What does it take to build companies that last in the age of AI?

In this episode of AI: Voice or Victim, hosts Erica Rooney and Greg Boone sit down with Jesse Lipson, founder of ShareFile and now CEO of Levitate, a marketing software helping over 7,000 small businesses strengthen client relationships with AI.

Jesse shares lessons from launching ShareFile at the dawn of the cloud era, why competing for attention is the new battleground in software, and how Levitate uses AI to keep outreach personal and authentic—without falling into the trap of automation overload.

We dive into:

How small businesses can adopt AI responsibly without getting overwhelmed.

Why documenting your processes is the hidden key to AI readiness.

The human skills that matter most in an AI-driven future.

Jesse’s personal philosophy on innovation, taste, and building technology that truly empowers people.

Whether you’re running a small business, leading a team, or just trying to stay competitive, Jesse’s perspective will help you reimagine how AI can support—not replace—the human connections that drive growth.

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