Why Relationship-First Platforms Will Win The Next AI Wave

 

Why do small business leaders keep buying more software yet still feel like they are drowning in logins, dashboards, and unfinished work?

In this episode of Tech Talks Daily, I sit down with Jesse Lipson, founder and CEO of Levitate, to unpack a frustration I hear from business owners almost daily. After years of being pitched yet another tool, many leaders now spend hours each week troubleshooting software instead of serving customers. Jesse brings a grounded perspective shaped by decades of building SaaS companies, including bootstrapping ShareFile before its acquisition by Citrix, and what stood out to me immediately was how clearly he articulates where the current software model has broken down for small businesses.

We talk about why adding more apps has not translated into better outcomes, especially for teams without dedicated specialists in marketing, finance, or sales. Jesse explains how traditional software often solves only part of the problem, leaving owners to become accidental experts in accounting, marketing strategy, or customer communications just to make the tools usable. From there, our conversation shifts toward what he believes will actually matter as AI adoption matures. Rather than chasing full automation or shiny new dashboards, Jesse argues that the real opportunity lies in blending intelligence with human guidance, allowing AI to work quietly behind the scenes while people remain the face of authentic relationships.

A big part of our discussion centers on trust and connection in an AI-saturated world. Jesse shares why customers have become incredibly good at spotting automated communication and why relationship-based businesses cannot afford to lose the human element. We ex