InsHER

Megan Bell

InsHER Podcast is dedicated to celebrating and elevating women shaping the insurance industry. Hosted by Megan Bell, each episode features inspiring conversations with remarkable women who share their unique stories, insights, and advice. By highlighting diverse voices and experiences, the podcast fosters community, promotes leadership, and showcases the incredible impact women are making in the industry. Edited by Michael Landry.

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25 episodes
weekly
Avg 32 min
English

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S3 · E43
Wednesday · 36 min
Insurance Touches Everything: Rebekah Ratliff on Shaping the Future of the Industry
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.
S3 · E42
October 21 · 59 min
The Evolution of Executive Leadership for Women in Insurance: Sabrina Hart, Christina Colby, and Rita Jupe in Partnership with ISC Group
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.
S3 · E10
October 14 · 26 min
Time for an Upgrade: Kateryna Monastyrska on Modern Tech and Motherhood
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.
S3 · E40
October 7 · 30 min
Hair Today, Gone to a Good Cause: Natalie Golubski on Putting Others First
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.
S3 · E39
September 30 · 21 min
The Long Game: Stephanie Dewald on Leading and Losing with Grace
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.
S3 · E38
September 23 · 27 min
Talent Over Everything: Angela Ripley on Bringing Everyone Forward Together
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.
S3 · E37
September 16 · 34 min
The Business of Belonging: Susan Johnson on Results Rooted in Culture
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.
S3 · E36
September 9 · 35 min
Why Not Me? Mary O'Leary Dronson on Self-Advocacy and Owning Your Career Path
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.
S3 · E35
September 2 · 30 min
Building Sanctuary: Inside the ISC Group Community with Margaret Resce Milkint
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.
S3 · E34
August 26 · 35 min
Speak for Yourself: Danielle Clifford on Confident Communication
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.
S3 · E33
August 19 · 21 min
A Shoulder to Stand On: Shanna Sweeney on Selfless Leadership
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.
S3 · E32
August 12 · 33 min
Dropping the Act: Megan Bock on Why Authenticity Always Wins
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.
S3 · E31
August 5 · 34 min
Leadership ≠ Management: Layla Farivar on Individual Contribution
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.
S3 · E38
July 29 · 44 min
Step Out of the Box: Stephanie Miles on Not Fitting In, But Insurance Fitting Her
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.
S3 · E29
July 22 · 28 min
No Filter: Jennifer Kapp on Showcasing Reality, Not Perfection
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.
S3 · E28
July 15 · 34 min
Ready or Not: Candace Steele on Taking Career Leaps and Building Resilience
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.
S3 · E27
July 8 · 24 min
The Kids Are Alright (In the Office): Rajni Kapur on Flexibility for Paid Working Mothers
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.
S3 · E26
June 24 · 42 min
Can You Hear Me Now? Unmuting Yourself with Rachel Druckenmiller
In this episode, I interview Rachel Druckenmiller, Keynote Speaker + Founder, UNMUTED, and former Director of Well-Being and Employee Engagement at a benefits consulting firm. Rachel opens up about her unexpected 13-year journey in the insurance industry, which began as a simple summer administrative role and evolved into pioneering an award-winning corporate wellness initiative from scratch. Facing tight budgets and early resistance, Rachel shares how she and a colleague eventually built a national exemplar of workplace wellness by experimenting with innovative ideas internally before offering them to clients. She dives into the art of service differentiation, detailing how providing unique, personalized value not only cements client retention but also positions insurance professionals as indispensable industry leaders. Rachel also introduces me to the concept of "internal muting", the ways professionals, particularly women, silence their own voices due to internal, relational, or structural fears. Drawing from her own raw experience with burnout and health challenges while at the height of her corporate career, Rachel breaks down how authentic self-confidence is fundamentally rooted in self-trust. She shares actionable leadership strategies for overcoming self-silencing, including the "Reflected Best Self" feedback practice and the transformative shift of asking "what if it were just right?" instead of focusing on the worst-case scenario. What resonated most is her perspective on championing ambitious talent, not to be threatened by it. Rachel also shared these original songs! Somebody: https://song.link/somebody-rachel Believe In You: https://song.link/believeinyou
S3 · E25
June 17 · 19 min
Opening Doors: Natina Berry on Authentic and Intentional Community
In this episode, I interview Natina Berry, Senior Underwriter at Freberg Environmental, with over 20 years of expertise in commercial insurance and strategic account management. Natina shares her fascinating career journey with me, which began with a specialized training program through The Hartford. Beyond her corporate role, Natina discusses her extensive leadership in the industry, including serving as president of the NAAIA New York Tri-State Chapter and on the board of RIMS New York, explaining how getting involved in committees builds genuine confidence and visibility. Natina is also a single mother of four boys, and opens up about the "five-shift" daily structure she used to approach parenting and her career. Our conversation goes deep into the true meaning of professional development, moving past surface-level networking to focus on building authentic relationships, mentorship, and sponsorship. Natina highlights how unexpected skills, like learning to play golf, opened unique doors for connection. From inspiring the next generation at a local Girl Scouts event to preparing diverse teams for the impact of AI, Natina defines leadership as actively opening doors for others.
S3 · E24
June 10 · 26 min
D&O Your Thing: Sarah Abrams on Why the Things That Pull at You Matter
In this episode, I interview Sarah Abrams, Executive Vice President at RT ProExec and the new voice behind The D&O Diary. Sarah shares how she went from practicing law as a coverage attorney in Chicago to handling complex professional liability claims, moving into underwriting, and ultimately stepping into one of the most respected thought leadership platforms in the D&O space. Along the way, we talk about the career pivots that shaped her path, including how becoming a mother influenced her professional decisions and led her to seek new opportunities that aligned with both her ambitions and her life outside of work. We also explore the power of writing, storytelling, and thought leadership in an industry often known for its technical complexity. Sarah opens up about the honor and responsibility of co-authoring The D&O Diary, a publication she considered essential reading long before she became an author. We discuss overcoming self-doubt, handling criticism with grace, and why sharing ideas publicly can be both vulnerable and rewarding.

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