You know when two different people tell you, “You really need to meet her”? There’s usually a reason.
That was Jess Caire for me. And they were right.

Jess is sharp, accomplished, and leads in a space that’s traditionally male and corporate. But what struck me wasn’t just what she does. It was how she does it. She’s warm, funny, self-aware, and disarmingly real. The kind of person who makes you feel at ease while also reminding you of what’s possible.

In this episode, Jess shares her journey, from running her own business at 25, to stepping into senior leadership roles and navigating rooms not always designed for women. She’s honest about the learning, generous with her insight, and never afraid to laugh at herself.

Jess is a reminder that the best leaders aren’t the ones who pretend they’ve arrived. They’re the ones who stay open, keep growing, and lead with both impact and humility.