In this episode, I interview Kateryna Monastyrska, Head of Sales and Marketing at DICEUS, for a candid conversation on modernizing insurance technology and leading with purpose. Kateryna shares how a custom software project first drew her into the industry, highlighting the striking contrast between the complex, high-stakes decisions insurers make every day and the outdated, spreadsheet-heavy systems supporting them. We dive into how alternative risk organizations, captive managers, and RRGs can move away from legacy processes to achieve real efficiency, and why successful AI adoption must always start with solving a clear business problem rather than just chasing tech trends.

Beyond digital transformation, Kateryna reflects on the uniquely open and supportive community of women in insurance, sharing how high-level mentorship from female C-suite leaders helped shape her own career trajectory. She opens up about the realities of balancing an ambitious insurtech career with motherhood across time zones, the power of leading through trust and results over optics, and her vision for building true equity, from sponsoring women into key roles to attracting top talent earlier into our industry.

In this episode, I interview Natalie Golubski, Professional Lines Broker at Jencap Group. Natalie shared how she initially found insurance through a family connection at Russell Bond and why she's stayed: the incredible people, the deep-rooted Buffalo insurance community, and an office culture where colleagues truly feel like family. We dive into how mastering operational foundations built the strong base she relies on as a producer today, and why she believes bringing your 100% authentic self to work beats wearing a corporate mask every single time.

Natalie also shares her deep commitment to giving back, from her leadership roles across local insurance organizations like the Insurance Women of Buffalo to her viral "Bald for Bucks" challenge where she raised over $6,300 for the Roswell Park Cancer Institute and donated her hair to support children facing hair loss. Natalie also shares her vision for a more equitable playing field in our industry by introducing diverse, lower-income students to insurance careers early on.

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.