How I Trained an AI Agent to Do My Cold Outreach

Cold outreach is broken, but what if you could train an AI agent to replicate your most effective, human-sounding emails? I sat down with Jim Weldon, CEO of Prospect Desk, whose team is building a "digital twin org chart" where human sales reps manage teams of specialized AI agents. He breaks down his exact process for How I Trained an AI Agent to Do My Cold Outreach, feeding it hundreds of his "founder prescribed" emails to avoid the generic, robotic messages that everyone hates. We also discuss how AI can automate 80% of an SDR's repetitive tasks and why we're still in the "stumble fumble" phase of AI adoption. This is an essential guide for any founder or sales leader looking to scale their prospecting without losing the human touch. Check out the company: https://prospectdesk.ai

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🕒 CHAPTERS

00:00 - Introduction: The End of Cold Outreach As We Know It

00:45 - Why You Need to Automate 80% of Sales Tasks

02:00 - The "Digital Twin Org Chart": Your SDR's New AI Team

03:20 - The Future of AI Interaction is Voice, Not Slack

05:20 - How an AI Manager Coordinates The Playbook

07:25 - Can a Solopreneur Build Their Own AI Sales Team?

09:50 - How Our AI Agents Work Across Different Channels

14:05 - The #1 Challenge: Making AI an Expert Strategist

17:00 - Why AI Voice Agents Still Struggle with Outbound Calls

20:25 - My Process for Training an AI to Write "Founder Prescribed" Emails

22:20 - The Surprising Power of a LinkedIn Voice Message

28:20 - The "Stumble Fumble" Hype Cycle of AI

30:20 - The Greatest Technological Change Ever

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