Advertise on podcast: InsHER

This special episode was recorded from a webinar in partnership with the Women In Insurance Collective (WIIC). Drawing from over 100 candid interviews across the industry, this webinar moves past corporate buzzwords to share the collective wisdom and lived experiences of women in insurance. InsHER host and WIIC Communications & Awareness Committee co-lead, Megan Bell, asks every guest a single, powerful question: “If you had a seat in the C-suite, what would you do to create a more equitable playing field?” This session unpacks the patterns found in those answers, revealing that for many leaders, true equity is an ongoing balancing act rather than a checkbox exercise. Join us for a human-centered discussion exploring the ideas, suggestions, and realities shared by the InsHER guests. We’ll examine operational friction, long-standing industry norms, and ideas of how to approach sustainable progress while maintaining organizational balance.

In this second episode, in partnership with the National African American Insurance Association (NAAIA), I interview Rebekah Ratliff, International Mediator and Arbitrator at JAMS. Rebekah is a servant leader and long-standing NAAIA advocate. Rebekah shares her remarkable 35-year journey, from earning a psychology degree to becoming a commercial claims professional and global dispute resolver. Throughout our conversation, she reflects on how staying curious, leading with faith, and leaning into continuous learning have shaped her career, while offering invaluable insights on the critical difference between workplace authenticity and assimilation. Rebekah also details her passion for uplifting the next generation of diverse insurance professionals. She highlights the powerful impact of trade associations like NAAIA. She shares her visionary work with HBCU Impact, including her insurance course at Howard University School of Law, the Global Impact initiative taking students to London, and expanding cross-border connections in Africa. Rebekah champions focused mentorship and career development as the true keys to securing a vibrant, inclusive future for the industry.

In this episode, I was thrilled to interview industry leaders Sabrina Hart, President and Chief Executive Officer of Munich Re Specialty Insurance North America, Christina Colby, Chief Customer Officer at Guidewire, and Rita Jupe, Founder of The Jupe Group, for an engaging discussion in partnership with the ISC Group. The group explored the remarkable two-decade evolution of ISC Group, reflecting on how this global community has grown from early gatherings into a powerful development program that actively shapes leadership pipelines and drives inclusive cultures. The three leaders discussed the unique community spirit of the insurance industry, which is rooted in a shared mission to protect society, and emphasized why diversity and inclusion must be treated as strategic business enablers rather than mere HR checkboxes. The conversation also looked ahead to the future, examining how emerging technologies like AI can serve as a workplace equalizer by streamlining routine tasks and creating more flexible ways of working. The group closed with valuable insights for C-suite leaders on fostering equitable playing fields through intentional succession planning, spotting non-obvious talent, and modeling active sponsorship and mentorship.

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 Mary O’Leary Dronson, Managing Director, Corporate Segment Team Leader, and Senior Account Executive at Marsh, to explore her inspiring journey from starting as an accounting clerk with tuition reimbursement to leading corporate segments. Mary shares how growing up as the middle child taught her to continually advocate for herself and adopt the powerful mindset of "why not me?" when pursuing career growth. We unpack the systemic barriers and societal conditioning, from traditional media tropes to passive expectations, that often hold women back from speaking up or stepping forward for major professional opportunities. Balanced with humor, Mary also recounts memorable career milestones, including completing her degree at Temple University in just 18 months while working full-time and turning a nerve-wracking interview moment featuring a severe cold sore into an ice-breaking triumph. Mary emphasizes the vital roles that authenticity, mentorship, and proactive sponsorship play in reshaping the insurance industry.

In this episode, in collaboration with ISC Group, I interview Margaret Resce Milkint, Managing Director and Global Insurance Practice Leader at DSG Global and U.S. Chair of ISC Group. We share an insightful conversation on leadership, community, and industry evolution. We explore the transformative growth of the ISC Group as a vital "sanctuary" that fosters deep personal and professional connections for women in insurance. Margaret shares powerful perspectives on the power of mutual support, breaking traditional molds, and the shifting dynamics of female leadership where women actively lift and amplify one another. Margaret also dives into the future of work, examining how women can leverage artificial intelligence as a strategic coach to enhance executive communication, bridge technological gaps, and shape industry standards. Margaret offers actionable advice on building personal gravitas, establishing a diverse personal advisory board, and redefining success on one's own terms.

In this episode, I interview Danielle Clifford, Vice President and Head of Sales and Marketing at Openly, for an insightful conversation on career paths, sales leadership, and finding authentic purpose within the insurance industry. Danielle shares her unique transition from molecular biology to insurance, explaining how she discovered a deep appreciation for the industry’s complexity, its problem-solving capacity, and the profound meaning of helping policyholders recover during life's most challenging moments. Building on her extensive leadership experience, Danielle dives deep into practical strategies for modern sales and communication, including the power of relationship-building over purely transactional sales. She shares how to overcome common communication habits, such as over-explaining and using hedging language, while embracing the strategic power of silence, "breadcrumb conversations" for building consensus, and intentional sponsorship infrastructure to drive true workplace equity.

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.

In this episode, I interview Megan Bock, Chief Operating Officer at Federato, to discuss her fascinating 20-year career journey across traditional commercial P&C insurance and her leap into the AI-native InsurTech space. Megan shares why she ultimately stayed in the insurance industry, driven by the profound impact and promises we keep to people during their most challenging moments, and what motivated her to seek out an early-stage startup environment where her voice could be heard more loudly and her impact could be felt faster. We also dive into the realities of leadership in male-dominated industries, why authenticity always outperforms trying to fit in, and how AI is actively augmenting underwriting by handling complex data so humans can focus on relationships and strategy. Megan offers incredible, practical wisdom on building core values through employee collaboration, prioritizing high emotional intelligence and soft skills when building a dream team, and learning to delegate effectively to avoid burnout and create a more equitable playing field.

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 Stephanie Miles, Senior Vice President, Producer, and Practice Leader at Marsh McLennan Agency, for an incredible conversation about family legacies, authenticity, and redefining leadership in insurance. Stephanie shares her unique journey to the industry, stemming from a deep-rooted family history starting with her grandfather's agency in 1910, and how pivoting from retail and underwriting eventually led her to build a multi-million-dollar book of business. We dive into what it’s like being a triple threat in a male-dominated field, why selling insurance is a lot like selling a commodity like red lipstick, and how the industry can create its own "Caitlin Clark effect" by focusing on storytelling rather than changing its core. Stephanie also opens up about the realities of protecting family time as a working mother, building a true 50-50 partnership with her wife Taylor, and why ambition and prioritizing your home life can happily coexist. It’s a powerful, heartfelt discussion on ditching the corporate box, betting on yourself, and opening doors for the next generation.