In this episode, I interview Chelsy Bell Carpenter, a leadership strategist whose work sits at the intersection of high performance and humanity. Chelsy’s journey into insurance started in marketing, but quickly evolved as she became deeply connected to the human side of claims and the real impact of loss on people’s lives. From there, she stepped into claims adjusting and even helped build out claims operations at an Insurtech startup, gaining a full view of the industry along the way. Chelsy's experiences ultimately led her to question what success actually looks like.

We spent a lot of time talking about burnout, not just as a buzzword, but as something very real that many professionals navigate. Chelsy shared her own experience of running on autopilot and how it forced her to completely shift from constant output to sustainable, intentional performance. What I appreciated most was her honesty and her mission to normalize these conversations, especially for women who often carry the weight of being both high achievers and caretakers. Through her “Built to Last” program, she’s helping leaders build resilience in a way that’s actually realistic through simple, repeatable practices that support both well-being and performance.

In this episode, I interview Kim Cathey, Release Manager at RGA, whose career journey is anything but linear, and exactly the kind of story that reminds me there’s no one “right” path into this industry. From a high school internship at a State Farm agent’s office to roles across fashion, banking, aerospace, and ultimately insurance, Kim has built her career through curiosity, adaptability, and connection. What made this conversation especially meaningful for me was hearing how a simple LinkedIn post, one connected to this very podcast, led Kim to an introduction to Sandy Hubert. It was such a full-circle moment and a reminder of how powerful visibility and community can be in shaping someone’s path.

We spent a lot of time talking about what leadership really looks like in practice, and Kim shared something that stuck with me: kindness and niceness are not the same thing. She leads with genuine care for her team, while still having the hard conversations and driving meaningful change. We talked about how she approaches leadership through what she calls the four C’s: collaboration, communication, coordination, and consideration, and how that balance is critical when guiding teams through change. Kim is grounded in authenticity, being honest when she doesn’t have all the answers, creating space for others to speak up, and leading in a way that makes people feel both supported and challenged.

In this episode, I interview Alexis Simmons, a Senior Builder’s Risk Underwriter at Axis Capital. Over the past decade, Alexis has built her career across organizations such as Liberty Mutual and The Hartford, and today she leads with both technical expertise and heart, managing her book of business and partnering closely with brokers. But what I’ve always admired most about Alexis is how she shows up. From her leadership in industry initiatives like Dive In to her commitment to advocacy and inclusion, she brings intention and authenticity into every space she’s part of.

Our conversation went beyond career milestones and into the realities behind them. Alexis opened up about her experience as a Black woman and a single working mother in this industry, the challenges, the growth, and the importance of creating environments where people feel psychologically safe and truly seen. We talked about the responsibility we all have to advocate for more equitable practices, from supporting neurodivergent colleagues to rethinking policies that impact working parents. What stayed with me most was her advice to trust yourself, listen to your intuition, and lead as your full, authentic self.