Business Development / B2B Sales - sell custom Python & AI development (full-cycle, long-term)

Individual freelancers only. No agencies, no sub-contracting. Flexipy is a small Python and AI development agency. The founder is a senior engineer who still writes code and joins every technical call. We build production AI systems — agents, RAG, LLM integrations — and the Django/FastAPI backends underneath them. On Upwork: 100% Job Success, Top Rated, 18 contracts, all 5.0. You would be our first salesperson. There is no machine to step into — there are ICPs, a CRM, proposal templates and one proven channel, but the outbound playbook is early and you would help write it. If you want a funnel that feeds you qualified leads, you would be unhappy here. THE ROLE — FULL CYCLE You find the clients, you open them, you grow them. There is no lead-gen team; prospecting is the job, not something handed to you. • Build and qualify prospect lists on Upwork, LinkedIn and direct outreach • Qualify on expansion potential, not deal size — a small first project with a company that can grow beats a bigger one that can't • Write outreach and follow-ups that don't read like templates • Book first conversations and run the commercial side; the founder runs technical scoping • Run the expansion conversation after a client's first project ships. This is the part that matters most • Turn call recordings into scope documents, SOWs and an open-questions list — you write it up, the founder does the technical elicitation • Keep the CRM honest, help refresh ICPs and case studies MUST HAVE • You have sold custom development, outsourcing or consulting — SERVICES, NOT PRODUCTS. Selling a known product with a brand behind it is a different job and doesn't transfer. Point us at the evidence: which companies, which clients, your Upwork history • Hands-on outreach experience on Upwork and/or LinkedIn • Written English good enough for client-facing proposals (B2+/C1 minimum) • AI tools in your daily work — Claude, ChatGPT, agents — for research, drafting, proposals, CRM updates and follow-ups. This is a requirement, not a bonus • Comfortable being the only salesperson, reporting directly to the founder • Self-organised, detail-oriented, honest about what isn't working NICE TO HAVE • Experience at a software development agency • Pipedrive, HubSpot or similar • Apollo, Instantly, Smartlead, Sales Navigator, Hunter • Enough AI and LLM understanding to hold a first conversation credibly TERMS • Hourly, with the Upwork tracker on • 25 hours a week to start, capped. We would rather buy focused hours than seat time, and the cap goes up when the pipeline justifies it • Flexible hours, 4+ hours of overlap with EET • Long-term, contract-to-hire. If this works it becomes a full-time role — and commission starts at week 9 either way MONEY Hourly rate depending on experience. Straight hourly for the first 8 weeks — no quota, no target to clear, no part of your pay at risk while we're both still learning what this channel does. From week 9 you also earn 4% of every invoice a client you own actually pays us, on top of the hourly rate. Not a replacement for it. • Paid on money received, not signed value, so nothing waits on a milestone that moved • Sent monthly through Upwork as a bonus, grossed up so that 4% is what you keep after Upwork's fee • No cap, no threshold. It pays from that client's first payment • It keeps paying as long as that client keeps buying — not only on their first project • It survives the move to a direct contract if we convert you We won't quote you a monthly figure, because that depends entirely on what you build. What we will do is keep the mechanism transparent: a percentage of invoices you can check yourself, every month, against the same numbers we see. HOW WE HIRE 1. A 30-minute call — mutual fit 2. A two-week paid trial at the full rate, 25 hours a week. Real ICPs, real outreach, goals agreed in writing on day one: prospects researched, sequences built, outreach sent, CRM kept honest. If it isn't working for either of us we stop there, and you've been paid for every hour 3. Continue. Weeks 3–8 add replies and calls booked. Closed deals are not an early metric — our sales cycle is longer than that We're a small company building this function for the first time. Month one sets our baseline as much as it measures you, and we'd rather agree real numbers with you than invent them now. TO APPLY Answer the screening questions. Short and specific beats long and polished. A template proposal is an automatic no — we can tell. WHAT WE VALUE Honesty, including when something isn't working. Ownership. Attention to detail. Long-term cooperation. If a budget or timeline doesn't match reality we say so early, internally and with clients. We'd expect the same from you.