SMB AI Power User — Competitive Evaluations

As an SMB AI Power User, you’ll help evaluate how AI assistants perform against the real-world needs of small and medium-sized businesses. You’ll use your own business experience and daily workflows as a practical testing environment, comparing competing AI tools side by side. Your work will cover marketing, customer communication, research, pricing, scheduling, content creation, and other everyday business tasks. You’ll identify where AI assistants succeed, where they fall short, and which limitations could affect paying business users. The role combines hands-on business operations, structured testing, and detailed technical reporting. It’s an independent, output-focused opportunity for someone who already relies heavily on generative AI in their professional life.

• Current or recent experience as the owner, founder, sole proprietor, or day-to-day operator of a small or medium-sized business, ideally with approximately 1–200 employees.
• Daily, habitual use of generative AI tools for both business operations and marketing; occasional or experimental AI use is not sufficient.
• Hands-on management of a business presence on Instagram and Facebook, including posts, Stories, Reels, comments, and customer messages.
• Practical experience creating, launching, and optimizing paid advertising campaigns on Meta platforms using real advertising budgets.
• Based in the United States and authorized to work there, according to the original role requirements.
• Availability to complete the agreed deliverables and workload, potentially up to 40 hours per week.
• Exceptional written English, with the ability to explain AI failures clearly and precisely enough for an engineer to reproduce them without additional clarification.
• Strong analytical and observational skills, with an ability to distinguish meaningful product limitations from minor inconsistencies.
• Comfortable working independently, following structured evaluation criteria, documenting findings, and consistently meeting weekly output expectations.
• Experience with paid AI subscriptions such as ChatGPT Plus/Pro, Claude Pro/Max, Gemini Advanced, or similar is a plus.
• Experience using multiple AI assistants simultaneously and comparing their practical strengths and limitations is advantageous.
• Familiarity with AI automations, agents, APIs, no-code integrations, custom GPTs, or similar tools is a plus.
• Previous experience in model evaluation, red teaming, data annotation, quality assurance, or structured user research is beneficial.
• Familiarity with SMB tools such as Shopify, Square, QuickBooks, Klaviyo, Canva, CapCut, or Later is an advantage.