The AI Operator Podcast: Why Outbound Tools Break Your CRM

Most sales teams don’t realize how messy their CRM is—until it’s too late. In this episode of The AI Operator, Jordan interviews OutboundSync founder Harris Kenny to talk about the hidden cost of bad integrations and disconnected outbound tools.

From his early days running a fractional sales agency to building a product that bridges Smartlead, HubSpot, and Salesforce, Harris shares what he’s learned about fixing data chaos, scaling outbound the right way, and avoiding the trend-chasing trap.

If your CRM is a black box or your workflows feel like duct tape, you’ll want to listen.

Listen