Outbound Sales Representative -- AI Automation Services We are an AI-native development shop delivering workflow automation and AI integration services to small and mid-sized businesses. The technical side is handled. We need someone who can find clients, run outreach, and close. This is a sales-focused role. You will be responsible for generating leads, running outbound campaigns, handling discovery calls, and converting prospects into paying clients -- primarily through Upwork and cold outreach. What you will do: - Identify and reach out to potential clients via Upwork, cold calls, and direct outreach - Write and send Upwork proposals and outreach messages - Run discovery calls and present our services clearly - Qualify leads and move prospects through the pipeline - Handle inbound inquiries and follow up consistently - Coordinate with the technical team to scope and price projects accurately Requirements: - Proven experience in outbound sales, cold calling, or business development - Comfortable running calls independently from intro to close - Strong written communication for proposals and outreach - Self-starter who manages a pipeline without hand-holding - Reliable setup for calls (stable connection, professional audio) Nice to have: - Experience selling tech, SaaS, digital services, or automation - Basic familiarity with AI tools or automation concepts - Active Upwork profile with proposal experience - Experience selling to SMBs Engagement details: - Long-term preferred - Commission-based or base + commission -- open to discussion depending on experience - Flexible hours, results-based When applying, please include: - A sales win you are proud of: industry, what you sold, how you closed it - Which outreach channel has worked best for you and why - Your preferred compensation structure and rate