In this episode, I interview Stephanie Dewald, Executive Vice President and Zonal Distribution Leader for Major Accounts at Chubb, who brings over three decades of exceptional industry experience. Stephanie shares her unexpected journey into insurance after starting out as a computer science nerd, and how those early tech roots continue to fuel her adaptability and curiosity today. We also dive deep into her powerhouse background as a Division I tennis alumna and endurance athlete, exploring how the discipline, structure, and lessons learned from handling defeat gracefully have shaped her professional resilience.

Beyond her athletic and career milestones, Stephanie offers powerful insights into modern leadership, discussing how she fosters a safe, collaborative environment for her team by treating mistakes as solvable learning opportunities rather than reasons for fear. We also examine the evolution of female leadership since the 1990s, the importance of embracing authentic strengths, and what it truly takes to drive sustainable, top-down equity and inclusion in the insurance industry so that leadership genuinely reflects a diverse customer base.

In this episode, I interview Angela Ripley, President of VW Brown Insurance Service and national chairperson of the Big I, who shares her journey growing up around an insurance agency and later rising to lead a 130-year-old organization. Angela shares the evolution of leadership styles, the power of mentorship, and why she believes in focusing on true talent and skill development across the board rather than siloing demographic groups.

Angela also shares the special connections she has made with female agency owners across the country in states like Alaska, Montana, and Maine. We also explore exciting industry topics, from breaking away from gimmicky insurance advertising to attract the next generation of professionals to the positive impact of technology and AI on our daily work.

In this episode, in partnership with the National African American Insurance Association (NAAIA), I interview Susan Johnson, Chief Culture Officer at The Hartford and Vice Chair of NAAIA's Board of Directors, for a deeply insightful conversation about what it truly means to build sustainable, value-driven inclusion within the insurance industry. Susan shares her unique journey into insurance from outside the traditional mold, offering a refreshing perspective on why we need to look beyond the same talent sources, rethink job descriptions, and tell a much broader, more compelling story about the diverse career paths available in our industry.

Susan also shares how organizations can move past surface-level checklists and embed cultural belonging directly into everyday business operations, leadership behaviors, and talent systems. Susan provides incredible wisdom on navigating organizational transformation without putting culture on hold, fostering non-judgmental curiosity among all employees, and how executives can leverage strategic partnerships with organizations like NAAIA to drive real business and talent results.

In this episode, I interview Rajni Kapur, CEO of one of California’s largest independently owned insurance agencies, All Solutions Insurance. We discuss her inspiring path from CPA to insurance leader. Rajni opens up about the resilience required to launch her agency in 2003 while navigating the complexities of new motherhood, explaining how those early years shaped her leadership philosophy. She shares her powerful perspective on why working mothers don't need reduced responsibilities, but rather the trust and flexibility to excel while managing their family lives.

The conversation also dives deep into Rajni’s commitment to building a workplace culture that normalizes real-life challenges, including her policy of welcoming children into the office when needed. Rajni also emphasizes the "clear but kind" feedback approach and the need for intentional support systems that foster growth rather than discourage. Rajni also details her ambitious vision for the future, including her plans to create educational programs and measurable pathways to help more women secure equitable leadership roles within the insurance industry.

In this episode, I interview Candace Steele, Group Risk Director at Canopius Group Limited, for a conversation that spans continents and decades of resilience. Candace shares the fascinating story of how a manager’s recommendation to move to Bermuda during Hurricane Ivan accidentally launched her into the insurance industry. This path that eventually took her from her professional foundations in Canada to building a life and career in Bermuda and, most recently, the UK. We dive into what it truly means to navigate international moves with small children, the importance of maintaining your core values while adapting to new cultures, and why building a network is more critical than ever in an era where AI is changing how we approach hiring.

Candace also offers a refreshing perspective on the delicate balance between hard work and professional visibility. We unpack why women shouldn't wait to be noticed, but rather advocate for themselves with intention, and how external coaching can be a game-changer for building confidence early in one's career. From the necessity of genuine human connection in our global industry to the power of taking professional leaps before you feel "perfectly ready," Candace’s insights on sponsorship, mentorship, and self-advocacy are incredibly empowering.

In this episode, I interview Jennifer Kapp, Partner at Cruser, Mitchell, Novitz, Sanchez, Gaston & Zimet, LLP, to talk about her unique journey into the insurance industry, the realities of working motherhood, and why flexibility is the ultimate key to retaining top talent. Jennifer shares how she originally graduated from law school in 2008 during the economic downturn with the intention of pursuing public interest work, only to find herself stepping into the insurance world through a family connection. From there, she built a thriving career spanning claims, complex litigation, and thought leadership, proving that career paths do not need to follow a rigid, linear trajectory.

We discuss the challenges of navigating corporate return-to-office mandates, the power of authentic social media connections, and how her firm fosters an equitable environment by prioritizing autonomy and remote work. Jennifer also opens up about the beautiful mess of balancing a demanding legal career with raising three children, sharing why she believes women shouldn't feel pressured to do it all perfectly.

In this episode, I interview Layla Farivar, Employee Benefits Consultant at IMA Financial Group. Layla shares her inspiring career journey from the mortgage industry to finding her true passion in employee benefits. Layla opens up about transitioning from marketing to sales, sharing her refreshing perspective on why true confidence is built over time and how supportive leaders and powerful brand representation paved the way for her success.

Layla also talks about redefining modern leadership, and candidly explains why she chose to step away from people management to focus on individual contributions, and why it is vital to normalize that leadership doesn't always mean managing a team. Layla also shares her advice for women entering male-dominated spaces, the impact of IMA's women's network, and her take on what it takes to create a more equitable playing field in insurance.

In this episode, I interview Shanna Sweeney, SVP of Excess Casualty at Upland Specialty Insurance and co-founder of Women of Wholesale (WOW). Shanna shares how an unexpected start in insurance through an Enterprise Rent-A-Car internship led to a 15-year career in reinsurance, proving that you don’t need a traditional risk management degree to find your place and thrive in this space.

We also talk about the power of community building and why Shanna created WOW to give women a safe, non-judgmental space to build authentic relationships before they need them. Shanna offers refreshing, practical insights on moving past workplace competition with an abundance mindset, the importance of sponsorship over mere mentorship, and how designing for diversity can genuinely reshape the C-suite. Plus, she shares why her favorite part of the industry has been the lifelong friendships forged along the way.