This special episode was recorded live in New York City as the opening to Women at the Top: Reaching the Apex in Work and Life, presented by Tyson & Mendes’ Women’s Initiative. In collaboration with InsHER, National Managing Partner Cayce Lynch and Partner, Head of Growth & Client Engagement Ashley Fetyko (both of Tyson & Mendes), and hosts of The Normal Mess, graciously invited me to help kick off the event with a dynamic, live conversation.

Together, we explored what it really means to find your voice, take up space, and uplift others along the way. It set the tone for an incredible day, one grounded in honesty, connection, and the power of women showing up fully, both in work and in life.

In this episode, I had the chance to do something a little different, and really special, by hosting my first-ever mother-son conversation with Legia and Lukas Oswald. Legia, founder and CEO of Out of Pocket EXP, has spent years in the insurance and temporary housing space, and together with her son Lukas, they’ve built a business focused on improving how additional living expense claims are handled. Hearing how Legia was introduced to the industry and ultimately co-founded a company with her son was such a full-circle story rooted in real frustrations, real experiences, and a genuine desire to make things better for adjusters and the families they serve.

What I loved most about this conversation was the mutual respect for one another’s strengths. Legia brings deep industry experience and a strong customer-first mindset, while Lukas adds a fresh perspective shaped by technology, product thinking, and a younger voice in the industry. Together, they challenge each other, learn from each other, and lead in a way that’s grounded in trust, respect, and open communication. We talked about what it’s like to build a business as a family, the leadership lessons they’ve learned along the way, and why the future of insurance depends on bringing together experience and new perspectives.

In this episode, I interview Maria Trapenasso, SVP and National Practice Leader of Talent Solutions at NFP, whose career journey brings such a unique and important perspective to our industry. Maria started in HR before transitioning into insurance sales, even earning her health and life license so she could work directly with individuals. Her dual lens, understanding both employee needs and business priorities, really shapes how she shows up today. What stood out to me right away is how deeply she understands the gap that can exist between what companies think employees need and what they’re actually experiencing in real life.

Our conversation focused on menopause in the workplace. Maria shared eye-opening insights on how this natural life stage is impacting productivity, retention, and, importantly, some of the most experienced women in the workforce. We talked about how often organizations overlook this entirely, despite the very real business implications, and why it’s time to approach it not just as a personal issue, but as a workforce strategy. I appreciated how practical Maria was, from creating safe spaces for employees to have a voice, to educating managers, to building policies that actually reflect the realities of a multi-generational workforce.

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.

In this episode, I interview three incredible women: Yolanda Austin, Katie Hughes, and Candace Duncan. Each of them has built a unique path in insurance, from claims to data and AI governance to industry standards, but the common thread is community. We talked about our involvement in the Women in Insurance Initiative and how it’s created a space where women can connect across roles, companies, and experiences, not just to network, but to truly support one another.

There are honest moments around confidence, mentorship, and growth. We talked about the pressure to be perfect, the tendency to put others first, and how mentorship, community, and even small moments of encouragement can change the trajectory of a career. We also explored what the future of our industry requires, not just technical skills, but empathy, communication, and ethical thinking.

To get involved with the Women in Insurance Initiative, visit: https://womenininsurance.stemconnector.com/home

In this episode, I interview Sharné Liebenberg, founder of Unrisked, a boutique risk consultancy based in Johannesburg, whose path into insurance is anything but traditional. With a background in journalism, Sharné brings a unique lens to underwriting, one rooted in curiosity, empathy, and a deep commitment to understanding people before assessing their risk. We talked about how that perspective has shaped her work in the trucking and logistics space, where she focuses not just on data points, but on the human decisions behind the wheel.

Sharné also shared how the loss of her brother reshaped her outlook on life and work, pushing her to prioritize meaning, autonomy, and intentionality. That shift has influenced everything from how she shows up for clients to her recent work in building AI-driven safety tools designed to support, not replace, human decision-making. What stood out most to me is Sharné’s belief that insurance is, at its core, about people, and that we have a responsibility to reflect that in how we assess risk, build technology, and serve our clients.