In this episode of Prospecting Pros, John and Chris chat with Jason Bay, founder of Outbound Squad. Jason breaks down how he helps sales teams turn everyday call data into insights that actually drive revenue. He explains how the best messaging doesn’t come from guesswork, but from real customer conversations, and why teams should treat call recordings like a goldmine for training and enablement.
Jason also talks about the growing role of AI in sales and where it can genuinely make an impact. He shares how tools that enrich data, summarize calls, and make coaching easier are game changers, while full “AI SDR” replacements still have a long way to go. The group also digs into what’s working in outbound today, from tighter ICPs and stronger offers to smaller, more personal in-person events that drive trust and connection.
