Appointment Setter / Lead Outreach Specialist for AI & Web Agency (Trial, Long-Term Possible)

We're a small team building AI, automation, and web development solutions (voice agents, RAG systems, custom LLM workflows, dashboards, WordPress, Shopify, custom web apps). We're looking for someone to handle the first step of our sales process: finding the right people and getting them on a call with us. This post is a small paid trial. If it works for both sides, this turns into ongoing work with a real commission structure. What the trial looks like: - 100 outreach attempts to potential clients in the US, UK, or UAE - You research who to reach out to (small business owners, founders, marketing leads, ops leads who would benefit from AI, automation, or web work) - You send personalized pitches and follow up where it makes sense - The goal is not 100 sends. The goal is real conversations and ideally a booked call with us - 5 to 20 percent commission on any project that closes from leads you sourced. Commission scales with project size and is paid through Upwork on a separate milestone the moment we close a deal If the trial goes well: - We move to a monthly retainer plus commission - You get full briefing materials: who we are, our past work, case studies, pricing ranges, ideal client profile - You are not pitching alone, you are booking calls for us to take Who we are looking for: - Strong written English. The people you are messaging will be founders and operators in English-speaking markets, so the writing has to sound natural - Some understanding of what AI, automation, and web dev actually do, enough to write a pitch that does not sound clueless. You do not need to be a developer - Comfortable doing your own research to find good leads (LinkedIn, directories, communities, whatever works for you) - Honest about what worked and what did not. We would rather hear "20 sends, 2 replies, 0 booked" than inflated numbers Who this is not for: - Anyone planning to blast a generic template to 100 people. That hurts our brand and we will know - Pure list builders who do not write outreach - Anyone uncomfortable with a small trial budget. The real money here is the commission, and we are upfront about that To apply, answer these two questions in your proposal. We read every word, skip the templates: - Pick one of our services (voice agent, RAG, automation, custom dashboard, WordPress or Shopify, web app). Write the opening 3 lines of a cold message you would send to a US-based founder offering that service. Do not overthink it, just show us how you would actually write. - Where would you look first to find 100 qualified leads for this? Channel and rough approach is fine, you do not need a full plan. We will read proposals in the order they come in and reply to the ones that actually answer the questions. Looking forward to seeing what you send.