AI SDR Books $200K/Month in Sales Calls with Tom Crawshaw

In this episode of This New Way, Aydin sits down with Tom Crawshaw, founder of an AI automation agency, to explore how he built an AI SDR (Sales Development Rep) system that books over $200,000 in sales calls per month—completely automated and with no humans in the loop. Tom breaks down the tech stack, the flow of conversations, and why these two-way AI-powered chats sound so natural that they’re almost undetectable as bots. He also shares how this system scales personalized customer conversations at a fraction of the cost, and how similar workflows can be applied to everything from e-commerce abandoned carts to B2B demo follow-ups. Timestamps: 1:15 – Tom’s background and pivot from email/SMS marketing to AI automation 2:57 – Why AI enables true two-way conversations at scale 4:06 – Building custom AI SDR agents vs. off-the-shelf chatbots 6:09 – Live demo: Booking a sales call through the AI SDR workflow 10:13 – How the system qualifies leads and handles objections 12:04 – Tech stack breakdown: Go High Level, N8N, Twilio, and A2P verification 17:02 – Under the hood: prompts, custom fields, and conversation logic 23:00 – Automating what 1,000 SDRs would do manually 27:04 – Costs: Running conversations at $0.25 each 29:25 – Other use cases: abandoned carts, B2B no-show follow-ups, e-commerce 34:00 – Context files: training AI on viral posts and high-performing copy 38:14 – Prompt Cowboy: turning lazy prompts into viral-ready content 40:29 – Where to follow Tom and learn more about AI SDR systems Tools & Technologies Mentioned: Go High Level – CRM platform used for SMS automation and pipeline management N8N – Workflow automation tool connecting AI agents and custom scripts Twilio – SMS and WhatsApp messaging infrastructure A2P Verification – Compliance process required for sending business SMS in the US and Canada OpenAI / Claude – LLMs powering natural language conversations Prompt Cowboy – Tool for turning simple prompts into fully structured, optimized ones for better AI output Subscribe at⁠ thisnewway.com⁠ to get the step-by-step playbooks, tools, and workflows.