational interfaces.
• Identify and document failure modes including inaccurate answers, refusals, tone issues, unsafe content, formatting errors, loss of context, and unusable media outputs.
• Produce clear evaluation reports detailing prompts, AI model used, expected vs. actual results, severity, and business impact.
• Compare bundled AI subscription value against competing paid assistants based on realistic use cases and cost.

Required profile

• Current or recent experience as owner, founder, sole proprietor, or day‑to‑day operator of a small‑ or medium‑size business (1‑200 employees).
• Daily, habitual use of generative AI tools for business operations and marketing.
• Hands‑on management of Instagram and Facebook business pages, including posts, stories, reels, and customer messages.
• Experience creating and optimizing paid advertising campaigns on Meta platforms with real budgets.
• Based in the United States and authorized to work there.
• Exceptional written English and strong analytical skills.

Required skills

• Canva
• AI automations
• Klaviyo
• Meta paid advertising
• QuickBooks
• Generative AI tools (ChatGPT Plus, Claude Pro, Gemini Advanced, etc.)
• AI assistants and custom GPTs
• No‑code integrations and APIs
• Model evaluation, red teaming, data annotation, quality assurance
• Shopify, Square, CapCut, Later

What we offer

• Contractor compensation of $40–$50 per hour, based on experience and location.
• Fully remote work with flexible weekly hours up to 40 h.
• Direct exposure to cutting‑edge generative AI products and competitive assistants.
• Opportunity to influence how AI tools serve real small‑business users.