How I Built the "SDR Sidekick": Scaling AI Agents for Smarter Prospecting

​Joe is evolving the localized playbooks he previously shared into a broader, tech-enabled execution strategy. He has spent the last few weeks building and piloting what he calls a PG (Pipeline Generation) Sidekick. This is a localized Claude agent integrated directly into Slack and Gmail, built off of the consolidated "skills" and playbooks created by his top performers.

​Rather than letting reps build fragmented, random tools that waste hours of setup for minor efficiency, Joe’s approach consolidates these into a single enterprise-grade framework. Half of his team is currently piloting the agent to drive massive improvements in pipeline conversion while automating low-leverage research.

​This session will run as a "building in public" style experiment. Whether the pilot achieves massive scale or yields critical lessons from failure, Joe will pull back the curtain on what happens when a tech stack becomes truly AI-enabled.