In an age where organizations are racing to implement AI, few are asking the deeper questions: Are our systems ready? Are our people supported? Are we leading with soul?

In this powerful conversation, Dr. Reggie Padin sits down with Jessica Caresse, founder of J.Caresse & Company—a transformational consulting firm specializing in enterprise AI, cloud migration, and Project Management as a Service (PMaaS). As both a Microsoft and AWS Partner, her team bridges bold technology vision with seamless execution.

But Jessica’s impact goes far beyond frameworks and platforms.

As a systems thinker, strategist, and the voice behind the Connecting the Dots podcast, she brings a rare fusion of clarity, structure, and care—guiding organizations not only through technological shifts, but the human and cultural transformations required to make them stick.

Together, they explore:

• The evolving role of project managers in AI-powered transformation
• How to address the emotional undercurrents of change management
• Why organizations fail to operationalize strategy—and how to fix it
• The soul of systems design: building infrastructures that scale with depth
• What it means to lead with both precision and consciousness

Jessica’s mission is bold: to elevate humanity through technology and raise collective consciousness—one system, one strategy, one leader at a time.

Whether you’re an enterprise leader, L&D consultant, or AI advisor, this episode is a masterclass in what real transformation requires.

https://www.jcaresse.com/

www.ailcn.org