In the season 1 finale, I sit down with Shannon Alfonso, recently retired insurance executive who led Marsh McLennan Agency’s Florida Region to remarkable success during her nearly 30-year career. From an unplanned start in underwriting to becoming the region’s first female CEO, Shannon’s story is one of curiosity, courage, and staying true to her core beliefs. She shares how a willingness to learn, embrace new challenges, and build strong teams shaped her journey. Shannon reflects on overcoming imposter syndrome, trusting her instincts, and the pivotal moments that defined her career. Her advice for aspiring leaders? “You very well can be the right fit. You just have to embrace it. Be confident. Go for it.”

Now retired at 54, Shannon reveals why she chose to step away from the corporate world while at the peak of her career, challenging the traditional norms of retirement. She speaks candidly about the sacrifices she made for her career and how those shaped her decision to prioritize time with her family. Shannon shares how she's embracing the next chapter with rest, reflection, and the freedom to pursue meaningful work on her own terms.

In this episode, I’m joined by Janice Kowell, Managing Director and U.S. & Canadian Marine Cargo and Logistics Leader at Marsh, whose remarkable 30-year career is full of inspiring lessons and the power of self-advocacy. Janice shares how insurance “found her” fresh out of college, starting in a clerical role but quickly recognizing opportunities to make a meaningful impact. With the support of her mentor, she embraced challenges, introduced efficiencies, and moved into management within just three years. From being a young woman navigating the corporate landscape in Texas to taking courageous steps that defied age and gender expectations, Janice proves that knowledge is the foundation of confidence—and confidence can conquer any barrier.

Throughout her career, Janice learned the importance of belonging, mentorship, and advocating for oneself. She reflects on her bold move to the Pacific Northwest, where she rediscovered community, and built new connections. Now a mentor herself, Janice shares her approach to empowering others, encouraging them to set goals, take risks, and champion their own growth. She offers advice for overcoming self-doubt by imagining the advocacy we’d show for someone we love. As she reflects on her career, Janice wishes she had taken more risks sooner, a powerful reminder to all of us to be brave, clear in our ambitions, and unafraid to ask for what we deserve.

In this episode of InsHER, I interview Vanessa Sims, the Director of Diversity, Equity & Inclusion at the WSIA Diversity Foundation. With a background in financial services, Vanessa shares her journey of being called to a role where she could make a deeper, more meaningful impact. We discuss how the WSIA Diversity Foundation focuses on attracting diverse talent, fostering inclusive workplaces, and reimagining association governance to create sustainable change in the insurance industry. Vanessa emphasizes the importance of embracing diverse lived experiences, particularly in the E&S segment, which thrives on innovation and relationships. By intentionally seeking talent outside traditional risk management paths, WSIA is broadening the pool of future insurance leaders.

Vanessa also highlights the power of collaboration with industry organizations like NAAIA, LAIA, and NAIC, advocating for a “better together” approach to DEI initiatives. She shares her wisdom on “working with the willing,” focusing energy on promoters rather than convincing skeptics, and explains why ignoring diversity poses significant risks to the future of the industry. For those passionate about making a difference in environments where DEI doesn’t seem a priority, Vanessa offers heartfelt advice: "Follow your heart. Follow your heart and your values. Your heart will lead you to the right thing to do within your area of influence.”